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6 pages, 1051 KiB

Open AccessProceeding Paper

Fast Phthalate Detection in Textile Samples: A LC-MS/MS Screening Method Using Precursor Ion Scans

by Natalia Aldegunde-Louzao, Manuel Lolo-Aira and Carlos Herrero-Latorre

Chem. Proc. 2024, 16(1), 1; https://doi.org/10.3390/ecsoc-28-20150 - 14 Nov 2024

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Phthalate esters (PAEs), commonly known as phthalates, are widely used as plasticizers in the textile industry to improve the flexibility, transparency, and durability of various materials. However, the potential adverse health effects associated with them (such as endocrine disruption, reproductive toxicity, and possible [...] Read more.

Phthalate esters (PAEs), commonly known as phthalates, are widely used as plasticizers in the textile industry to improve the flexibility, transparency, and durability of various materials. However, the potential adverse health effects associated with them (such as endocrine disruption, reproductive toxicity, and possible carcinogenicity) require strict control measures. In this work, a liquid chromatography–tandem mass spectrometry (LC-MS/MS) method was developed to determine phthalates in textile samples. By using precursor ion scans (specifically the precursor ion 149, characteristic of phthalates), the procedure improved the specificity of the analysis. The developed method was successfully applied to different textile samples, and the results obtained were comparable to those from the official gas chromatography method (GC-MS/MS). The proposed method enables the rapid and effective detection of phthalates in quality control laboratories within the textile industry. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 366 KiB

Open AccessProceeding Paper

In Silico Studies of Khellin and Related Furochromenes by Modified POM Analysis

by Renata Gašparová

Chem. Proc. 2024, 16(1), 2; https://doi.org/10.3390/ecsoc-28-20203 - 14 Nov 2024

Viewed by 554

Abstract

POM (Petra/Osiris/Molinspiration) analysis and related in silico tools are well-established methods used to evaluate the potential of molecules to become drug candidates by predicting their biological activity and calculating various physicochemical properties, ADME parameters, or toxicity. Khellin 1 is a well-known component of [...] Read more.

POM (Petra/Osiris/Molinspiration) analysis and related in silico tools are well-established methods used to evaluate the potential of molecules to become drug candidates by predicting their biological activity and calculating various physicochemical properties, ADME parameters, or toxicity. Khellin 1 is a well-known component of the Ammi visnaga (khella) plant used for centuries in folk medicine for the treatment of urinary tract pain associated with kidney stones. Modern medicine has found the importance of khellin in the treatment of psoriasis, angina pectoris, or vitiligo. However, the oral use of khellin is limited by its potential adverse effects, such as dizziness, constipation, headache, itching, or lack of appetite. Many natural or synthetic furopyrrole derivatives have been extensively studied and reported to possess numerous biological effects, including anticancer, anti-inflammatory, or antimicrobial. The present in silico study is aimed at revealing the most promising drug candidates based on favorable pharmacokinetic parameters and toxicological characteristics. A modified POM analysis of sixteen furochromenes was performed using Molinspiration, Osiris, and SwissADME software. Studied structures were selected due to the modifications of the khellin skeleton. Substitution of the furan or pyran ring, modification of one or both methoxy groups, or hydrogenation of one or both heterocyclic rings were included. The results of this preliminary in silico investigation suggest all furopyrroles have good oral bioavailability and a high level of gastrointestinal absorption. The bioactivity score prediction shows their ability to act predominantly as ion channel modulators or enzyme inhibitors. All compounds exhibit a low risk of being irritants; nine of them exhibit a low risk of being mutagenic, tumorigenic, or having reproductive effects. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1588 KiB

Open AccessProceeding Paper

Integrated Computational Approach to Rational Drug Design Targeting SIK2/3: From Theory to Practice

by Eid Youssef Eid Rashed and Alisa Gorislav

Chem. Proc. 2024, 16(1), 3; https://doi.org/10.3390/ecsoc-28-20241 - 15 Nov 2024

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Abstract

This study presents a comprehensive approach to designing and optimizing small molecule inhibitors targeting Salt-Inducible Kinases 2 and 3 (SIK2 and SIK3), crucial regulators of cellular signaling pathways implicated in various diseases, including cancer, inflammation, and metabolic disorders. By integrating advanced computational methods [...] Read more.

This study presents a comprehensive approach to designing and optimizing small molecule inhibitors targeting Salt-Inducible Kinases 2 and 3 (SIK2 and SIK3), crucial regulators of cellular signaling pathways implicated in various diseases, including cancer, inflammation, and metabolic disorders. By integrating advanced computational methods and expert-driven chemical synthesis, we generated a diverse library of potential inhibitors and meticulously evaluated their pharmacological properties and binding affinities to SIK2. Through a rigorous analysis of generated data and molecular docking simulations, we successfully identified lead compounds with promising therapeutic potential. Subsequently, employing iterative chemical modifications guided by human expertise, we further optimized these leads, enhancing their efficacy and specificity. Additionally, employing molecular dynamics simulations provided valuable mechanistic insights into the dynamic behavior of optimized compounds within the complex biological environment, elucidating their potential as effective inhibitors of SIK2 activity. Our findings underscore the efficacy and significance of an integrated computational and experimental approach in the development of novel therapeutics targeting SIK2 and SIK3. By bridging computational predictions with experimental validation, this approach not only accelerates the drug discovery process but also increases the likelihood of identifying clinically relevant compounds. Furthermore, the insights gained from this study lay a solid foundation for future preclinical and clinical investigations, paving the way for the development of effective treatments for diseases associated with dysregulated SIK2 and SIK3 signaling pathways. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 4197 KiB

Open AccessProceeding Paper

Molecular Docking and Dynamics of a Series of Aza-Heterocyclic Compounds Against Penicillin-Binding Protein 2a of Methicillin-Resistant Staphylococcus aureus

by Karen Astrid Ortiz-Vargas, Rsuini Uri Gutierrez-Aguilar, Judit Araceli Avina-Verduzco, Hugo A. Garcia-Gutierrez, Julio Cesar Ontiveros-Rodriguez, Rafael Herrera-Bucio and Pedro Navarro-Santos

Chem. Proc. 2024, 16(1), 4; https://doi.org/10.3390/ecsoc-28-20221 - 14 Nov 2024

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Abstract

Staphylococcus aureus is a Gram-positive bacterium known to cause mild to severe and potentially fatal infections such as endocarditis, sepsis, meningitis, pneumonia, and bacteremia, among others. The methicillin-resistant strain of Staphylococcus aureus (MRSA) arose because the bacterium acquired an additional penicillin-binding protein by [...] Read more.

Staphylococcus aureus is a Gram-positive bacterium known to cause mild to severe and potentially fatal infections such as endocarditis, sepsis, meningitis, pneumonia, and bacteremia, among others. The methicillin-resistant strain of Staphylococcus aureus (MRSA) arose because the bacterium acquired an additional penicillin-binding protein by lateral gene transfer, known as penicillin-binding protein 2a (PBP2a). It is responsible for cross-linking peptidoglycan chains in the formation of the bacterial cell wall, and it is a deathly pathogen because it can infect almost all sites in the body; thus, the development of novel PBP2a inhibitors and the treatment of infections caused by this bacterium is vital. In this work, a systematic study of molecular docking and molecular dynamics was carried out to determine the stability of a set of ligands, aza-heterocyclic compounds, against PBP2a, analyzing their RMSD, H-bonds interactions, and binding free energy. In addition, the pharmacokinetic properties are discussed, finding that our proposed ligand 5 is the most promising compound in terms of stability and energetic results. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 222 KiB

Open AccessProceeding Paper

Phytochemical Screening and Inflammatory Activity Evaluation of Hydroalcoholic Extract of Glycyrrhiza glabra Root

by Amina Tabet Zatla and Amina Hammoudi

Chem. Proc. 2024, 16(1), 5; https://doi.org/10.3390/ecsoc-28-20148 - 14 Nov 2024

Cited by 1 | Viewed by 686

Abstract

Glycyrrhiza glabra (licorice) belongs to the family Fabaceae and has a long story in traditional medicines and folk remedies to treat inflammation, arthritis, gastrointestinal problems and dyspepsia, Consequently, there is ongoing research into novel plants and herbal compounds possessing anti-inflammatory properties, aiming to [...] Read more.

Glycyrrhiza glabra (licorice) belongs to the family Fabaceae and has a long story in traditional medicines and folk remedies to treat inflammation, arthritis, gastrointestinal problems and dyspepsia, Consequently, there is ongoing research into novel plants and herbal compounds possessing anti-inflammatory properties, aiming to uncover more potent alternatives while mitigating the potential toxicities associated with conventional anti-inflammatory medications. The aim of the present study was to evaluate the anti-inflammatory activity of hydroalcoholic extract of Glycyrrhiza glabra root, in order to find new and more effective agents for the treatment of degenerative and inflammatory diseases. The anti-inflammatory activity was assessed using the protein denaturation method using the standard drug Diclofenac. The phytochemical constituents identified were flavonoids, alkaloids, phenols, saponins, steroids, and terpenoids, with flavonoids, alkaloids, and phenols being the most abundant. The results showed that the Hydroalcoholic extract of G. glabra root has a very good inhibitory effect, with percentages of 81%, at a concentration of 10 g/L compared to Diclofenac (61.3%). Hydroalcoholic extract of roots exhibit attractive anti-inflammatory properties, which can be attributed to the presence of secondary metabolites of different classes of compounds and can, therefore, be considered a promising candidate for future application as alternative therapeutic agents, particularly in the development of anti-inflammatory drugs. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

7 pages, 2990 KiB

Open AccessProceeding Paper

A Case Study on Utilising Soy and Whey Protein Polymers: Advances in Enteric Coatings for Improved Delayed-Release Pharmaceuticals

by Enas Bshena, Abdalrahem Shtawa, Sarra Takita and Magdi Mussa

Chem. Proc. 2024, 16(1), 6; https://doi.org/10.3390/ecsoc-28-20156 - 14 Nov 2024

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Abstract

An enteric coating plays a crucial role in preventing the disintegration of pharmaceutical dosage forms in the stomach. This is particularly important for drugs unstable at an acidic pH or designed to act in the small intestine. While conventional synthetic polymers have been [...] Read more.

An enteric coating plays a crucial role in preventing the disintegration of pharmaceutical dosage forms in the stomach. This is particularly important for drugs unstable at an acidic pH or designed to act in the small intestine. While conventional synthetic polymers have been widely used for enteric coatings, there is growing interest in exploring naturally derived proteins as an alternative. This study focused on two natural polymers: soy protein and whey protein isolates, first by determining the gastro-resistance properties of films prepared from these proteins. Then, appropriate casting solutions were developed to create polymeric films, and their resistance to acidic pH was evaluated using disintegration tests. Second, crate drug pellets coated with the most effective protein-based film were previously prepared, and their performance was assessed using the USP apparatus I (basket). The results demonstrated that the coated pellets (SA and SAG) exhibited excellent gastro-resistance properties. Specifically, the percentage release of the coated pellets met the USP criteria: less than 10% release in the first 2 h under acidic conditions, followed by at least 80% release within 45 min in the buffer phase. In contrast, uncoated pellets showed immediate release, with over 69% of the dye released during the initial 2 h. Notably, the SA and SAG-coated pellets demonstrated remarkable resistance to acidic pH, releasing only 1% and approximately 2% of the dye faster than uncoated pellets. These findings highlight the potential of SA and SAG coating films for efficient delayed release or enteric coating applications. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1422 KiB

Open AccessProceeding Paper

A Computational and Spectroscopic Approach to Elucidate the Coordination Structures in Iron–Catechol Polymers

by Matías Capurso, Gabriel Radivoy, Fabiana Nador and Viviana Dorn

Chem. Proc. 2024, 16(1), 7; https://doi.org/10.3390/ecsoc-28-20208 - 14 Nov 2024

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Abstract

Coordination polymer particles (CPPs) with catechol functionalities present significant potential for various applications. To elucidate their structural features, we synthesized CPPs using bidentate bis-catechol and catechol–pyridine ligands and employed both computational and spectroscopic techniques. The results reveal distinct coordination environments: a four-center coordination [...] Read more.

Coordination polymer particles (CPPs) with catechol functionalities present significant potential for various applications. To elucidate their structural features, we synthesized CPPs using bidentate bis-catechol and catechol–pyridine ligands and employed both computational and spectroscopic techniques. The results reveal distinct coordination environments: a four-center coordination for catechol–catechol and an octahedral coordination for catechol–pyridine. Experimental UV-Vis, IR, and Raman spectroscopic analyses confirmed these findings, further supporting the accuracy of the computational model. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 410 KiB

Open AccessProceeding Paper

Activity of Satureja montana Allelochemical Volatiles Against the Pinewood Nematode

by Gonçalo Pereira and Jorge M. S. Faria

Chem. Proc. 2024, 16(1), 8; https://doi.org/10.3390/ecsoc-28-20154 - 14 Nov 2024

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Abstract

Essential oils (EOs) are complex mixtures of mainly volatile terpenes and phenylpropanoids with strong biological activities. Screening their nematicidal activity against plant parasitic nematodes can yield important information on anti-nematodal chemical structures. In previous studies, the EO of winter savory, Satureja montana, [...] Read more.

Essential oils (EOs) are complex mixtures of mainly volatile terpenes and phenylpropanoids with strong biological activities. Screening their nematicidal activity against plant parasitic nematodes can yield important information on anti-nematodal chemical structures. In previous studies, the EO of winter savory, Satureja montana, revealed a high nematicidal activity against the pinewood nematode (PWN), a dangerous phytoparasite that attacks pine trees and causes pine wilt disease (PWD). Its activity was solely attributed to the oxygen-containing molecules; however, interactions between EO compounds were not fully ascertained. In the present study, the main compounds of winter savory EO were tested solely and in combination to understand which were responsible for the nematicidal strength of the EO. The main EO compound, carvacrol, induced the strongest activities; however, γ-terpinene and p-cymene appear to influence its activity, even though they promote a low PWN mortality. Uncovering the interactions between the components of nematicidal EOs can provide clues to better formulate sustainable alternatives to traditional pesticides. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1848 KiB

Open AccessProceeding Paper

Evaluation the Electronic Properties of Glu-Ureido Template via Ab-Initio Study as Target Specific for PSMA

by Mohd. Faheem, Vaibhav Pandey, Anjli Shrivastav, Manisha Prasad and Manish Dixit

Chem. Proc. 2024, 16(1), 9; https://doi.org/10.3390/ecsoc-28-20204 - 14 Nov 2024

Viewed by 374

Abstract

The Prostate cancer (PC) is a major problem all over worldwide and this is the second highest cancer-related mortality rate after lung cancer all over worldwide. At least 299,010 likely cases in men were reported in the US in 2024 and about 35,250 [...] Read more.

The Prostate cancer (PC) is a major problem all over worldwide and this is the second highest cancer-related mortality rate after lung cancer all over worldwide. At least 299,010 likely cases in men were reported in the US in 2024 and about 35,250 deaths are reported. The overexpression of prostate-specific membrane antigen (PSMA) is a key factor in the progression of prostate cancer and contributes to metastasis in lymph nodes, soft tissues and bones metastasis. The numerous studies have reported that, Glu-ureido-based molecules exhibit high binding affinity for PSMA. The earliest imaging agents developed from this structure were labeled with radioactive halogen isotopes and demonstrated nanomolar binding affinity, leading to exceptional imaging properties. Hence the Glu-ureido chemical moiety is a very important template as inhibitor of PSMA. In this study to explore the chemical structural and electronic features of Glu-Ureido structure with the aid of quantum chemistry computer simulations. In this study, first optimized the structure of this chemical structure using the B3LYP 6311-G (++, d, p) basis set. In this study investigated the maximal quantity of electronic charge transfer (N_max), chemical hardness (η), electrostatic potential, chemical potential (µ) and electrophilicity (ω). By the using Natural Bond Orbital (NBO) analysis, the examination shows that the molecule’s chemically active regions π-electron-electron delocalization within the molecule that contribute to its stability. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1637 KiB

Open AccessProceeding Paper

Bioinformatics Approaches for Molecular Characterization of CT670 Hypothetical Protein of Chlamydia pneumoniae

by Abu Saim Mohammad Saikat, Tazin Afrose, Umme Saoda, Kazi Nur Uddin, Mir Monir Hossain and Md. Lutful Kabir

Chem. Proc. 2024, 16(1), 10; https://doi.org/10.3390/ecsoc-28-20207 - 14 Nov 2024

Viewed by 463

Abstract

Researchers have linked Chlamydia pneumoniae (C. pneumoniae), a type of bacteria that cannot survive outside of cells and is resistant to Gram staining, to many autoimmune diseases. People hypothesized that C. pneumoniae had a harmful function due to its tendency to [...] Read more.

Researchers have linked Chlamydia pneumoniae (C. pneumoniae), a type of bacteria that cannot survive outside of cells and is resistant to Gram staining, to many autoimmune diseases. People hypothesized that C. pneumoniae had a harmful function due to its tendency to inhabit human endothelium and epithelial tissue. This study implemented multiple bioinformatics tools and databases to understand the possible function of the CT670 hypothetical protein of C. pneumoniae. The physicochemical parameters showed the protein’s half-life in different media. These parameters also displayed the protein’s theoretical isoelectric point, aliphatic index, GRAVY value, extinction coefficient, instability index, and the amino acids and atoms that it comprises. Amino acid composition measured the percentage of amino acids present in the selected protein, with glutamate demonstrated as the greatest proportion. Moreover, hydrogen was the most abundant ratio in terms of the atomic composition of the protein, followed by carbon, oxygen, nitrogen, and sulfur. The PPI networks reveal its potential primary and secondary interactions with other proteins. We modeled and assessed the secondary and tertiary structures to understand the nature of the selected protein. Computational functional analysis predicted that the protein would be a chaperone effector. By designing and developing drugs and vaccines, we can use this protein as a target for further analysis to combat diseases caused by C. pneumoniae. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 878 KiB

Open AccessProceeding Paper

In Silico Study of FDA-Approved Drugs on Leishmania infantum CYP51, a Drug Repositioning Approach in Visceral Leishmaniasis

by Juan Diego Guarimata and Martin Lavecchia

Chem. Proc. 2024, 16(1), 11; https://doi.org/10.3390/ecsoc-28-20201 - 14 Nov 2024

Viewed by 553

Abstract

The main priority in leishmaniasis-endemic countries is to find safer and more accessible treatments for this neglected disease. In this study, we focus on a drug repositioning strategy using molecular docking. New molecular entities (NMEs) approved by the FDA from 2019 to the [...] Read more.

The main priority in leishmaniasis-endemic countries is to find safer and more accessible treatments for this neglected disease. In this study, we focus on a drug repositioning strategy using molecular docking. New molecular entities (NMEs) approved by the FDA from 2019 to the present were analyzed. The therapeutic target was the sterol 14-alpha demethylase from Leishmania infantum. Of the 125 NMEs tested, 16 demonstrated greater affinity in virtual screening than the co-crystallized inhibitor (fluconazole). This approach offers a promising method for identifying new uses for existing drugs and provides a rapid way to discover safer treatments for leishmaniasis. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 322 KiB

Open AccessProceeding Paper

Catalytic Cyclocodimerization of Silicon-Containing 1,2-Dienes with 1,3,5-Cycloheptatriene in the Synthesis of Biologically Active Bicyclo[4.2.1]Nona-2,4-Dienes

by Gulnara N. Kadikova

Chem. Proc. 2024, 16(1), 12; https://doi.org/10.3390/ecsoc-28-20107 - 4 Dec 2024

Viewed by 644

Abstract

The [6+2] cycloaddition of (2-butyl-2,3-butadienyl)(trimethyl)silane and 2,3-butadienyl(trimethyl)silane to 1,3,5-cycloheptatriene was studied using titanium- and cobalt-containing multicomponent catalytic systems: R₂TiCl₂-R’_nAlCl_3-n (R = acac, PrⁱO, Bu^tO, Cl; R’ = Et, Buⁱ, [...] Read more.

The [6+2] cycloaddition of (2-butyl-2,3-butadienyl)(trimethyl)silane and 2,3-butadienyl(trimethyl)silane to 1,3,5-cycloheptatriene was studied using titanium- and cobalt-containing multicomponent catalytic systems: R₂TiCl₂-R’_nAlCl_3-n (R = acac, PrⁱO, Bu^tO, Cl; R’ = Et, Buⁱ, n = 2, 3) and CoX₂(Y)/Z/ZnI₂ (X = acac, Br, I, Cl, OAc; Y = dppe, dppm, dppp, dppb, Ph₃P, P(OPrⁱ)₃, P(OPh)₃; Z = Zn, Mg, In, Bu₄NBH₄). The work investigated the influence of the nature of the central atom of the catalyst, the ligand environment of the catalyst, the nature of the organoaluminum cocatalyst, the reducing agent, the effect of temperature, as well as the nature of the solvent on the yield and stereoselectivity of the formation of cycloadducts. Catalytic cyclocodimerization occurs with the formation of silicon-containing bicyclo[4.2.1]nona-2,4-dienes, which are of interest as promising precursor compounds in the synthesis of new drugs. It is known that many bridged carbo- and heterocarbocyclic compounds containing silicon atoms in the structure have diverse biological activities and are valuable drugs. Based on this, the work for the first time carried out a comprehensive study of the antitumor activity of synthesized silicon-containing bicyclo[4.2.1]nona-2,4-dienes in vitro using various tumor cell lines (U937, K562, Jurkat, HL60) and normal fibroblasts. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1857 KiB

Open AccessProceeding Paper

Computational Investigations on Phycocyanobilin

by Matteo Gigli, Matteo Donati, Massimo Sgarzi and Marco Bortoluzzi

Chem. Proc. 2024, 16(1), 13; https://doi.org/10.3390/ecsoc-28-20202 - 14 Nov 2024

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Abstract

Phycocyanobilin was computationally investigated by means of DFT calculations in combination with implicit solvation starting from X-ray data. Different conformations and degrees of protonation were considered, and the acidity constants were estimated. The computed data suggest a syn-syn-syn conformation [...] Read more.

Phycocyanobilin was computationally investigated by means of DFT calculations in combination with implicit solvation starting from X-ray data. Different conformations and degrees of protonation were considered, and the acidity constants were estimated. The computed data suggest a syn-syn-syn conformation for the molecule, with the two carboxylic groups deprotonated under physiological conditions and weak acidic behavior of one of the pyrrolone heterocycles. The absorption transitions in the visible range were studied by means of TD-DFT calculations, focusing on the molecular orbitals involved. The frontier orbitals have a dominant role in the lowest energy absorption. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1188 KiB

Open AccessProceeding Paper

Synthesis of Hydrazones of Strained Polycyclic Hydrocarbons, Promising Building Blocks in Organic Chemistry

by Arslan R. Akhmetov, Zarema R. Sadretdinova, Arthur A. Khuzin, Liliya L. Khuzina and Rishat I. Aminov

Chem. Proc. 2024, 16(1), 14; https://doi.org/10.3390/ecsoc-28-20102 - 14 Nov 2024

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Abstract

For the first time, the synthesis of unsubstituted hydrazones based on various strained polycyclic hydrocarbons, namely exo-exo-4-exo-acetoxypentacyclo[8.2.1.1^5,8.0^2,9.0^3,7]tetradecane, endo-endo-4-exo-acetoxypentacyclo[8.2.1.1^5,8.0^2,9.0^3,7]tetradecane and acetoxyhexacyclo[9.2.1.0^2,7.0^3,5.0^4,8.0^9,13]tetradecane, was carried out in four stages with high yields and selectivity. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1317 KiB

Open AccessProceeding Paper

Chemoproteomic Study of Effect of Halogenated Hydroxynaphthalenecarboxanilides on Staphylococcus aureus

by Lucia Vrablova, Petra Majerova, Dominika Pindjakova, Tomas Gonec, Andrej Kovac, Alois Cizek and Josef Jampilek

Chem. Proc. 2024, 16(1), 15; https://doi.org/10.3390/ecsoc-28-20152 - 14 Nov 2024

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Abstract

Recently reported multihalogenated (CF₃/Cl) anilides of 1-hydroxynaphthalene-2-carboxanilides showed significant activity against both the reference strain Staphylococcus aureus ATCC 29213 and clinical isolates of methicillin-resistant S. aureus (MRSA). This fact inspired further investigation of the effect of these compounds on staphylococci. Chemoproteomics [...] Read more.

Recently reported multihalogenated (CF₃/Cl) anilides of 1-hydroxynaphthalene-2-carboxanilides showed significant activity against both the reference strain Staphylococcus aureus ATCC 29213 and clinical isolates of methicillin-resistant S. aureus (MRSA). This fact inspired further investigation of the effect of these compounds on staphylococci. Chemoproteomics is a tool for investigating protein targets of potential drugs. It makes it possible to understand the effect of a bioactive molecule on a living system. An activity-based protein profiling (ABPP) method was employed using highly active and inactive ring-substituted 1-hydroxynaphthalene-2-carboxanilides as probes. The experiment was performed on the universally sensitive collection strain S. aureus ATCC 29213. Tryptic cleavage of proteins was performed prior to HPLC-MS/MS analysis. Protein profiles of control samples (S. aureus cells) and profiles of S. aureus treated with inactive/active derivatives were investigated and compared to one another. More than 1000 proteins were analyzed, with approximately 70% of the proteins increased and 30% of the proteins decreased after treatment with the investigated compounds. Treatment with the inactive compound mainly resulted in the expression of various proteins, so it can be assumed that the changes in the protein profile did not affect the basic biochemical pathways or that the microorganism was able to adapt by activating other pathways/expressing other proteins, surviving. Treatment with the highly active agent resulted in much smaller proteomic changes (mainly, the inhibition of several proteins compared to the inactive compound), and S. aureus failed to adapt and was killed. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1764 KiB

Open AccessProceeding Paper

Evaluation Electronic Properties of Rufinamide via Ab-Initio Study as Anti-Epileptic Drug

by Vaibhav Pandey, Mohd. Faheem, Sachin Ranjan and Manish Dixit

Chem. Proc. 2024, 16(1), 16; https://doi.org/10.3390/ecsoc-28-20205 - 14 Nov 2024

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Abstract

The FDA approved rufinamide, chemically 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide, a triazole-based scaffold, as an anticonvulsant drug in 2008. It is mainly used to treat seizures associated with Lennox–Gastaut Syndrome (LGS). The exact mechanism of rufinamide is unknown, but some literature reported that rufinamide works by regulating [...] Read more.

The FDA approved rufinamide, chemically 1-(2,6-difluorobenzyl)-1H-1,2,3-triazole-4-carboxamide, a triazole-based scaffold, as an anticonvulsant drug in 2008. It is mainly used to treat seizures associated with Lennox–Gastaut Syndrome (LGS). The exact mechanism of rufinamide is unknown, but some literature reported that rufinamide works by regulating the brain’s sodium channel activity, which aids in maintaining the stability of neuronal membranes and averting the overabundance of electrical activity. In the view of computational chemistry, the amide group, fluorine atom, and triazole ring are the specific parts of this skeleton and play an important role in action with the receptor. This study explored computerized simulations of quantum chemistry techniques to investigate the chemical structure and electrical properties of rufinamide. An optimizing structure started the quantum calculation through the B3LYP 6311-G (++, d, p) basis set, explored along with investigating the maximal quantity of electronic charge transfer (N_max), chemical hardness (η), electrostatic potential, chemical potential (µ), and electrophilicity (ω). The Natural Bond Orbital (NBO) analysis-based observation reveals that the molecule’s chemically active regions have hyperconjugated electron interactions within the molecule, which contributes to the molecule’s stability. This study explores the role of the amide group and difluoro-substituted phenyl group in chemical structure and in binding property with the receptor of the Ca²⁺–and voltage-activated K⁺ channel. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1345 KiB

Open AccessProceeding Paper

Anti-Helicobacter Pylori Activity of Phytochemicals from Artocarpus spp.: In Silico Analysis

by Susmita Yadav and Anima Pandey

Chem. Proc. 2024, 16(1), 17; https://doi.org/10.3390/ecsoc-28-20200 - 14 Nov 2024

Viewed by 371

Abstract

Peptic ulcer disease, affecting up to 20% of the global population, poses a significant health challenge with limited treatment options due to side effects and the inefficiency of existing drugs. This study explores the potential of penicillin-binding proteins (PBPs) as targets for peptic [...] Read more.

Peptic ulcer disease, affecting up to 20% of the global population, poses a significant health challenge with limited treatment options due to side effects and the inefficiency of existing drugs. This study explores the potential of penicillin-binding proteins (PBPs) as targets for peptic ulcer treatment. PBPs, critical for bacterial cell wall integrity, are inhibited by beta-lactam antibiotics, leading to bacterial vulnerability. Flavonoids, prominent in plants, exhibit antimicrobial and gastroprotective properties against peptic ulcers. A docking analysis of 35 phytochemicals from the Artocarpus plant against PBP (PDB code: 1QMF) revealed artocarpin as a promising candidate (docking score: −148.24 Kcal/mol). Artocarpin exhibited interactions with key amino acids and demonstrated favourable in silico pharmacokinetics, including high absorption and good drug-likeness. Additionally, engeletin 5 and rutin showed significant docking scores (−134.89 and −148.07 kcal/mol, respectively). Artocarpin, identified as a potential H. pylori inhibitor, presents a promising avenue for peptic ulcer treatment, warranting further exploration of its therapeutic application. This study contributes valuable insights into the molecular interactions of phytochemicals with PBPs, paving the way for novel and effective approaches in peptic ulcer therapy. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1114 KiB

Open AccessProceeding Paper

Synthesis of New O- and S-Containing Polyheteroatomic Systems Based on 3-Substituted Pyran-2-Ones with Lawesson’s Reagent

by Dinara Ch. Kurenkova, Ekaterina M. Arzyamova, Olga A. Mazhukina and Alevtina Yu. Yegorova

Chem. Proc. 2024, 16(1), 18; https://doi.org/10.3390/ecsoc-28-20106 - 9 Dec 2024

Viewed by 531

Abstract

In recent years, Lawesson’s reagent has been explored for the synthesis of both open-chain P,S-containing derivatives and P,S-heterocyclic systems, with potential biological activity. The character of the interaction between arylmethylene-2H-pyran-2-ones and Lawesson’s reagent depends on the structure and position of the substituent in [...] Read more.

In recent years, Lawesson’s reagent has been explored for the synthesis of both open-chain P,S-containing derivatives and P,S-heterocyclic systems, with potential biological activity. The character of the interaction between arylmethylene-2H-pyran-2-ones and Lawesson’s reagent depends on the structure and position of the substituent in the aromatic ring of the substrate and on the polarity of the reaction medium. Three main pathways were shown to be realized for this group of compounds. In the absence of a substituent in the ring, the reaction proceeds as a classical thionation followed by S-heterocyclization. In the presence of the electron-withdrawing group, the enol form of the substrate is stabilized, which promotes the formation of a new pyran ring or a phosphorus-sulfur-organic compound. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 828 KiB

Open AccessProceeding Paper

The Formation of a Biosensor Based on Urease Immobilized in the “Bovine Serum Albumin–Safranin–Fullerene” Composite for the Determination of Urea

by Anna Kharkova, Tatyana Lavrova and Maria Gertsen

Chem. Proc. 2024, 16(1), 19; https://doi.org/10.3390/ecsoc-28-20191 - 14 Nov 2024

Viewed by 303

Abstract

Urea, the end product of protein breakdown, is crucial for detecting chronic conditions. Normal urine urea levels range from 110 to 390 mM. This project aims to create a biosensor for rapid urea monitoring using urease immobilized on bovine serum albumin (BSA), safranin [...] Read more.

Urea, the end product of protein breakdown, is crucial for detecting chronic conditions. Normal urine urea levels range from 110 to 390 mM. This project aims to create a biosensor for rapid urea monitoring using urease immobilized on bovine serum albumin (BSA), safranin (SAF), and fullerene. The biosensor features a modified graphite paste electrode with a bionanocomposite, a silver chloride reference electrode, and a potentiostat set at +0.275 V. The sensor accurately measures urea concentrations from 68 to 410 mM in urine. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1291 KiB

Open AccessProceeding Paper

Investigating the Molecular Interactions of Thymol and Menthol as Green Solvents Using Density Functional Theory Methods

by Mehdi Hammar, Nasséra Benbrahim and Amina Negadi

Chem. Proc. 2024, 16(1), 20; https://doi.org/10.3390/ecsoc-28-20213 - 14 Nov 2024

Viewed by 438

Abstract

This research focuses on the study of molecular interactions between two systems known as natural green solvents, thymol and menthol. Their reputation is based on their broad applications in disinfection and consumer products. This analysis concerns the behaviors of these two molecules in [...] Read more.

This research focuses on the study of molecular interactions between two systems known as natural green solvents, thymol and menthol. Their reputation is based on their broad applications in disinfection and consumer products. This analysis concerns the behaviors of these two molecules in the form of dimers. Density Functional Theory (DFT) methods are used in this context. The results show significant interactions between molecules and can help to understand the behavior of one in the presence of the other. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1202 KiB

Open AccessProceeding Paper

Optimizing Germanium-Selective Functionalization on Patterned SiGe Substrates with Thiol-Based Molecules: The Critical Role of Oxygen-Free Conditions

by Alessia Arrigoni, Federico Turco, Benedetta Maria Squeo, Sonia Freddi, Monica Bollani, Tersilla Virgili, Andrea Chiappini, Laura Pasquardini and Mariacecilia Pasini

Chem. Proc. 2024, 16(1), 21; https://doi.org/10.3390/ecsoc-28-20193 - 9 Dec 2024

Cited by 1 | Viewed by 598

Abstract

Germanium offers attractive optical properties despite being an indirect bandgap semiconductor, and new Ge-based devices are being optimized for sensing and photonics applications. In particular, considering the use of Ge as a sensor, improving its selectivity via organic grafting offers new alternatives that [...] Read more.

Germanium offers attractive optical properties despite being an indirect bandgap semiconductor, and new Ge-based devices are being optimized for sensing and photonics applications. In particular, considering the use of Ge as a sensor, improving its selectivity via organic grafting offers new alternatives that are still under investigation. In this work, we focus on the selective functionalization of germanium in SiGe-patterned alloys using a custom thiol-based luminescent molecule, namely 6-[2,7-bis[5-(5-hexyl-2-thienyl)-2-thienyl]-9-(6-sulfanylhexyl)fluoren-9-yl]hexane-1-thiol. The process selectively targets regions with Ge, while leaving Si-rich areas uncovered. Moreover, this study emphasizes the importance of an oxygen-free environment, as performing the functionalization in an inert atmosphere significantly improves surface coverage. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1035 KiB

Open AccessProceeding Paper

Structural Analogues of Thyronamines: Some Aspects of the Structure and Bioactivity of 4-[4-(2-Aminoetoxy)benzyl]aniline

by Alexander B. Eresko, Elena V. Raksha, Dmitry A. Filimonov, Nadezhda N. Trubnikova, Irina A. Kisilenko and Dorota M. Chudoba

Chem. Proc. 2024, 16(1), 22; https://doi.org/10.3390/ecsoc-28-20165 - 14 Nov 2024

Viewed by 346

Abstract

Molecular modelling of the structure and evaluation of the chemical shifts of ¹H and ¹³C nuclei were performed for the 4-[4-(2-aminoethoxy)benzyl]aniline, which is a structural analogue of thyronamines. The intramolecular dynamics of the key structural fragments of 4-[4-(2-aminoethoxy)benzyl]aniline were studied by [...] Read more.

Molecular modelling of the structure and evaluation of the chemical shifts of ¹H and ¹³C nuclei were performed for the 4-[4-(2-aminoethoxy)benzyl]aniline, which is a structural analogue of thyronamines. The intramolecular dynamics of the key structural fragments of 4-[4-(2-aminoethoxy)benzyl]aniline were studied by the PM6-DH2 method as well as at the B3LYP/6-31G(d,p) level of theory. Nonspecific solvation with dimethyl sulfoxide was taken into account within the polarized continuum model. Specific solvation by one and two DMSO molecules was considered within supermolecule approximation. Chemical shifts of the ¹H and ¹³C nuclei were estimated for the most stable conformer of 4-[4-(2-aminoethoxy)benzyl]aniline as well as for its solvates with DMSO. Calculated chemical shifts of the ¹H and ¹³C nuclei are in good agreement with the experimental ones obtained for 4-[4-(2-aminoethoxy)benzyl]aniline in DMSO-d₆ solution. Some aspects of the bioactivity of 4-[4-(2-aminoethoxy)benzyl]aniline are discussed. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 2232 KiB

Open AccessProceeding Paper

Synthesis and Spectral Properties of a New Spirophotochromic Molecule

by Artur Khuzin and Liliya Khuzina

Chem. Proc. 2024, 16(1), 23; https://doi.org/10.3390/ecsoc-28-20103 - 14 Nov 2024

Viewed by 282

Abstract

Due to their ability to reversibly isomerize under the influence of external stimuli, spiropyrans represent the most interesting class of organic photochromic molecules. The photochromic properties of the isomeric forms of spiropyrans differ significantly from each other, which makes it possible to use [...] Read more.

Due to their ability to reversibly isomerize under the influence of external stimuli, spiropyrans represent the most interesting class of organic photochromic molecules. The photochromic properties of the isomeric forms of spiropyrans differ significantly from each other, which makes it possible to use these photochromes as sensors, optoelectronic and holographic devices, memory elements, etc. Also, an undoubted advantage of spiropyrans compared to other classes of organic photochromes is the relative ease of their preparation and chemical transformation. At the same time, modification of the structure of spiropyrans by introducing various functional groups opens up great synthetic possibilities for obtaining new photochromic molecules with various spectral-kinetic characteristics. In the development of research aimed at expanding the boundaries of the use of spirophotochromic compounds, in order to obtain new light-controlled materials with different characteristics, as well as to study the influence of functional groups in the spirophotochromic molecule on the spectral and photochromic properties, we have synthesized a new spiropyran. In this work, we synthesized a new salt of photochromic spiropyran containing various functional groups (–CHO, –NO₂, –OCH₃, –(CH₂)₅N(CH₃)₂*HBr), capable of reversibly responding to external influences. Photoinduced transformations and the spectral and kinetic characteristics of the synthesized compound were studied. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1105 KiB

Open AccessProceeding Paper

1,3-Dipolar Cycloaddition Reactions of 2-Arylmethylidentiazolo[3,2-a]pyrimidines with Azomethinylides: Studying the Supramolecular Organization of Products in the Crystalline Phase

by Anna Nefedova, Darya Tretyakova, Dilyara Mingazhetdinova, Artem Agarkov, Alexander Ovsyannikov, Igor Litvinov, Svetlana Solovieva and Igor Antipin

Chem. Proc. 2024, 16(1), 24; https://doi.org/10.3390/ecsoc-28-20098 - 14 Nov 2024

Viewed by 332

Abstract

The [3+2]-cycloaddition of azomethinylides formed in situ to dipolarophiles is a promising approach for the synthesis of dispyroderivatives of oxindole and acenaphthenedione. In the course of our studies, it was shown that the cycloaddition of azomethinylides occurs specifically through the exocyclic double C=C [...] Read more.

The [3+2]-cycloaddition of azomethinylides formed in situ to dipolarophiles is a promising approach for the synthesis of dispyroderivatives of oxindole and acenaphthenedione. In the course of our studies, it was shown that the cycloaddition of azomethinylides occurs specifically through the exocyclic double C=C bond resulting in the formation of a new pyrrolidine cycle as part of the molecule and, consequently, a dispyroheterocycle. This work is devoted to the synthesis and structural analysis of dispyrothiazolo[3,2-a]pyrimidine in the crystalline phase. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 686 KiB

Open AccessProceeding Paper

Artificial Intelligence for Alzheimer’s Disease Detection: Enhancing Biomarker Analysis and Diagnostic Precision

by Richa Gupta and Zoya Iftekhar

Chem. Proc. 2024, 16(1), 25; https://doi.org/10.3390/ecsoc-28-20206 - 14 Nov 2024

Viewed by 977

Abstract

Alzheimer’s disease (AD) is a progressive neurodegenerative disorder characterized by cognitive decline and memory impairment. Early and accurate detection of AD is crucial for timely intervention and effective treatment. Biomarkers such as amyloid-beta and tau proteins, genetic markers like the APOE genotype, and [...] Read more.

Alzheimer’s disease (AD) is a progressive neurodegenerative disorder characterized by cognitive decline and memory impairment. Early and accurate detection of AD is crucial for timely intervention and effective treatment. Biomarkers such as amyloid-beta and tau proteins, genetic markers like the APOE genotype, and neuroimaging findings are essential for AD diagnosis and prognosis, but their complex interactions require advanced analytical tools. AI has emerged as a transformative tool in healthcare, offering advanced computational techniques to analyze complex biomarker data with enhanced precision. This review paper explores the advancements in diagnosing Alzheimer’s disease (AD) using artificial intelligence (AI) techniques. In the paper, we discuss the importance of diagnosing AD accurately and the potential benefits of using AI techniques for the early and accurate detection of AD. We emphasize the significance of AI in optimizing biomarker analysis for AD detection, discussing the challenges in their implementation and future implications. AI technologies can transform AD detection by significantly improving diagnostic imaging techniques, identifying key biomarkers, and standardizing the analysis of complex neuroimaging data. In this paper, we also highlight the critical role of AI in addressing challenges associated with integrating new technologies into clinical practice and providing effective solutions for consistent and reliable AD detection techniques. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1147 KiB

Open AccessProceeding Paper

Hydro-Lipophilic Properties of Chlorinated and Brominated 1-Hydroxynaphthalene-2-Carboxanilides

by Lucia Vrablova, Tomas Gonec and Josef Jampilek

Chem. Proc. 2024, 16(1), 26; https://doi.org/10.3390/ecsoc-28-20151 - 14 Nov 2024

Viewed by 275

Abstract

1-Hydroxy-N-phenylnaphthalene-2-carboxamide and a series of seventeen other carboxanilides in the anilide part of dichlorinated, trichlorinated, dibrominated, tribrominated, and chlorinated/brominated variants have recently been reported as biologically active compounds mainly with antibacterial, antimycobacterial, and anticancer effects. Since lipophilicity is one of the [...] Read more.

1-Hydroxy-N-phenylnaphthalene-2-carboxamide and a series of seventeen other carboxanilides in the anilide part of dichlorinated, trichlorinated, dibrominated, tribrominated, and chlorinated/brominated variants have recently been reported as biologically active compounds mainly with antibacterial, antimycobacterial, and anticancer effects. Since lipophilicity is one of the factors influencing the bioavailability (absorption, distribution, metabolism, and elimination), activity, and even toxicity of bioactive compounds, all the derivatives were investigated for their lipophilic and hydrophilic properties. All eighteen compounds were analyzed by reversed-phase high-performance liquid chromatography (RP-HPLC). The procedure was performed under isocratic conditions with methanol as the organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. The lipophilicity values are expressed as the logarithm of the capacity factor k (for the mobile phase water/methanol) and the distribution coefficients D at pH values of 6.5 and 7.4 (for the mobile phase buffer/methanol), as well as the calculated values of log P/Clog P by various methods. 1-Hydroxy-N-(3,4,5-trichlorophenyl)naphtha- lene-2-carboxamide and N-(4-bromo-3-chlorophenyl)-1-hydroxynaphthalene-2-carboxamide are the most lipophilic compounds of the whole series; on the other hand, surprisingly, unsubstituted 1-hydroxy-N-phenylnaphthalene-2-carboxamide is not the least lipophilic derivative. The mutual correlations between the experimental and predicted lipophilicity values are low; in addition, there are large deviations in the cross-correlations between log k and log D, which are due to the presence of a free ionizable phenolic group in the molecule. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1316 KiB

Open AccessProceeding Paper

DFT Studies on Physicochemical Properties and Spectral Data of 2-Thiophene Carboxylic Acid Thiourea Derivatives

by Andreea Neacsu, Carmellina Badiceanu, Cristina Stoicescu and Viorel Chihaia

Chem. Proc. 2024, 16(1), 27; https://doi.org/10.3390/ecsoc-28-20214 - 14 Nov 2024

Cited by 1 | Viewed by 331

Abstract

This study focused on examining five synthesized 2-thiophene carboxylic acid thiourea derivatives that have significant pharmaceutical applications. These compounds exhibit antibacterial properties against both bacterial and fungal strains. In this study, density functional theory (DFT) calculations were performed, and the electronic properties of [...] Read more.

This study focused on examining five synthesized 2-thiophene carboxylic acid thiourea derivatives that have significant pharmaceutical applications. These compounds exhibit antibacterial properties against both bacterial and fungal strains. In this study, density functional theory (DFT) calculations were performed, and the electronic properties of the investigated compounds, such as ionization potential, electron affinity, and electronic excitation energies, were calculated and compared to determine the beneficial features of these potential future medications. A vibrational analysis of the considered structures was performed, and the experimental FT-IR ATR spectra of the solid powders are presented. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1209 KiB

Open AccessProceeding Paper

One-Pot Synthesis of Imidazo[1,2-a]pyridines via Groebke–Blackburn–Bienaymé Reaction and CuAAC Assisted by MW

by Manuel A. Rentería-Gómez, David Calderón-Rangel, Fidel Rodríguez-López, Alejandro Corona-Díaz and Rocío Gámez-Montaño

Chem. Proc. 2024, 16(1), 28; https://doi.org/10.3390/ecsoc-28-20190 - 14 Nov 2024

Viewed by 380

Abstract

Bis-heterocyclic compounds containing imidazo[1,2-a]pyridines (IMPs) are privileged heterocyclic drug scaffolds due to their potential applications. The Groebke–Blackburn–Bienaymé reaction (GBBR) is a greener alternative to synthesizing IMPs. On the other hand, 1,2,3-triazole scaffolds are biososteres of the trans amide, and their incorporation [...] Read more.

Bis-heterocyclic compounds containing imidazo[1,2-a]pyridines (IMPs) are privileged heterocyclic drug scaffolds due to their potential applications. The Groebke–Blackburn–Bienaymé reaction (GBBR) is a greener alternative to synthesizing IMPs. On the other hand, 1,2,3-triazole scaffolds are biososteres of the trans amide, and their incorporation in bioactive molecules provides advantages such as resistance to cleavage mediated by proteases and improved stability. In this context, the CuAAC reaction is the most efficient approach to synthesizing 1,4-disustituted-1,2,3-triazoles. Herein, we describe a novel one-pot synthesis of IMPs by the GBBR-CuAAC strategy assisted by microwave irradiation. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 2404 KiB

Open AccessProceeding Paper

Microwave-Assisted Green Synthesis of Binary/Ternary Zn_xCo_1−xFe₂O₄ (x = 0, 0.5, 1) Nanoparticles

by Sanaz Chamani and Masoumeh Khatamian

Chem. Proc. 2024, 16(1), 29; https://doi.org/10.3390/ecsoc-28-20248 - 15 Nov 2024

Viewed by 417

Abstract

In this study, magnetic binary/ternary Zn_xCo_1−xFe₂O₄ (x = 0, 0.5, 1) nanoparticles were synthesized using a straightforward one-step microwave technique. To produce the Zn_xCo_1−xFe₂O₄ nanoparticles, iron [...] Read more.

In this study, magnetic binary/ternary Zn_xCo_1−xFe₂O₄ (x = 0, 0.5, 1) nanoparticles were synthesized using a straightforward one-step microwave technique. To produce the Zn_xCo_1−xFe₂O₄ nanoparticles, iron (III) nitrate nonahydrate, zinc nitrate hexahydrate, and cobalt nitrate hexahydrate were used as metal sources, with urea used as the fuel and ammonium nitrate as the oxidizer. These materials were combined in an alumina crucible covered by a CuO jacket to absorb microwave energy and facilitate calcination. The thermal treatment involved placing the alumina crucible in a domestic microwave oven at 450 W for 30 min. The key strengths of this experimental strategy include its simplicity, cost-effectiveness, and rapidity, aligning with green chemistry principles. The synthesized nanoparticles were characterized using X-ray diffraction (XRD), Fourier transform infrared (FT-IR) spectroscopy, a vibrating sample magnetometer (VSM), and Brunauer–Emmett–Teller (BET) analysis. XRD analysis confirmed the presence of the pure ferrite nanocrystalline phase. Scanning electron microscopy (SEM), employed with energy-dispersive X-ray spectroscopy (EDS), was used to study the surface morphology and analyze the elemental composition. The SEM analysis revealed that the synthesized magnetic nanoparticles had particle sizes ranging from 30 to 50 nm. Furthermore, we explored the potential use of these magnetic nanoparticles as photocatalysts for degrading organic pollutants such as methylene blue in aqueous solutions. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 355 KiB

Open AccessProceeding Paper

Synthesis of New 1Z,5Z-Dienoic Macrodiolides with Benzenyl and Naphthyl Moieties

by Ilgam Gaisin and Ilgiz Islamov

Chem. Proc. 2024, 16(1), 30; https://doi.org/10.3390/ecsoc-28-20111 - 12 Dec 2024

Viewed by 525

Abstract

Macrocycles represent an important class of compounds that are widespread in nature. Of particular interest to researchers are aromatic macrocyclic compounds, which, due to their rigid structure and unique physicochemical properties, can find application in many areas of science, industry and medicine. Previously, [...] Read more.

Macrocycles represent an important class of compounds that are widespread in nature. Of particular interest to researchers are aromatic macrocyclic compounds, which, due to their rigid structure and unique physicochemical properties, can find application in many areas of science, industry and medicine. Previously, we synthesized polyether aromatic macrodiolides, which showed intriguing antitumor properties. In the work, Peyrottes S. and co-authors showed that the introduction of biphenyl or naphthyl rings, as well as triple bonds, into the structure of the compounds they synthesized, not only helps to reduce the molecular flexibility of the molecule, but also increases the bioavailability after oral administration of the corresponding neutral prodrugs. Studies in mice have shown that the presence of two aromatic groups is well tolerated and has resulted in compounds with valuable properties in vitro and in vivo. Based on these results, in continuation of our research on the synthesis of biologically active macrodiolides, in the framework of this work, new aromatic macrocycles were synthesized, the structure of which, along with the 1Z,5Z-diene fragment, contains phenyl or naphthyl rings. The target polyester macrodiolides were obtained by Hf-catalyzed intermolecular cyclocondensation of 1,14-tetradeca-5Z,9Z-dienedioic acid with diols synthesized from dihydroxybenzenes and naphthalenediols. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1108 KiB

Open AccessProceeding Paper

Transamination of 3-[(Dimethylamino)methylidene]-5-arylfuran-2(3H)-thiones with the Participation of 1,2-Phenylenediamine

by Alexandra S. Tikhomolova and Alevtina Yu. Yegorova

Chem. Proc. 2024, 16(1), 31; https://doi.org/10.3390/ecsoc-28-20121 - 14 Nov 2024

Viewed by 215

Abstract

Synthesis of 3-[((2-aminophenyl)amino)methylidene]furan-2(3H)-thiones was carried out by transamination reaction of 5-arylfuran-2(3H)-thiones under the influence of 1,2-phenylenediamine. A probable scheme of their formation was proposed. Configurational features of the obtained compounds were established on the basis of IR and NMR [...] Read more.

Synthesis of 3-[((2-aminophenyl)amino)methylidene]furan-2(3H)-thiones was carried out by transamination reaction of 5-arylfuran-2(3H)-thiones under the influence of 1,2-phenylenediamine. A probable scheme of their formation was proposed. Configurational features of the obtained compounds were established on the basis of IR and NMR spectroscopy data, as well as using the NOESY 2D experiment. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 3640 KiB

Open AccessProceeding Paper

Theoretical Study of Intermolecular Interactions in Benzopyrans Substituted with Polyhaloalkyl Groups

by Lissette A. Haro-Saltos, Pablo M. Bonilla-Valladares and Christian D. Alcívar-León

Chem. Proc. 2024, 16(1), 32; https://doi.org/10.3390/ecsoc-28-20209 - 13 Dec 2024

Viewed by 554

Abstract

A study of the solid-state intermolecular interactions of twenty-nine benzopyrans substituted with polyhaloalkyl groups was carried out by quantum chemical calculations using the Mercury and WinGX computer programs. Molecular structures were obtained from crystallographic information files (CIF) of the CCDC database. C-H—O, C-H—X, [...] Read more.

A study of the solid-state intermolecular interactions of twenty-nine benzopyrans substituted with polyhaloalkyl groups was carried out by quantum chemical calculations using the Mercury and WinGX computer programs. Molecular structures were obtained from crystallographic information files (CIF) of the CCDC database. C-H—O, C-H—X, C-X—O and C-X—X type contacts, characterized as unconventional hydrogen bonds, were identified and calculated. The criteria used for distances and angles were d(D—A) < R(D) + R(A) + 0.50 and d(H—A) < R(H) + R(A)—0.12°, where D-H—A > 100.0°. D is the donor atom, A is the acceptor atom, R is the Van der Waals radius and d is the interatomic distance. In addition, Etter’s notation was used to describe sets of hydrogen bonds in organic crystals, detailing the intermolecular contacts and periodic arrangements of the crystal packing. It was corroborated that certain positions of halogen atoms and their interactions play an important role in stabilizing the crystal lattice. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 388 KiB

Open AccessProceeding Paper

New 1Z,5Z-Diene Compounds: Stereoselective Synthesis of Tetraenoic Macrodiolides

by Ilgiz Islamov and Ilgam Gaisin

Chem. Proc. 2024, 16(1), 33; https://doi.org/10.3390/ecsoc-28-20110 - 13 Dec 2024

Viewed by 560

Abstract

Macrocyclic compounds, including macrolactones and macrodiolides, play a significant role in the development of supramolecular chemistry, materials science, the perfume industry, and pharmaceuticals. In previous studies conducted by our group over several years, previously undescribed macrocyclic compounds containing pharmacophoric 1Z,5Z- diene fragments in [...] Read more.

Macrocyclic compounds, including macrolactones and macrodiolides, play a significant role in the development of supramolecular chemistry, materials science, the perfume industry, and pharmaceuticals. In previous studies conducted by our group over several years, previously undescribed macrocyclic compounds containing pharmacophoric 1Z,5Z- diene fragments in their structure were synthesized for the first time, which showed high potential in studies on cytotoxicity, apoptosis-inducing activity, effects on the cell cycle, and mitochondria in tumor cell lines (Jurkat, K562, U937). As part of the continuing research on the development of methods for synthesizing new unsaturated macrodiolides and studying their antitumor properties, this work presents, for the first time, the stereoselective synthesis of macrocyclic compounds based on 1,14 -tetradeca-5Z,9Z-dienoic acid and α,ω-alka-nZ, (n + 4)Z-dienediols (1,12-dodeca-4Z,8Z-dienediol, 1,14-tetradeca-5Z,9Z-dienediol, 1,16-octadeca-6Z,10Z-dienediol) in good yields. The method for the synthesis of new macrodiolides is based on the previously well-proven reaction of direct intermolecular cyclocondensation of dienedioic acid with diene diols in the presence of 5 mol.% hafnium(IV) triflate. As a result of the experiments, it was shown that the reaction between 1,14-tetradeca-5Z,9Z-dienedioic acid and 1,16-octadeca-6Z,10Z-dienediol in toluene proceeded within 18 h with the highest yield of 76%, with the formation of previously undescribed tetraenoic macrodiolides containing two 1Z,5Z-diene fragments in their structure. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 736 KiB

Open AccessProceeding Paper

The Effect of Curing Mode on the Parameters of Molecular Meshes of Epoxy and Polyester Copolymers

by Irina N. Vikhareva

Chem. Proc. 2024, 16(1), 34; https://doi.org/10.3390/ecsoc-28-20192 - 14 Nov 2024

Viewed by 238

Abstract

The establishment of the patterns of formation and structure of mesh polymers, as well as the methods of their controlled synthesis, makes it possible to rationally manage the technological processes of obtaining and processing materials based on them. This paper determines the possibility [...] Read more.

The establishment of the patterns of formation and structure of mesh polymers, as well as the methods of their controlled synthesis, makes it possible to rationally manage the technological processes of obtaining and processing materials based on them. This paper determines the possibility of directional variation in the parameters of the molecular grid of epoxy and polyester resin copolymers using a polyamide hardener. For this purpose, the influence of temperature regimes on the curing mixing technology of the original components was studied. The values of the Huggins constants were initially calculated. For this purpose, the swelling of copolymers in chloroform, xylene, dimethylformamide and acetone was studied. Taking into account the thermodynamic criteria, based on the results obtained, a solvent was selected that provides optimal swelling conditions for the synthesized copolymer. Experimental data describing the process of collecting copolymer samples were obtained. Using the Florey equation, the parameters of the structural grids of the developed polymer compositions were calculated. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 763 KiB

Open AccessProceeding Paper

Investigating SAR Insights into Royleanones for P-gp Modulation

by Gabrielle Bangay, Vera M. S. Isca, Florencia Z. Brauning, Jelena Dinic, Milica Pesic, Bernardo Brito Palma, Daniel J. V. A. dos Santos, Ana M. Díaz-Lanza, Eduardo Borges de Melo, João Paulo Ataide Martins and Patrícia Rijo

Chem. Proc. 2024, 16(1), 35; https://doi.org/10.3390/ecsoc-28-20158 - 12 Dec 2024

Viewed by 531

Abstract

Multidrug resistance (MDR) presents a significant challenge in modern pharmacotherapy, greatly diminishing the effectiveness of chemotherapeutic agents. A primary mechanism contributing to MDR is the overexpression of P-glycoprotein (P-gp), also known as MDR1, encoded by the ABCB1 gene, which hampers the success of [...] Read more.

Multidrug resistance (MDR) presents a significant challenge in modern pharmacotherapy, greatly diminishing the effectiveness of chemotherapeutic agents. A primary mechanism contributing to MDR is the overexpression of P-glycoprotein (P-gp), also known as MDR1, encoded by the ABCB1 gene, which hampers the success of cancer treatments. Plants from the Plectranthus genus (Lamiaceae) have been traditionally acknowledged for their diverse therapeutic applications. The principal diterpene from Plectranthus grandidentatus Gürke, 7α-acetoxy-6β-hydroxyroyleanone (Roy), has demonstrated anticancer properties against various cancer cell lines. Previously synthesized ester derivatives of Roy have shown improved binding affinity to P-gp. This study employs previously acquired in vitro data on the P-gp activity of Roy derivatives to develop a ligand-based pharmacophore model, highlighting critical features necessary for P-gp modulation. Utilizing these data, we predict the potential of five novel ester derivatives of Roy to modulate P-gp in vitro against resistant NCI-H460 cells. In silico structure–activity relationship (SAR) studies were conducted on 17 previously synthesized royleanone derivatives. A binary classification model was constructed, distinguishing inactive from active compounds, generating 11,016 molecular interaction field (MIF) descriptors from structures optimized at the DFT level. After variable reduction and selection, 12 descriptors were chosen, resulting in a model with two latent variables (LV), using only 34.14% of the encoded information for calibration (LV1: 26.82%; LV2: 7.32%). The activity prediction of new derivatives suggested that four of them have a high likelihood of activity, which will be validated in future in vitro biological assays. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 733 KiB

Open AccessProceeding Paper

Antioxidant and Anti-Inflammatory Activities of Ethanol Extract from Daucus crinitus Desf.

by Fellahi Manel, Dib Mohammed El Amine and Bensaid Okkacha

Chem. Proc. 2024, 16(1), 36; https://doi.org/10.3390/ecsoc-28-20164 - 14 Nov 2024

Viewed by 333

Abstract

Oxidative stress, a key factor in triggering inflammation, plays a central role in the development of various aging-related diseases, including cancer, Parkinson’s, and Alzheimer’s. In this context, plant phenolics represent a major group of bioactive compounds that act as primary antioxidants, effectively scavenging [...] Read more.

Oxidative stress, a key factor in triggering inflammation, plays a central role in the development of various aging-related diseases, including cancer, Parkinson’s, and Alzheimer’s. In this context, plant phenolics represent a major group of bioactive compounds that act as primary antioxidants, effectively scavenging free radicals and mitigating oxidative damage, thereby helping to counteract these pathological processes. The objective of this work was to examine the phytochemicals present in the ethanol extract of the aerial parts of Daucus crinitus Desf. and to evaluate their anti-inflammatory and antioxidant activities. Phytochemical screening of the ethanol extract revealed the presence of various chemical groups, including tannins, flavonoids, phenolic acids, and coumarins. The biological activity assessment demonstrated that the ethanol extract exhibited promising antioxidant and anti-inflammatory properties. Daucus crinitus may be a valuable source of bioactive molecules with potential antioxidant and anti-inflammatory benefits. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 5821 KiB

Open AccessProceeding Paper

Aryl Itaconic Acids from Aryl Aldehydes and (Triphenylphosphoranylidene)succinic Anhydride via a One-Pot Ring-Opening–Wittig Olefination–Hydrolysis Reaction

by Vijo Poulose, Salama Almheiri, Noura Alwahedi, Arwa Alzeyoudi, Maryam Aghaei, Sreeraj Gopi and Thies Thiemann

Chem. Proc. 2024, 16(1), 37; https://doi.org/10.3390/ecsoc-28-20117 - 14 Nov 2024

Viewed by 396

Abstract

(Triphenylphosphoranylidene)succinic anhydride, which is prepared from triphenylphosphine and maleic anhydride and is itself not reactive towards aryl aldehydes, is ring-opened with methanol to methyl (triphenylphosphoranylidene)succinate. In one pot, the newly formed phosphorane is reacted with aryl aldehydes to methyl aryl itaconates, which are [...] Read more.

(Triphenylphosphoranylidene)succinic anhydride, which is prepared from triphenylphosphine and maleic anhydride and is itself not reactive towards aryl aldehydes, is ring-opened with methanol to methyl (triphenylphosphoranylidene)succinate. In one pot, the newly formed phosphorane is reacted with aryl aldehydes to methyl aryl itaconates, which are subsequently hydrolyzed with aqueous sodium hydroxide to aryl itaconic acids. The biological activity of 12 aryl itaconic acids thus prepared against four gram-positive and four gram-negative bacterial strains has been studied. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1963 KiB

Open AccessProceeding Paper

Experimental and Theoretical Study of a New Functionalized Derivative of 3-Methyl-2-Trifluoromethyl Chromone

by Ariana Fiallos-Ayala, Christian David Alcívar-León, Pablo M. Bonilla-Valladares, Juan Carlos Romero-Benavides and Jorge Heredia-Moya

Chem. Proc. 2024, 16(1), 38; https://doi.org/10.3390/ecsoc-28-20116 - 14 Nov 2024

Viewed by 316

Abstract

The investigation of new chemical compounds with medicinal potential is essential for addressing a wide range of diseases and pathogens. Among these compounds, chromones and their functionalized derivatives stand out for their biological activity. In this study, a nitro-substituted derivative of 3-methyl-2-pentafluoroethylchromone was [...] Read more.

The investigation of new chemical compounds with medicinal potential is essential for addressing a wide range of diseases and pathogens. Among these compounds, chromones and their functionalized derivatives stand out for their biological activity. In this study, a nitro-substituted derivative of 3-methyl-2-pentafluoroethylchromone was synthesized through a nitration reaction with a 79% yield. The product was characterized using spectroscopic techniques such as vibrational (IR) and electronic (UV–Visible) spectroscopy, and ¹H and ¹³C nuclear magnetic resonance (NMR). Additionally, quantum chemical calculations at different theoretical levels were performed to complement the interpretation of the experimental results. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 748 KiB

Open AccessProceeding Paper

Development and Validation of the Stability of p-SCN-Bn-Df via the Reversed-Phase Chromatography Method: Practical Experiences

by Anjli Shrivastav, Mohd. Faheem, Vaibhav Pandey and Manish Dixit

Chem. Proc. 2024, 16(1), 39; https://doi.org/10.3390/ecsoc-28-20175 - 14 Nov 2024

Viewed by 292

Abstract

The DFO, a special hexadentate chelator with three hydroxamate moieties, is a bifunctional 1-(4-isothiocyanatophenyl)-3-[6,17-dihydroxy-7,10,18,21-tetraoxo-27-(N-acetylhydroxylamino)- 6,11,17, 22- tetraazaheptaeicosine] thiourea (p-SCN-Bn-Df), a significant next-generation ligand. The presence of the thiocyanate (-SCN) group makes it capable of hydrolysis and the protonation process. In this study aims [...] Read more.

The DFO, a special hexadentate chelator with three hydroxamate moieties, is a bifunctional 1-(4-isothiocyanatophenyl)-3-[6,17-dihydroxy-7,10,18,21-tetraoxo-27-(N-acetylhydroxylamino)- 6,11,17, 22- tetraazaheptaeicosine] thiourea (p-SCN-Bn-Df), a significant next-generation ligand. The presence of the thiocyanate (-SCN) group makes it capable of hydrolysis and the protonation process. In this study aims to optimize the HPLC protocol for 1-(4-isothiocyanatophenyl)-3-[6,17-dihydroxy-7,10,18,21-tetraoxo-27-(n-acetylhydroxylamino)-6,11,17,22-tetraazaheptaeicosine] thiourea (p-SCN-Bn-Df) via the Reversed-Phase Chromatography (RP-HPLC) method. A variety of mobile phases were tested in various ratios of solvent constituents such as methanol/water, acetonitrile/water, and phosphate buffer along with at variable pH concentrations. However, when employing a mobile phase consisting of water to acetonitrile containing 0.1% TFA (05:95, v/v) in an isocratic manner, satisfactory separation and symmetric peaks were observed. This method utilized an Eclipsed C-18 column (5 μm, 4.6 × 250 mm) column with a flow rate of 0.5 mL/min. The maximum absorption of p-SCN-Bn-Dfat 254 nm wavelength was selected as the detection wavelength. The Retention time (t_R) of p-SCN-Bn-Df was found at 5.205 min. The ICH guideline was used to evaluate the linearity, accuracy, precision, limit of detection (LOD), limit of quantitation (LOQ), specificity, and system appropriateness criteria to validate the optimized chromatographic and spectrophotometric procedures. For accurate compound separation in pharmaceutical and environmental analyses, this phase is adaptable and often used. This study is useful for the evaluation of p-SCN-Bn-Df QC parameters and chelation rates with different radioisotopes e.g., Zirconuim-89 (Zr-89). Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 1549 KiB

Open AccessProceeding Paper

Interaction of Biomolecules with Silver Nanoparticles Prepared via Intramolecular Redox Reaction of Ag(I) Complexes as Their Precursors

by Iveta S. Turomsha, Natalia V. Loginova, Maxim Y. Gvozdev, Tatiana V. Koval’chuk-Rabchinskaya and Nikolai P. Osipovich

Chem. Proc. 2024, 16(1), 40; https://doi.org/10.3390/ecsoc-28-20173 - 14 Nov 2024

Viewed by 343

Abstract

Nanoparticles are known to have a high specific surface area, which accounts for an increased probability of their interaction with bacterial cells. Therefore, the application of silver(I) nanoparticles (AgNPs) and their nanocomposites as antimicrobial agents against drug-resistant bacterial strains appears to be prospective. [...] Read more.

Nanoparticles are known to have a high specific surface area, which accounts for an increased probability of their interaction with bacterial cells. Therefore, the application of silver(I) nanoparticles (AgNPs) and their nanocomposites as antimicrobial agents against drug-resistant bacterial strains appears to be prospective. A critical point for the advancement of AgNPs into clinical practice is a fundamental understanding of their behavior in biological systems, including protein binding and interaction with blood components, which reflects their toxicity. The latter is primarily determined by the physicochemical properties of AgNPs, namely their size, shape, surface chemistry, etc. Therefore, nanotoxicity may be substantially reduced through the manipulation of certain physicochemical characteristics of AgNPs, increasing their biocompatibility and hence paving the way for possible biomedical applications. In this study we have focused on estimating the binding affinity of the synthesized Ag(I) complexes of 2-(4,6-di-tert-butyl-2,3-dihydroxyphenylsulfanyl)-acetic acid and 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde isonicotinoyl hydrazone, as well as AgNPs derived thereof to bovine serum albumin (BSA) and hemoglobin by the fluorimetric method. Furthermore, cellular toxicity of the AgNPs towards human erythrocytes was measured in a hemolysis assay. Organosols formed by the Ag(I) complexes upon their reduction to AgNPs in acetonitrile and DMSO were characterized by the transmission electron microscopy (TEM) method and atomic force microscopy (AFM). Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 714 KiB

Open AccessProceeding Paper

A Straightforward and Efficient Approach to the Synthesis of 3-Cyano-Coumarine Derivatives

by Asmaa Kebaili, Fatima Belhadj, Zahira Kibou, Julio A. Seijas, M. Pilar Vazquez Tato and Noureddine Choukchou-Braham

Chem. Proc. 2024, 16(1), 41; https://doi.org/10.3390/ecsoc-28-20113 - 14 Nov 2024

Viewed by 322

Abstract

Oxygen heterocycles represent a significant category of organic molecules that are abundant in nature and important in scientific research due to their use in diverse applications across various fields. Coumarins, in particular, comprise a wide range of compounds known for their extensive biological [...] Read more.

Oxygen heterocycles represent a significant category of organic molecules that are abundant in nature and important in scientific research due to their use in diverse applications across various fields. Coumarins, in particular, comprise a wide range of compounds known for their extensive biological activities, making them invaluable in medicine, pharmacology, cosmetics, and the food industry. The biological effects and potential applications of coumarins are closely tied to their specific chemical structures. As a result, researchers frequently engage in the synthesis of coumarin derivatives to explore their varied uses. In this context, we focused on the synthesis of 3-cyano-coumarin and its derivatives. This study introduces a simple synthesis method that enables the efficient and accessible production of these structures under mild, environmentally friendly conditions, yielding excellent results. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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14 pages, 6163 KiB

Open AccessProceeding Paper

Phytochemical Constituents from Globimetula oreophila as Plasmepsin I and II Inhibitors in Antimalarial Drug Discovery: An In Silico Approach

by Dauda Garba, Bila Hassan Ali, Bashar Bawa, Abdullahi Maryam, Hamza Asmau Nasiru, Yahaya Mohammed Sani, Muhammad Garba Magaji, Musa Isma’il Abdullahi, Aliyu Muhammad Musa and Hassan Halimatu Sadiya

Chem. Proc. 2024, 16(1), 42; https://doi.org/10.3390/ecsoc-28-20220 - 14 Nov 2024

Viewed by 280

Abstract

Malaria remains a critical global health challenge, particularly affecting Sub-Saharan Africa. Plasmepsins, vital in hydrolyzing peptide bonds within proteins, present promising targets for antimalarial drugs. Plasmepsins I and II, key aspartic proteases, are crucial in various parasite processes. This study investigates the inhibitory [...] Read more.

Malaria remains a critical global health challenge, particularly affecting Sub-Saharan Africa. Plasmepsins, vital in hydrolyzing peptide bonds within proteins, present promising targets for antimalarial drugs. Plasmepsins I and II, key aspartic proteases, are crucial in various parasite processes. This study investigates the inhibitory properties of quercetin, quercetrin, dihydrostilbene, 4′-methoxy-isoliquiritigenin, and stigmasterol from Globimetula oreophila on plasmepsins through in silico techniques, including ADME predictions and molecular docking. Results reveal strong interactions of these compounds with active site residues, with quercetrin and stigmasterol displaying notable binding affinities. These findings suggest the potential of G. oreophila metabolites as potent plasmepsin inhibitors, offering prospects for malaria treatment and prevention. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1595 KiB

Open AccessProceeding Paper

Synthesis of Triazolyl Derivatives Based on Thiazolo[3,2-a]pyrimidine Propargyl Ethers

by Elina Gabitova, Artem Agarkov, Mariya Mailyan, Anna Nefedova, Alexander Ovsyannikov, Lubov Frantsuzova, Olga Lodochnikova, Svetlana Solovieva and Igor Antipin

Chem. Proc. 2024, 16(1), 43; https://doi.org/10.3390/ecsoc-28-20126 - 14 Nov 2024

Viewed by 316

Abstract

This work is devoted to the synthesis of triazolyl derivatives based on propargyl ethers of the thiazolo[3,2-a]pyrimidine series by [3+2]-cycloaddition and the study of their structure in solution and crystalline phase. The formation of homochiral chains in the crystalline phase is [...] Read more.

This work is devoted to the synthesis of triazolyl derivatives based on propargyl ethers of the thiazolo[3,2-a]pyrimidine series by [3+2]-cycloaddition and the study of their structure in solution and crystalline phase. The formation of homochiral chains in the crystalline phase is attributed to the establishment of a halogen bond between the bromine atom and the nitrogen atom of the nitrile group. Additionally, the generation of a racemic dimer is linked to the formation of a halogen bond between the bromine atom and the nitrogen atom of the triazolyl fragment. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 361 KiB

Open AccessProceeding Paper

Synthesis of Novel Aryl-Substituted Acetylenic Monoterpene Analogues by Sonogashira Coupling

by Rinat Gubaidullin and Lyudmila Parfenova

Chem. Proc. 2024, 16(1), 44; https://doi.org/10.3390/ecsoc-28-20124 - 14 Nov 2024

Viewed by 243

Abstract

The synthesis of new aryl-substituted acetylenic monoterpene derivatives was carried out by the Sonogashira reaction. The reactions proceed in the presence of PdCl₂(PPh₃)₂, CuI and Et₃N and provide aryl-substituted acetylenic monoterpenes with an isolated yield of 70–82%. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 726 KiB

Open AccessProceeding Paper

Synthesis of Novel Benzocaine and Procaine Glycodrugs

by Natividad Bejarano Rengel, Juliana Esteche, Cintia C. Santiago and Agustín Ponzinibbio

Chem. Proc. 2024, 16(1), 45; https://doi.org/10.3390/ecsoc-28-20119 - 14 Nov 2024

Viewed by 434

Abstract

In this manuscript, we present the synthesis and structural identification of two novel glycodrugs derived from benzocaine and procaine. D-galactose was converted into a substrate suitable for the introduction of amino derivatives at the C6 position. The glycodrugs were obtained in good yields [...] Read more.

In this manuscript, we present the synthesis and structural identification of two novel glycodrugs derived from benzocaine and procaine. D-galactose was converted into a substrate suitable for the introduction of amino derivatives at the C6 position. The glycodrugs were obtained in good yields through a two-step process involving the formation of an imine followed by subsequent reduction. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 613 KiB

Open AccessProceeding Paper

In Silico Evaluation of the Potential for the Rational Use of Garlic and Onion Crop Residue Extracts in Cosmetics

by Milena Ivkovic, Milan Ilic, Natasa Nastic, Sladjana Krivosija, Senka Vidovic and Mire Zloh

Chem. Proc. 2024, 16(1), 46; https://doi.org/10.3390/ecsoc-28-20217 - 14 Nov 2024

Viewed by 326

Abstract

Crop residue after harvesting onion (Allium cepa) and garlic (Allium sativum) has great potential in the development of value-added products due to the presence of a range of bioactive compounds. The potential of compounds identified in crop residue extracts [...] Read more.

Crop residue after harvesting onion (Allium cepa) and garlic (Allium sativum) has great potential in the development of value-added products due to the presence of a range of bioactive compounds. The potential of compounds identified in crop residue extracts to be used in cosmetics was evaluated in silico, including prediction of their interactions with selected skin target proteins (SIRT1, TGF-β, and elastase). Molecular docking results obtained using AutoDock Vina revealed that stronger binding affinity was observed between TGF-β protein and small molecules such as rutin and procyanidin A2 compared to elastase. On the other side, SIRT1 protein showed the best interaction with quercetin and kaempferol. Potential side effects on the skin of individual molecules in extracts of garlic and onion were predicted using regulated databases for skin sensitization tests (Ambit, SkinSensDB, Danish QSAR Database, and Skin Doctor CP). These in silico predictions have shown that the most active molecules are not irritating or corrosive to the skin. The obtained results indicate significant potential for the use of crop residue extracts in the development of skincare products from sustainable resources while addressing the issues of waste. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 6437 KiB

Open AccessProceeding Paper

Studies on Anti-Cancer Agents from Natural Resources with Special Reference to Cannabis sativa and Datura metel L.

by Shrimanti Chakraborty, Piyush Kumar and Manik Ghosh

Chem. Proc. 2024, 16(1), 47; https://doi.org/10.3390/ecsoc-28-20216 - 14 Nov 2024

Viewed by 315

Abstract

Cancer remains a significant challenge, prompting the exploration of new therapies. Breast cancer is the most prevalent among women, and current medications often have serious side effects. Additionally, there is limited research on natural resources that have historically provided bioactive compounds with potential [...] Read more.

Cancer remains a significant challenge, prompting the exploration of new therapies. Breast cancer is the most prevalent among women, and current medications often have serious side effects. Additionally, there is limited research on natural resources that have historically provided bioactive compounds with potential anti-cancer properties. This study examines two such resources—Cannabis sativa and Datura metel L.—both known for their pharmacological diversity and traditional medicinal use. Cannabis sativa, with its major constituents Δ9-tetrahydrocannabinol (THC) and cannabidiol (CBD), has garnered considerable interest. Datura metel L., despite its toxicity, contains alkaloids like scopolamine and withametelin, which have shown cytotoxic properties against cancer cells. This study selected five breast cancer-related receptors, docking them against various phytoconstituents in both plants to identify potent cytotoxic entities. Target proteins were extracted from the PDB database, and docking studies were performed using AutoDock software. The docking scores of the phytochemicals were then compared with one another. The docking studies on Cannabis sativa revealed that apigenin (−8.15), β-caryophyllene oxide (−8.35), THCA (−8.84), epicatechin (−8.18), and vitexin (−9.58) showed good interaction with the PARP receptor (PDB ID: 5DS3), while cannabidiol (−8.38) and cannabichromene (−8.36) showed strong interactions with CDK4/6 (PDB ID: 6GS7). Additionally, strychnine (−9.99), naringin (−9.19), and luteolin (−8) demonstrated good interactions with the estrogen receptor (PDB ID: 3ERT). In the case of Datura metel L., withametelin (−10.69) and dinoxin B (−10.72) showed good interactions with the estrogen receptor (PDB ID: 3ERT), and scopolamine (−8.24) with CDK4/6 (PDB ID: 6GS7). These findings suggest that these phytoconstituents possess anti-cancer activities. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1592 KiB

Open AccessProceeding Paper

Straightforward Synthesis of BHQ-3 Amine: An Azo Dark-Quencher for FRET-Based Protease Activity Assays

by Cátia D. F. Martins, Maria Manuela M. Raposo and Susana P. G. Costa

Chem. Proc. 2024, 16(1), 48; https://doi.org/10.3390/ecsoc-28-20170 - 14 Nov 2024

Viewed by 357

Abstract

A Black Hole Quencher-3 (BHQ-3) derivative was synthesized through an azo-coupling reaction between Methylene Violet 3RAX and a tertiary aniline functionalized with a pendant primary amine, allowing subsequent peptide conjugation. The synthesized compounds were characterized using NMR, UV–vis absorption, fluorescence spectroscopy, and mass [...] Read more.

A Black Hole Quencher-3 (BHQ-3) derivative was synthesized through an azo-coupling reaction between Methylene Violet 3RAX and a tertiary aniline functionalized with a pendant primary amine, allowing subsequent peptide conjugation. The synthesized compounds were characterized using NMR, UV–vis absorption, fluorescence spectroscopy, and mass spectrometry. The spectral properties of a Cy5/BHQ-3 amine pair were investigated through titration experiments in PBS (pH 7.4). The results confirmed Förster Resonance Energy Transfer (FRET), along with additional dynamic quenching, as evidenced by the Stern–Volmer analysis. The Stern–Volmer constant (K_SV) was determined to be 1.40 × 10⁵ M⁻¹. These findings confirm the potential of this system for use in molecular probes and bioimaging applications. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 541 KiB

Open AccessProceeding Paper

Synthesis, Spectral Studies and Antimicrobial Activity of 2-Aryl-3-(2′-n-butyl-4′-chloro-1′-H,5′-imidazolyl)-quinoxazolines

by Asha K. Joshi and Dipak M. Purohit

Chem. Proc. 2024, 16(1), 49; https://doi.org/10.3390/ecsoc-28-20100 - 14 Nov 2024

Viewed by 306

Abstract

Quinoxazoline derivatives are renowned for their extensive pharmacological activities and substantial industrial importance. Recognizing their multifaceted applications, this study aims to synthesize novel quinoxazoline derivatives, specifically Arylimidazolyl quinoxazolines, and investigate their antimicrobial properties. The synthesis process involved the condensation of a precursor molecule [...] Read more.

Quinoxazoline derivatives are renowned for their extensive pharmacological activities and substantial industrial importance. Recognizing their multifaceted applications, this study aims to synthesize novel quinoxazoline derivatives, specifically Arylimidazolyl quinoxazolines, and investigate their antimicrobial properties. The synthesis process involved the condensation of a precursor molecule (1a-1j) with bromine (Br₂) in acetic acid (HAc) and 1,2-diaminobenzene, culminating in the efficient synthesis of the targeted quinoxazoline framework (2a-2j). The structural elucidation of the compounds was accomplished through employing a synergistic approach of spectroscopic techniques, notably NMR, IR spectroscopy, and mass, which confirmed the successful formation of targeted molecules. The antimicrobial efficacy of these new derivatives was evaluated through a series of bioassays against a diverse panel of bacterial and fungal strains. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 1921 KiB

Open AccessProceeding Paper

Microwave Synthesis and Antimicrobial Evaluation of Selected Aminophosphonates

by Nour El Houda Felkaoui, Abdelkader Hellal, Khadidja Fadli and Yousra Miloudi

Chem. Proc. 2024, 16(1), 50; https://doi.org/10.3390/ecsoc-28-20244 - 23 Dec 2024

Viewed by 407

Abstract

In the search for new bioactive molecules, a series of new molecules from the phosphonate family were synthesized via the Kabachnik–Fields reaction (phosphonate ester) and the Irani–Moedritzer reaction (phosphonic acids). Their structures were characterized by various spectroscopic methods, including IR and UV-vis. The [...] Read more.

In the search for new bioactive molecules, a series of new molecules from the phosphonate family were synthesized via the Kabachnik–Fields reaction (phosphonate ester) and the Irani–Moedritzer reaction (phosphonic acids). Their structures were characterized by various spectroscopic methods, including IR and UV-vis. The synthesized compounds were screened for in vitro antimicrobial activity against Gram-positive (Bacillus subtilis and Staphylococcus aureus) and Gram-negative (Escherichia coli and Pseudomonas aeruginosa) bacteria, using the well method. The results also showed that all the products synthesized exhibited good activity with a zone of inhibition: D > 8, except one product against S. aureus bacteria. The three products were tested for their antifungal effects against three pathogenic fungal strains, namely Candida albicans, Aspergillus niger, and Penicillium notatum. The results show that the zones of maximum inhibition were observed against P. notatum (35.5 mm). Therefore, the biological tests showed that all the compounds studied exhibited high antibacterial and antifungal activities. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 990 KiB

Open AccessProceeding Paper

Synthesis and Evaluation of Novel 5-Arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) Thiazolidin-4-Ones as Anti-Microbial Agents

by Pritam N. Dube and Yogita B. Thombare

Chem. Proc. 2024, 16(1), 51; https://doi.org/10.3390/ecsoc-28-20120 - 14 Nov 2024

Viewed by 249

Abstract

The development of combination chemotherapeutic drugs, each with distinct mechanisms and minimal side effects, is crucial in combating antimicrobial resistance. Discovering novel drugs with diverse mechanisms is laborious and time-consuming. Alternatively, combining multiple pharmacophores into a single molecule offers a promising strategy to [...] Read more.

The development of combination chemotherapeutic drugs, each with distinct mechanisms and minimal side effects, is crucial in combating antimicrobial resistance. Discovering novel drugs with diverse mechanisms is laborious and time-consuming. Alternatively, combining multiple pharmacophores into a single molecule offers a promising strategy to develop more effective treatments. In this study, we synthesized and assessed the antimicrobial activity of novel 5-arylidene-2-(7-chloroquinolin-6-yl)-3-(pyrimidin-2-yl) thiazolidin-4-ones. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 4584 KiB

Open AccessProceeding Paper

Kinetic and Equilibrium Analysis of Tartrazine Photocatalytic Degradation Using Iron-Doped Biochar from Theobroma cacao L. Husk via Microwave-Assisted Pyrolysis

by Jean Espinoza, Elvia V. Cabrera, Ullrich Stahl and Jhonny Correa-Abril

Chem. Proc. 2024, 16(1), 52; https://doi.org/10.3390/ecsoc-28-20265 - 14 Nov 2024

Viewed by 424

Abstract

The MAP process involved placing acid-pretreated biomass (CPH) in a domestic microwave oven at 600 W for 15 min. This was followed by a doping process with iron salts (+2, +3) to obtain BCCPH-Fe. Characterization of BCCPH-Fe was carried out using surface analysis [...] Read more.

The MAP process involved placing acid-pretreated biomass (CPH) in a domestic microwave oven at 600 W for 15 min. This was followed by a doping process with iron salts (+2, +3) to obtain BCCPH-Fe. Characterization of BCCPH-Fe was carried out using surface analysis (BET), TGA analysis and FTIR. Subsequently, the photodegradation process was performed using three different light sources (solar, UV 254 nm and UV 356 nm), with tartrazine as the adsorbate. The effect of pH on photodegradation was studied, and the percentage of degradation was evaluated through equilibrium and kinetic studies. The amount of BCCPH-Fe, tartrazine concentration, and exposure time to the light source were also evaluated. The best conditions for the photodegradation process were: light source was 254 nm, pH of 5, 1 g of BCCPH-Fe over 100 mL of tartrazine, 25 ppm tartrazine concentration, and 40 h exposure time. Under these conditions, a 93.45% removal of tartrazine was achieved. The experimental data of the adsorption equilibrium best fit the Langmuir-Hinshelwood model, while the adsorption kinetics best fit the pseudo-first-order model. The apparent kinetic constant was 0.04053 [h⁻¹], and the correlation coefficient was 0.98667. In conclusion, photodegradation using BCCPH-Fe can be an effective method for the removal of tartrazine from wastewater, offering a sustainable alternative to traditional methods. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1251 KiB

Open AccessProceeding Paper

Amine Oxide: Synthesis and Analysis

by Mikhail Aleksandrovich Silin, Lyubov Abdulaevna Magadova, Polina Konstantinovna Krisanova, Mikhail Mikhailovich Muhin, Sergei Alekseevich Borodin, Andrey Alekseevich Filatov and Savely Alekseevich Mityurev

Chem. Proc. 2024, 16(1), 53; https://doi.org/10.3390/ecsoc-28-20114 - 14 Nov 2024

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Abstract

This paper presents the laboratory synthesis of zwitterionic surfactant—oleylamido propyldimethylamine oxide (OADAO), as well as the selection of conditions for its implementation. The results of the analysis of synthesis products by potentiometric titration and IR-Fourier spectroscopy methods are presented, which prove the presence [...] Read more.

This paper presents the laboratory synthesis of zwitterionic surfactant—oleylamido propyldimethylamine oxide (OADAO), as well as the selection of conditions for its implementation. The results of the analysis of synthesis products by potentiometric titration and IR-Fourier spectroscopy methods are presented, which prove the presence of the target product in the composition of the reaction mass at the end of synthesis. The positive results of the synthesis and the absence of light organochlorine compounds (LOC) in the end products allow us to further consider OADAO, for example, as a gelling agent for aqueous fracturing fluids, by studying its technological characteristics. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1214 KiB

Open AccessProceeding Paper

Computational Investigations of Arylnaphthalene Lignan Lactones as Anticancer Agents

by Rachida Mansouri, Abdeslem Bouzina and Yousra Ouafa Bouone

Chem. Proc. 2024, 16(1), 54; https://doi.org/10.3390/ecsoc-28-20218 - 14 Nov 2024

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Abstract

Cancer is a significant global health challenge, comprising over 200 distinct types that severely impact life expectancy and account for high mortality rates in the 21st century. This complexity underscores the urgent need for ongoing research, preventive strategies, and improved treatment options. In [...] Read more.

Cancer is a significant global health challenge, comprising over 200 distinct types that severely impact life expectancy and account for high mortality rates in the 21st century. This complexity underscores the urgent need for ongoing research, preventive strategies, and improved treatment options. In the quest for new anticancer drug candidates, arylnaphthalene lignan lactones—natural compounds found in plants like Phyllanthus and Cleistanthus—have gained attention due to their antioxidant, anti-inflammatory, and anticancer properties. An in silico study was conducted to evaluate their potential against colon cancer by targeting epidermal growth factor receptor (EGFR), a key tyrosine kinase. Docking simulations revealed that these compounds exhibited excellent stability within the active site of EGFR, with docking scores of −8.02 and −7.96 kcal/mol. Further, the derivatives demonstrated significant interactions, including hydrogen bonds with Met 769 and hydrophobic contacts within the EGFR cavity, akin to those formed by the known inhibitor 4-anilinoquinazoline. An ADMET analysis was also performed to evaluate their pharmacokinetic properties and toxicity, further supporting their potential as promising anticancer agents. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 607 KiB

Open AccessProceeding Paper

In Silico Pharmacological Prediction of Capitavine, Buchenavianine and Related Flavonoid Alkaloids

by Renata Gašparová and Natália Kabaňová

Chem. Proc. 2024, 16(1), 55; https://doi.org/10.3390/ecsoc-28-20222 - 14 Nov 2024

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Abstract

Flavonoid alkaloids represent an interesting subgroup of the alkaloid family. Several plants containing flavonoid alkaloids are used in folk medicine for the treatment of various diseases. The interesting biological properties of flavonoid alkaloids make them attractive candidates for lead compounds in drug discovery. [...] Read more.

Flavonoid alkaloids represent an interesting subgroup of the alkaloid family. Several plants containing flavonoid alkaloids are used in folk medicine for the treatment of various diseases. The interesting biological properties of flavonoid alkaloids make them attractive candidates for lead compounds in drug discovery. Capitavine, or 5,7-dihydroxy-6-(1-methylpiperidin-2-yl)flavone, and related compounds, belong to piperidine–flavonoid alkaloids, possessing a piperidine ring connected to the C6-position of flavonoid skeleton, while buchenavianine is C8 piperidine-bonded analog. Capitavine derivatives were isolated mainly from Buchenavia capitata, while buchenavianine derivatives are present mainly in B. macrophylla. It was found that the chloroform extract of the leaves of B. capitata showed anti-HIV activity. The biological activity of capitavine and buchenavianine derivatives needs to be investigated in terms of their pharmacokinetic properties and toxicity, which are important factors in finding potential drug candidates. The present in silico study using SwissADME, Osiris, and Molinspiration software shows that studied capitavine-derived flavonoid alkaloids exhibit considerable bioactivity for the GPCR ligand (0.12 to 0.20), as enzyme inhibitors (0.17 to 0.22) and as nuclear receptor ligands (0.07 to 0.28). All compounds exhibit good gastrointestinal absorption and low risks of being irritants, tumorigenic, or having a reproductive effect. The risk of mutagenicity was calculated for two compounds related to buchenavianine, and at this point the role of 5-methoxy group appears to be crucial for the low risk of mutagenicity. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1213 KiB

Open AccessProceeding Paper

Molecular Docking/ADME-TOX-Based Analysis for New Anti-Colorectal Cancer Through Peroxiredoxin 1 Inhibition

by Imane Bensahbane, Nadjib Melkemi, Ismail Daoud and Faiza Asli

Chem. Proc. 2024, 16(1), 56; https://doi.org/10.3390/ecsoc-28-20215 - 14 Nov 2024

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Abstract

Colorectal cancer ranks as the third most prevalent form of cancer on a global scale. The abnormal expression of Peroxiredoxin 1, or PRDX1, plays an important role in cancer progression and tumor cell survival. This makes inhibiting this protein a promising target for [...] Read more.

Colorectal cancer ranks as the third most prevalent form of cancer on a global scale. The abnormal expression of Peroxiredoxin 1, or PRDX1, plays an important role in cancer progression and tumor cell survival. This makes inhibiting this protein a promising target for colorectal cancer treatment. In order to develop effective PRDX1 inhibitors, a drug design investigation based on computational methods was carried out using a collection of recently synthesized compounds derived from two main chemical base structures: C-5 sulfenylated amino uracils and 1,2,3-triazole benzothiazole derivatives. To obtain the PRDX1 protein PDB ID: 7WET, molecular docking was performed on the studied compounds in combination with PRDX1. The 1,2,3-triazole benzothiazole derivatives showed interesting docking results. For instance, nine promising candidates were distinguished by their formation of better stable complexes with PRDX1 in terms of E (binding) from −7.0 to −7.3 kcal/mol, namely, 7WET-L18, 7WET-L17, 7WET-L25, 7WET-L19, 7WET-L20, 7WET-L26, 7WET-L22, 7WET-L23, and 7WET-L24, as well as an E of −6.8 kcal/mol for Celastrol, a known PRDX1 inhibitor. Moreover, an extensive evaluation of ADME-TOX was performed to predict the pharmacokinetic, pharmacodynamic, and toxicological properties of the compounds studied. The findings offer significant support for the prospective application of these analogs in the fight against colorectal cancer. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 836 KiB

Open AccessProceeding Paper

In Silico Evaluation of Novel 2-Pyrazoline Carboxamide Derivatives as Potential Protease Inhibitors Against Plasmodium Parasites

by Yusuf Jimoh, Idris Yunusa Abdullah, Asmau Nasir Hamza, Maryam Abdullahi, Jibril Ahmadu, Lukman Ali Hassan, Muhammad Shamsudeen Yakubu and Zukhruf Salami

Chem. Proc. 2024, 16(1), 57; https://doi.org/10.3390/ecsoc-28-20224 - 14 Nov 2024

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Abstract

Malaria, a devastating disease caused by Plasmodium parasites, continues to pose a significant threat to global health, with increasing resistance to current antimalarial drugs. In this study, we employed an in silico approach to design and evaluate novel 2-pyrazoline carboxamide derivatives as potential [...] Read more.

Malaria, a devastating disease caused by Plasmodium parasites, continues to pose a significant threat to global health, with increasing resistance to current antimalarial drugs. In this study, we employed an in silico approach to design and evaluate novel 2-pyrazoline carboxamide derivatives as potential protease inhibitors against Plasmodium falciparum. Our results show that all the designed ligands exhibit good drug-like properties, satisfying Lipinski’s rule of five, and have low toxicity profiles. Molecular docking studies revealed that five newly designed ligands (P5, P6, P7, P11, and P13) exhibit promising binding affinities and interactions with key protease enzymes involved in the hemoglobin degradation pathway, including Falcipain-2, Falcipain-3, and Plasmepsin-2 with PDB (Protein Data Bank) codes of 6JW9, 3BWK, and 1LF3, respectively. Notably, ligand P13 showed the strongest binding affinity with Falcipain-2, forming an additional hydrogen bond with CYS42, an essential residue for the enzyme’s catalytic activity. The interactions between the ligands and the enzymes suggest a competitive inhibition mechanism, with the potential to disrupt the hemoglobin degradation pathway and halt the parasite’s lifecycle. The biological implications of these findings are significant, as they suggest that these novel ligands could be effective against Plasmodium parasites, particularly in the context of increasing resistance to current antimalarial drugs. Overall, this study provides valuable insights into the potential of novel 2-pyrazoline carboxamide derivatives to serve as protease inhibitors against Plasmodium parasites, highlights their potential as a promising strategy for antimalarial drug development, and demonstrates the importance of in silico approaches in the discovery of novel therapeutics. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

5 pages, 1317 KiB

Open AccessProceeding Paper

Queen Bee Acid 10H2DA Halts HCT-116 Cells’ Collective Migration via Elevation of E-Cadherin and β-Catenin

by Milena M. Jovanović, Dejan Arsenijević, Dalibor Nikolić, Igor Saveljić and Dragana Šeklić

Chem. Proc. 2024, 16(1), 58; https://doi.org/10.3390/ecsoc-28-20180 - 14 Nov 2024

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Abstract

A particular interest in oncology has presented the migration of cancer cells, collective and individual, and the switch between these two types of motilities greatly complicates this disease and adds further complexity to therapeutic approaches. Intercellular connections play a prominent role in motility, [...] Read more.

A particular interest in oncology has presented the migration of cancer cells, collective and individual, and the switch between these two types of motilities greatly complicates this disease and adds further complexity to therapeutic approaches. Intercellular connections play a prominent role in motility, especially E-cadherin and β-catenin markers. Unsaturated fatty acid 10HDA has not been investigated so far on the collective migration of colorectal carcinoma (CRC) cells and components of intercellular junctions. Our study highlights the prominent anti-migratory effects of 10H2DA on HCT-116 cells, obviously due to the significant increase in E-cadherin and β-catenin protein expression, which are crucial targets in cancer treatment, and therefore should be extensively analyzed. In conclusion, 10H2DA presents a valuable source of anticancer potential worthy of further investigation regarding the development of therapeutic strategies against CRC. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 300 KiB

Open AccessProceeding Paper

A Phytochemical, Antioxidant, and Anti-Inflammatory Study of Extracts of the Apiaceae Family and Their Fractions: “Study of the Effect of Synergy and/or Antagonism”

by Fatima Zohra Belbachir, Lamia Hamdan and Kamel Mustapha Dali Yahia

Chem. Proc. 2024, 16(1), 59; https://doi.org/10.3390/ecsoc-28-20163 - 14 Nov 2024

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Abstract

The aim of this work was to study the phytochemical screening, anti-inflammatory activity, and antioxidant activity of extracts of a Saharan plant in the Apiaceae family. Qualitative phytochemical analysis of the MeOH extract showed that it is mainly composed of flavonoids. The result [...] Read more.

The aim of this work was to study the phytochemical screening, anti-inflammatory activity, and antioxidant activity of extracts of a Saharan plant in the Apiaceae family. Qualitative phytochemical analysis of the MeOH extract showed that it is mainly composed of flavonoids. The result of the evaluation of antioxidant activity revealed that the polar fractions of the MeOH extract have very powerful antioxidant activity, characterized by inhibitory concentrations of 50% of the DPPH free radical (IC50 = 0.084 mg/mL), better than that of BHT (IC50 = 0.69 mg/mL). They also showed higher anti-inflammatory activity than that of diclofenac (IC50 = 35.5 μg/mL). In fact, these new results could lead to powerful approaches for the development of new antioxidant compounds. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1904 KiB

Open AccessProceeding Paper

Molecular Mobility of Different Forms of Ketoprofen Based on DFT Calculation Data

by Kapitolina A. Logacheva, Alexander V. Belushkin, Polina A. Gergelezhiu, Alexander B. Eresko, Sergey N. Malakhov, Elena V. Raksha, Ludmila I. Savostina and Dorota M. Chudoba

Chem. Proc. 2024, 16(1), 60; https://doi.org/10.3390/ecsoc-28-20162 - 14 Nov 2024

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Abstract

Ketoprofen is a representative of the group of non-steroidal anti-inflammatory drugs widely used in modern medical therapy. The intramolecular dynamics of ketoprofen are of particular importance, since the mobility of its main structural fragments is one of the key factors determining the efficiency [...] Read more.

Ketoprofen is a representative of the group of non-steroidal anti-inflammatory drugs widely used in modern medical therapy. The intramolecular dynamics of ketoprofen are of particular importance, since the mobility of its main structural fragments is one of the key factors determining the efficiency of drug binding to the enzyme. Investigations of such processes taking into account the acid–base properties of ketoprofen have not been carried out. DFT calculations for molecular, anionic and ion pair forms of ketoprofen were performed at the BP86/def2-TZVP level of theory using ORCA software. The intramolecular dynamics of the main structural fragments were investigated for the molecular, anionic and ion pair forms of ketoprofen. The most stable conformers were revealed for all considered forms, and the barriers of intramolecular rotation were estimated. It was shown that the structures of the ketoprofen forms studied are labile but characterized by different mobility. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 993 KiB

Open AccessProceeding Paper

Silica-Polymer Ionogel for Energy Storage Applications

by Raquel San Emeterio, Antía Santiago-Alonso, Pablo Vallet, María Villanueva, Josefa Salgado and Juan José Parajó

Chem. Proc. 2024, 16(1), 61; https://doi.org/10.3390/ecsoc-28-20199 - 14 Nov 2024

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Abstract

Ionic Liquids (ILs) are composed of ions, usually an organic cation with an organic or inorganic anion, with a melting point below 100 °C and in most cases below room temperature. These compounds exhibit important and characteristic properties such as high ionic conductivity, [...] Read more.

Ionic Liquids (ILs) are composed of ions, usually an organic cation with an organic or inorganic anion, with a melting point below 100 °C and in most cases below room temperature. These compounds exhibit important and characteristic properties such as high ionic conductivity, good thermal and electrochemical stability and low toxicity and flammability. Subsequently, ILs have been studied as promising substitutes for conventional electrolytes for electrochemical applications, both as bulk liquids or confined in polymer matrices, commonly known as ionogels, which have the advantages of not leaking and enhancing safety and manipulation during device assembly. For this work, the ionogel of the IL 1-Ethyl-3-methylimidazolium bis(trifluoromethylsulfonyl)imide ([C₂C₁Im][TFSI]) was synthesized by the polymerization of Tetramethyl orthosilicate (TMOS) and Dimethyldimethoxysilane (DMDMS). Thermal analyses of the pure ionic liquid and electrochemical response of the ionogel were studied in comparison with the corresponding bulk IL by using differential scanning calorimetry (DSC), thermogravimetry (TGA) and broad-band dielectric spectroscopy (BBDS), respectively. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 691 KiB

Open AccessProceeding Paper

Absorption of Free Radicals of New S-Derivatives (1,2,4-Triazole-3(2H)-yl)methyl)thiopyrimidines

by Yuriy Karpenko

Chem. Proc. 2024, 16(1), 62; https://doi.org/10.3390/ecsoc-28-20181 - 14 Nov 2024

Cited by 1 | Viewed by 442

Abstract

At the current stage of organic chemistry development, various fundamental synthetic approaches have been developed for the synthesis of 1,2,4-triazole and pyrimidine scaffolds, which demonstrate diverse biological effects. The relevance of this research lies in the combination of two pharmacophore fragments in one [...] Read more.

At the current stage of organic chemistry development, various fundamental synthetic approaches have been developed for the synthesis of 1,2,4-triazole and pyrimidine scaffolds, which demonstrate diverse biological effects. The relevance of this research lies in the combination of two pharmacophore fragments in one molecule—a pyrimidine and an azole heterocycle—connected by a thiomethylene bridge, which is expected to improve solubility and enhance known biological properties, as well as introduce new ones. This study presents the synthesis of compounds and investigates their antiradical activity applying the DPPH free radical method. Three compounds demonstrate greater activity than the reference drug, the natural antioxidant ascorbic acid. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 191 KiB

Open AccessProceeding Paper

Evaluation of Antifungal and Antioxidant Activities and Determination of Total Phenolic Compounds of Ethanolic Extract from Juglans Regia Bark

by Kaddour Faiza

Chem. Proc. 2024, 16(1), 63; https://doi.org/10.3390/ecsoc-28-20177 - 14 Nov 2024

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Abstract

Juglans regia (walnut tree) belongs to the Juglandaceae family and the Juglans genus, and is widely used in traditional medicine for its therapeutic effects. The purpose of the present work was to evaluate the in vitro antifungal and antioxidant activity of ethanolic extracts [...] Read more.

Juglans regia (walnut tree) belongs to the Juglandaceae family and the Juglans genus, and is widely used in traditional medicine for its therapeutic effects. The purpose of the present work was to evaluate the in vitro antifungal and antioxidant activity of ethanolic extracts prepared from Juglans regia bark and to determine the total phenolic compounds of the prepared extracts. The results of the antifungal activity study showed that J. regia bark ethanolic extracts were active against the three tested Candida albicans yeast strains with interesting MICs values (0.039 mg/mL). For both extracts under study, the obtained results revealed appreciable antioxidant activity and a richness in total polyphenols with contents of 258 and 285 mg AGE/g of extract. The obtained data confirmed the correlation between the total phenolic compounds and biological activities of medicinal plant extracts. In addition, Juglans regia bark extracts demonstrate notable antifungal and antioxidant activities, which explains their use in traditional medicine and makes them suitable for use in pharmaceutical preparations. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

6 pages, 1220 KiB

Open AccessProceeding Paper

Formulation of Alginate- and Pectin-Based Beads Encapsulating Trichoderma for Sustainable and Efficient Agriculture

by Atália Inocêncio Ngulela, Zohra Bengharez, Imene Slamani and Selma Mahboubi

Chem. Proc. 2024, 16(1), 64; https://doi.org/10.3390/ecsoc-28-20186 - 14 Jan 2025

Viewed by 697

Abstract

The formulation of polysaccharide-based beads encapsulating Trichoderma spp. represents an eco-friendly strategy for promoting sustainable and efficient agriculture. Trichoderma, a beneficial fungus, is well known for its ability to enhance plant growth, combat phytopathogens, and improve soil health. Encapsulating Trichoderma spores in a [...] Read more.

The formulation of polysaccharide-based beads encapsulating Trichoderma spp. represents an eco-friendly strategy for promoting sustainable and efficient agriculture. Trichoderma, a beneficial fungus, is well known for its ability to enhance plant growth, combat phytopathogens, and improve soil health. Encapsulating Trichoderma spores in a polysaccharide matrix provides a protective environment that ensures their viability and facilitates their controlled release into the soil. Alginate is a natural polymer found in various species of brown algae and certain bacteria. Pectin is a heteropolysaccharide present naturally in the cell walls of all higher plants. Due to their distinctive characteristics, alginate and pectin are regarded as promising carrier materials for the encapsulation of bioactive agents. In this work, alginate (Alg) beads, pectin (Pec) beads extracted from orange peel, and Alg/Pec composite beads in a 50/50 (w/w) ratio encapsulating Trichoderma S1 (1.83 × 10⁴ conidia/mL) and S2 (1.56 × 10⁸ conidia/mL) were prepared using the ionic gelation method. The moisture content of the prepared beads was evaluated. The size and shape of the beads were determined by analyzing images obtained by an XE3910 optical microscope. The average size of the microcapsules (wet)varied from 1886 ± 6.557 μm to 1942 ± 28.688 μm. All samples were characterized by Fourier transform infrared spectroscopy (FTIR). The overall results demonstrated the successful encapsulation of Trichoderma spp. and highlighted the effects of the different formulations on the physicochemical properties of the beads. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 620 KiB

Open AccessProceeding Paper

Microwave Activation: Highly Efficient Hydrolysis of Hesperidin and Naringin and Synthesis of Their Aglycone Acetates Under Microwave Irradiation

by Omar Fandougouma, Nawel Cheikh, Didier Villemin and Nathalie Bar

Chem. Proc. 2024, 16(1), 65; https://doi.org/10.3390/ecsoc-28-20187 - 13 Jan 2025

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Abstract

Acidic hydrolysis of Hesperidin and Naringin, furnishing their aglycone moieties Hesperetin and Naringenin, respectively, is reported using sulfuric acid and water as a solvent, under microwave irradiation. This new economical procedure provides flavanones in very good yields, ~90% better than that of acid [...] Read more.

Acidic hydrolysis of Hesperidin and Naringin, furnishing their aglycone moieties Hesperetin and Naringenin, respectively, is reported using sulfuric acid and water as a solvent, under microwave irradiation. This new economical procedure provides flavanones in very good yields, ~90% better than that of acid hydrolysis in reflux. Furthermore, we describe for the first time an efficient synthesis of Hesperetin-triacetate and Naringenin-triacetate from the corresponding flavanones, in the presence of 4-(N,N-dimethylamino)-pyridine DMAP as a catalyst, under microwave irradiation. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1261 KiB

Open AccessProceeding Paper

Functionalization of Fullerene C₆₀ with Organic Carbonates in the Presence of a Grignard Reagent and Ti(Oi-Pr)₄

by Liliya Khuzina and Artur Khuzin

Chem. Proc. 2024, 16(1), 66; https://doi.org/10.3390/ecsoc-28-20108 - 14 Nov 2024

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Abstract

Fullerene C₆₀ is by far the most studied of all allotropic modifications of carbon. Chemical modification of the double bond over the years has led to the emergence of a variety of fullerene derivatives. These derivatives have now found numerous applications in [...] Read more.

Fullerene C₆₀ is by far the most studied of all allotropic modifications of carbon. Chemical modification of the double bond over the years has led to the emergence of a variety of fullerene derivatives. These derivatives have now found numerous applications in medicine, materials and supramolecular chemistry, and as efficient electron acceptors in organic photovoltaic devices. The main method for the functionalization of C₆₀ fullerenes, which makes it possible to obtain its derivatives in a preparative volume, is the Bingel–Hirsch reaction. But this method makes it possible to obtain fullerocyclopropanes containing only carboxyl substituents at the bridging carbon atom. Therefore, in order to obtain new materials, we began to study the interaction with organic carbonates in combination with Grignard reagents in the presence of Ti-containing complex catalysts. We hope that replacing the olefin in the Kulinkovich reaction with a C₆₀ fullerene molecule will lead to new and hard-to-find functionalization products of the latter. Organic carbonates were chosen as the object of study due to the fact that they are used in the industry as solvents for natural and synthetic resins, cellulose ethers, dispersants, blowing agents, emulsifiers, absorbents of hydrogen sulfide and carbon dioxide, starting materials for the industrial synthesis of fibers and plastics, as well as plasticizers, pharmaceuticals and plant protection products. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 2049 KiB

Open AccessProceeding Paper

New 1,2,4-Triazole Potential Inhibitors of Mycobacterial Imidazoleglycerol-Phosphate Dehydratase (IGPD)

by Eugenia Oleynik, Ekaterina Pyankina, Ekaterina Mitina, Ekaterina Mikhina and Andrey Matveev

Chem. Proc. 2024, 16(1), 67; https://doi.org/10.3390/ecsoc-28-20178 - 14 Nov 2024

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Abstract

A number of new 5-aminomethyl-1,2,4-triazole-3-carboxamides, demonstrating high model affinity to the IGPD catalytic site comparable with that of the native substrate, were synthesized. The derivatives obtained were tested for antimicrobial potential against M. smegmatis, a species related to M. tuberculosis. During [...] Read more.

A number of new 5-aminomethyl-1,2,4-triazole-3-carboxamides, demonstrating high model affinity to the IGPD catalytic site comparable with that of the native substrate, were synthesized. The derivatives obtained were tested for antimicrobial potential against M. smegmatis, a species related to M. tuberculosis. During the initial antimicrobial activity evaluation in vitro, some compounds investigated inhibited microbial growth. Moreover, high binding energy values calculated for compounds/enzyme’s catalytic site complexes correlated with the compounds’ antimicrobial efficacy. This suggests that the probable biological action mechanism of new 5-aminomethyl-1,2,4-triazole-3-carboxamides may be based on their binding to the catalytic site of IGPD, which provides prerequisites for further study of this class of compounds as potential IGPD inhibitors. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 323 KiB

Open AccessProceeding Paper

Olive Residues as a Source of Bioactive Compounds

by Carlos Alvarez and Margarita Gutierrez

Chem. Proc. 2024, 16(1), 68; https://doi.org/10.3390/ecsoc-28-20183 - 14 Nov 2024

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Abstract

The production of olive oils implies the generation of high quantities of solid residues and/or wastewater that may have a great impact on terrestrial and aquatic environments because of their phytotoxicity. Alperujo is a combination of liquid and solid waste from olive oil [...] Read more.

The production of olive oils implies the generation of high quantities of solid residues and/or wastewater that may have a great impact on terrestrial and aquatic environments because of their phytotoxicity. Alperujo is a combination of liquid and solid waste from olive oil processing. Few studies are known that show their high biological potential. Indeed, wastes remaining after the production of olive oil are a heterogeneous mixture of many chemical components, such as metal ions, carbohydrates, and polyphenols, that may exert different biological activities, primarily acting as antioxidants. The samples of “alperujo” were obtained as waste from industries that work on olive oil production. Three ethanolic organic extracts were prepared using solvent maceration, ultrasound and reflux extraction methods. Yields of each extract were determined and evaluated for their ability to trap free radicals, using the DPPH and ABTS assays contributing to the calculation of SC₅₀ (free radical scavenging). The extracts were subjected to preliminary phytochemical testing, analyzing phenolic content by the Folin method and heavy metal concentration using atomic absorption spectrometry. The extraction method was decisive for the yield obtained, with the reflux system being highly efficient, and the antioxidant activity shows the potential of these wastes as a source of bioactive compounds of interest for possible reuse. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 3141 KiB

Open AccessProceeding Paper

A Computational Investigation of Potential 5-HT 2C Receptor Inhibitors for Treating Schizophrenia by ADMET Profile Analysis, Molecular Docking, DFT, Network Pharmacology, and Molecular Dynamic Simulation

by Mohammed Raihan Uddin, Mahira Rahman, Mosammad Jannatun Nayem Rafin and Joya Datta Ripa

Chem. Proc. 2024, 16(1), 69; https://doi.org/10.3390/ecsoc-28-20242 - 16 Jan 2025

Viewed by 594

Abstract

Background: Schizophrenia manifests through behavioral abnormalities, suicidal ideation, and neuropsychological deficits. Hence, this study focused on 5-hydroxytryptamine (5-HT 2C) which influenced the modulation of the series of events that lead to schizophrenia. Methodology: Based on the computational study, the potential 5-HT 2C inhibitors [...] Read more.

Background: Schizophrenia manifests through behavioral abnormalities, suicidal ideation, and neuropsychological deficits. Hence, this study focused on 5-hydroxytryptamine (5-HT 2C) which influenced the modulation of the series of events that lead to schizophrenia. Methodology: Based on the computational study, the potential 5-HT 2C inhibitors such as Ephemeranthoquinone from Arundina graminifolia and Actinodaphnine from Litsea polyantha were determined. The candidate ligands were optimized using the Gaussian 16 software package and the DFT 6-31g (d,p) basis set. The interaction between the ligands and proteins was examined with PyRx 0.8. Additionally, pharmacokinetics was assessed using SwissADME, and Protox II for toxicity prediction. The network pharmacology study was examined by using the STRING database and the Cytoscape 3.10.1 tool. Moreover, a 100-nanosecond molecular dynamics simulation analysis using Desmond to ensure the stability of these two compounds was carried out. Result: This computational research observed that ephemeranthoquinone and actinodaphnine are the most selective 5-HT 2C inhibitors due to their docking score, optimization, and molecular dynamics simulation results. Conclusions: These compounds are required to be studied further to develop a useful 5-HT 2C inhibitors for the treatment of schizophrenia. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 772 KiB

Open AccessProceeding Paper

Design, Synthesis, and Structural Study of a Shiff Base Ligand Precursor of Metallosupramolecular Architectures

by Paula Domínguez-Carbón, Sandra Fernández-Fariña and Miguel Martínez-Calvo

Chem. Proc. 2024, 16(1), 70; https://doi.org/10.3390/ecsoc-28-20142 - 14 Nov 2024

Viewed by 185

Abstract

The spontaneous association of organic ligands and metal ions has given rise to what is known as metallosupramolecular chemistry. This emerging field of chemistry has gathered significant attention due to the numerous supramolecular structures that can be obtained, which have applications in diverse [...] Read more.

The spontaneous association of organic ligands and metal ions has given rise to what is known as metallosupramolecular chemistry. This emerging field of chemistry has gathered significant attention due to the numerous supramolecular structures that can be obtained, which have applications in diverse areas, such as materials chemistry, biomedical chemistry, and catalysis, among others. In this context, Schiff base ligands are among the most commonly used ligands for the synthesis of helicates and mesocates. In this study, the Schiff base ligand H₂L was designed, synthesized, and characterized. This ligand is potentially dianionic and tetradentate [N₂O₂], with a long and semiflexible spacer, making it a bicompartmental ligand that promotes the formation of dinuclear helicate compounds. Additionally, the presence of bulky tert-butyl and ethyl groups at specific positions of the skeleton is crucial for enhancing the formation of such structures instead of mesocates. The synthesis was carried out through an imine condensation reaction between two equivalents of 4-(tert-butyl)-2-hydroxybenzaldehyde and one equivalent of 4,4′-methylenebis(2,6-diethylamine) in the presence of p-toluenesulfonic acid monohydrate as a catalyst. The ligand was characterized using standard techniques, and suitable crystals were obtained for study using X-ray diffraction. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 802 KiB

Open AccessProceeding Paper

Benzo[a]phenoxazines as Potential Anti-Inflammatory Drugs

by Joana Pinto, M. Sameiro T. Gonçalves and David M. Pereira

Chem. Proc. 2024, 16(1), 71; https://doi.org/10.3390/ecsoc-28-20167 - 14 Nov 2024

Viewed by 201

Abstract

The chemical diversity of natural products provides a promising source of anti-inflammatory drugs, notably targeting COX-2, whose activity is associated with inflammatory processes and carcinogenesis. The COX-2 and LOX inhibitory capacity of several benzo[a]phenoxazines, N- and O-heterocyclic compounds, was studied. [...] Read more.

The chemical diversity of natural products provides a promising source of anti-inflammatory drugs, notably targeting COX-2, whose activity is associated with inflammatory processes and carcinogenesis. The COX-2 and LOX inhibitory capacity of several benzo[a]phenoxazines, N- and O-heterocyclic compounds, was studied. The kinetic assay results revealed that these molecules significantly inhibit COX-2 activity, highlighting their promise as potent anti-inflammatory agents. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1536 KiB

Open AccessProceeding Paper

Organocatalytic Cascade Reactions for the Synthesis and Diversification of Privileged Structures

by Alberto Medina Ortíz, David Cruz Cruz and Clarisa Villegas Gómez

Chem. Proc. 2024, 16(1), 72; https://doi.org/10.3390/ecsoc-28-20136 - 14 Nov 2024

Viewed by 199

Abstract

Herein, we present the development of new organocatalytic cascade reactions for the synthesis and diversification of privileged structures, using trienamine activation as a key step. An important feature of this process is that once it is completed, it is possible to generate new [...] Read more.

Herein, we present the development of new organocatalytic cascade reactions for the synthesis and diversification of privileged structures, using trienamine activation as a key step. An important feature of this process is that once it is completed, it is possible to generate new reactive species within the same molecule. In this sense, a series of consecutive reactions can be carried out, incorporating dienophiles with a nucleophilic addition functionality. As a result, complex and diverse compounds can be accessed through simple starting materials. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1948 KiB

Open AccessProceeding Paper

Synthesis, Self-Assembling and Photophysical Property Exploration of Water Self-Dispersible, Grafted Poly(p-Phenylene Vinylene)s with Nonionic, Hydrophilic and Biocompatible Side Chains

by Anca-Dana Bendrea, Demet Göen-Colak, Luminita Cianga, Elena-Gabriela Hitruc, Ioan Cianga and Mariana Pinteala

Chem. Proc. 2024, 16(1), 73; https://doi.org/10.3390/ecsoc-28-20198 - 14 Nov 2024

Viewed by 204

Abstract

Conjugated polymers (CPs), in particular poly(p-phenylene vinylene)s (PPVs), are recognized as “smart” materials with potential applications ranging from optoelectronic devices to emergent technologies and to precision medicine. The present communication reports on the synthesis and structural characterization of new dibrominated macromonomers and their [...] Read more.

Conjugated polymers (CPs), in particular poly(p-phenylene vinylene)s (PPVs), are recognized as “smart” materials with potential applications ranging from optoelectronic devices to emergent technologies and to precision medicine. The present communication reports on the synthesis and structural characterization of new dibrominated macromonomers and their derived PPVs, of rod–graft–coil architecture, whose grafted, biocompatible and hydrophilic side chains are either PEG-2000 or poly(2-methyl-2-oxazoline) or poly(2-ethyl-2-oxazoline). The Suzuki–Heck cascade reaction was used for PPVs’ obtainment. After PPVs’ structural characterization using specific techniques (such as ¹H-NMR; GPC), the micellar, fluorescent nanoparticles formed by spontaneous self-assembling during simple direct dissolution in water were evaluated using dynamic light scattering for their size, complementarily combined with Atom Force Microscopy (AFM) for their shape assessing. The PPV micelles’ photophysical properties were revealed using UV-vis spectroscopy and fluorescence measurements. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 4170 KiB

Open AccessProceeding Paper

Combining Oligothiophene with Oligo-(D, L-Lactide) into a Complex, Branched Topology Toward a Functional Interface Aimed at Biomedical Applications

by Anca-Dana Bendrea, Natalia Simionescu, Elena-Gabriela Hitruc, Luminita Cianga, Ioan Cianga and Mariana Pinteala

Chem. Proc. 2024, 16(1), 74; https://doi.org/10.3390/ecsoc-28-20257 - 15 Nov 2024

Viewed by 203

Abstract

The focus of this study is the properties of a new oligothiophene grafted with oligo-(D, L-lactide) side chains (OTh-PDLLA) that enable us to establish its prospect as a biomedical material. In this vein, OTh-PDDLA’s self-assembling capability in various solvents was established [...] Read more.

The focus of this study is the properties of a new oligothiophene grafted with oligo-(D, L-lactide) side chains (OTh-PDLLA) that enable us to establish its prospect as a biomedical material. In this vein, OTh-PDDLA’s self-assembling capability in various solvents was established by measuring its particle size using dynamic light scattering. AFM investigation of the surface topography of the films obtained from several solvents, as well as the results of the interaction with normal human gingival fibroblast (NHGF) cells, showed that OTh-PDLLA offers several ways to topographically modulate the film’s surface, which allows an easy adjustment of interactions with biological entities. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1408 KiB

Open AccessProceeding Paper

Study of Lectin-like Protein from Terminalia catappa (TC) Seeds for Its Physicochemical and Antimicrobial Properties

by Fakeha Mohammed Rehan Shaikh and Ashish Sambhaji Uzgare

Chem. Proc. 2024, 16(1), 75; https://doi.org/10.3390/ecsoc-28-20179 - 14 Nov 2024

Viewed by 277

Abstract

Lectins are a diverse group of proteins crucial in numerous biological activities. They exist in plants, animals, and microorganisms, each with unique structural and functional characteristics. Their ability to exhibit hemagglutination and specifically bind with carbohydrates allows lectins to participate in processes like [...] Read more.

Lectins are a diverse group of proteins crucial in numerous biological activities. They exist in plants, animals, and microorganisms, each with unique structural and functional characteristics. Their ability to exhibit hemagglutination and specifically bind with carbohydrates allows lectins to participate in processes like cell adhesion, immune responses, and intracellular signaling pathways. Lectins are particularly noted for their roles in counteracting viral diseases, regulating blood sugar levels, fending off pathogens, and preventing cancer progression. These natural compounds offer potential therapeutic benefits in various healthcare applications. Terminalia catappa (TC), known as Indian almond, is a large tropical tree containing flavonoids, tannins, saponins, and phytosterols with medicinal values. This research aimed to investigate the partial purification and characterization of lectins from TC seeds. The process involved extracting and partially purifying the lectin, testing it for hemagglutination assay, temperature and pH stability, EDTA dependence, effect of metal ions, specific sugar determination, and antibacterial activity. Hemagglutination activity was observed in human blood group B+. The findings suggest TC seed lectin is remarkably stable within a moderate temperature range and across a broad pH spectrum. The dependence on EDTA for hemagglutination activity indicates a potential metalloprotein nature, with notable interactions with various metal ions, except Hg²⁺. While the initial antimicrobial assessment against common bacteria yielded limited results, further studies hold promise for uncovering the full potential of TC seed lectin in healthcare and therapeutic advancements. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 4808 KiB

Open AccessProceeding Paper

Synthesis, ADME, and In Silico Molecular Docking Study of Novel N-Substituted β-Carboline Analogs as a Potential Anticancer Agent

by Sunil Gaikwad

Chem. Proc. 2024, 16(1), 76; https://doi.org/10.3390/ecsoc-28-20166 - 14 Nov 2024

Viewed by 274

Abstract

The present study designed and computationally optimized a series of novel β-carboline derivatives to investigate the interaction between designed ligands and selected proteins. Therefore, to find better intercalating agents, β-carboline was used as a basic skeleton, and a series of novel β-carboline derivatives [...] Read more.

The present study designed and computationally optimized a series of novel β-carboline derivatives to investigate the interaction between designed ligands and selected proteins. Therefore, to find better intercalating agents, β-carboline was used as a basic skeleton, and a series of novel β-carboline derivatives with various aryl groups at C-1 sites and a benzyl group at N-9 position were designed and synthesized and in silico-evaluated for their anticancer activity. The structures of the compounds were identified by employing a range of spectroscopic techniques, including IR, ¹H NMR, ¹³C NMR, and elemental analyses. The silico docking study was performed to determine the maximum interaction between designed ligands and those with protein 1pye CDK₂ inhibitor. The results of the molecular docking study with enzyme 1PYE indicate that the scores and binding modes are similar to those of the co-crystallized ligand. This similarity confirms the anticancer activity of the studied compound, suggesting its potential as a promising candidate for further development as an anticancer agent. In silico ADME prediction involves using computational methods to assess the absorption, distribution, metabolism, and excretion of compounds, as well as forecasting their drug-like properties. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 694 KiB

Open AccessProceeding Paper

Development of Quantitative Structure–Anti-Inflammatory Relationships of Alkaloids

by Cristian Rojas, Doménica Muñoz, Ivanna Cordero, Belén Tenesaca and Davide Ballabio

Chem. Proc. 2024, 16(1), 77; https://doi.org/10.3390/ecsoc-28-20159 - 14 Nov 2024

Viewed by 393

Abstract

Alkaloids are naturally occurring metabolites with a wide variety of pharmacological activities and applications in science, particularly in medicinal chemistry as anti-inflammatory drugs. Because they can be labelled as active or inactive compounds against the inflammatory biological response, the aim of this work [...] Read more.

Alkaloids are naturally occurring metabolites with a wide variety of pharmacological activities and applications in science, particularly in medicinal chemistry as anti-inflammatory drugs. Because they can be labelled as active or inactive compounds against the inflammatory biological response, the aim of this work was to calibrate quantitative structure-activity relationships (QSARs) using machine learning classifiers to predict anti-inflammatory activity based on the molecular structures of alkaloids. A dataset of 100 alkaloids (58 active and 42 inactive) was retrieved from two systematic reviews. Molecules were properly curated, and the molecular geometries of the compounds were optimized using the semi-empirical method (PM3) to calculate molecular descriptors, binary fingerprints (extended-connectivity fingerprints and path fingerprints) and MACCS (Molecular ACCess System) structural keys. Then, we calibrated the QSAR models using well-known linear and non-linear machine learning classifiers, i.e., partial least squares discriminant analysis (PLSDA), random forests (RF), adaptive boosting (AdaBoost), k-nearest neighbors (kNN), N-nearest neighbors (N3) and binned nearest neighbors (BNN). For validation purposes, the dataset was randomly split into a training set and a test set in a 70:30 ratio. When using molecular descriptors, genetic algorithms-variable subset selection (GAs-VSS) was used for supervised feature selection. During the calibration of the models, a five-fold Venetian blinds cross-validation was used to optimize the classifier parameters and to control the presence of overfitting. The performance of the models was quantified by means of the non-error rate (NER) statistical parameter. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1208 KiB

Open AccessProceeding Paper

Evaluation of the Photostability of Ivermectin

by Franklin Vargas, Miguel León, Beatriz Angulo, Álvaro Álvarez, Jhonatan González and Alexis Maldonado

Chem. Proc. 2024, 16(1), 78; https://doi.org/10.3390/ecsoc-28-20182 - 14 Nov 2024

Viewed by 254

Abstract

Ivermectin (IVM) is a pharmaceutical antiparasitic agent with a broad range of medicinal properties that are comparable in impact to those of penicillin and aspirin. The molecule’s structural composition includes functional groups that indicate the potential for photoreactivity. However, there is a paucity [...] Read more.

Ivermectin (IVM) is a pharmaceutical antiparasitic agent with a broad range of medicinal properties that are comparable in impact to those of penicillin and aspirin. The molecule’s structural composition includes functional groups that indicate the potential for photoreactivity. However, there is a paucity of information regarding its photostability, particularly in tropical regions where parasitic diseases and intense solar radiation intersect. It would be beneficial to investigate the chemical transformation of this compound in a variety of natural aqueous environments under different irradiation sources. This knowledge gap motivated this study. Therefore, the chemical alterations of IVM were investigated in various natural aqueous media when exposed to solar radiation (UVA-Vis). In particular, an evaluation of its photostability was conducted at wavelengths of 350 and 254.5 nm. It is noteworthy that photodegradation occurred primarily at 350 nm. Additionally, IVM demonstrated photohemolytic effects on human erythrocytes, indicating phototoxicity. This suggests the presence of photoinduced mechanisms by this drug for the generation of free radicals, including singlet oxygen (¹O₂, type II mechanism), superoxide anion, and hydroxyl radical (^.O₂ and ^.OH, type I mechanism). The latter would also entail the interaction of the IVM molecule with the membrane of human red blood cells, which would signify a considerable biological impact. Furthermore, through computational calculations, potential photoproducts formed during IVM irradiation were deduced, simulating experimental conditions. Our findings contribute to an enhanced comprehension of IVM’s behavior under solar exposure, particularly in tropical contexts. Additional research is imperative to address its emerging biological activity status and potential implications for biomedical applications. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1176 KiB

Open AccessProceeding Paper

Synthesis and Characterization of a Series of Chromone–Hydrazones

by I. Hamzi

Chem. Proc. 2024, 16(1), 79; https://doi.org/10.3390/ecsoc-28-20131 - 14 Nov 2024

Viewed by 205

Abstract

Chromones, a class of aromatic heterocyclic compounds, possess intriguing biological and optical properties, making them ideal for spectroscopic detection. Hydrazones, known for their chelating abilities, can selectively bind to metal ions. This study presents a series of novel chromone–hydrazone derivatives synthesized from 3-formylchromone [...] Read more.

Chromones, a class of aromatic heterocyclic compounds, possess intriguing biological and optical properties, making them ideal for spectroscopic detection. Hydrazones, known for their chelating abilities, can selectively bind to metal ions. This study presents a series of novel chromone–hydrazone derivatives synthesized from 3-formylchromone and three different hydrazine compounds. The structures of these synthesized compounds were confirmed through spectral analysis using ¹H NMR, ¹³C NMR, and FT-IR spectroscopy. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 775 KiB

Open AccessProceeding Paper

Study of the Stability, Solubility and Geometry of the Complex of Inclusion β-CD with Nimesulide by Computer Chemistry Methods

by Ekaterina S. Barteneva, Pavel Y. Andreev, Elena V. Grekhneva and Kirill S. Efanov

Chem. Proc. 2024, 16(1), 80; https://doi.org/10.3390/ecsoc-28-20197 - 14 Nov 2024

Viewed by 175

Abstract

During this study, a molecular system was modeled: a nimesulide, β-cyclodextrin, inclusion complex. The use of the Gaussian 16W software package allowed us to optimize geometry and determine the thermochemical characteristics of molecular systems without considering a solvent. And this was also carried [...] Read more.

During this study, a molecular system was modeled: a nimesulide, β-cyclodextrin, inclusion complex. The use of the Gaussian 16W software package allowed us to optimize geometry and determine the thermochemical characteristics of molecular systems without considering a solvent. And this was also carried out in water media, accounted for by the polarized continuum model (PCM). To confirm the accuracy of the geometry of the β-cyclodextrin molecule, a structural alignment of 46 β-cyclodextrin molecules, accessible by a corresponding search query in the RCSB database, was performed. The RSMD values of carbon and oxygen atom deviations, as well as the total number of atoms aligned, were calculated. This calculation showed a complete conformational coincidence between the β-cyclodextrin structure designed by us and the RCSB database structures. This ensures the correct approach to subsequent calculations involving this structure. Quantum-mechanical modeling of the relationship was carried out in several stages with a gradual complexity of the basic set. The hybrid method of functional density B3LYP and 6-31G(d) was used. At the end of the calculation stage, on the surface of the studied complex, the potential energy of several minimal elements was detected. This means that there are several conformational forms of the molecular system with likely differences. The change in potential energies of the investigated compounds, caused by their application to optimize the in vacuum molecules of the PCM, allowed us to determine the values of the solvatization energies. The greater magnitude of these values in the complex under consideration indicates its better solubility in water compared to nimesulide. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 852 KiB

Open AccessProceeding Paper

Synthesis, Photophysics, and Potential Antifungal Activity of Benzo[a]phenoxazines

by Bárbara S. G. Guimarães, Maria João Sousa and M. Sameiro T. Gonçalves

Chem. Proc. 2024, 16(1), 81; https://doi.org/10.3390/ecsoc-28-20172 - 14 Nov 2024

Viewed by 117

Abstract

The synthesis and full characterization of new hydroxyl benzo[a]phenoxazinium chlorides with N-(di)propyl and/or N-isopropyl groups in the 5 and 9 positions are described. Photophysical studies carried out in ethanol and water revealed strong absorbances and significant fluorescence emissions at [...] Read more.

The synthesis and full characterization of new hydroxyl benzo[a]phenoxazinium chlorides with N-(di)propyl and/or N-isopropyl groups in the 5 and 9 positions are described. Photophysical studies carried out in ethanol and water revealed strong absorbances and significant fluorescence emissions at up to 676 nm. The antifungal activity was assessed against Saccharomyces cerevisiae and the results provide possible directions for further studies. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 542 KiB

Open AccessProceeding Paper

Molecular Docking Study: Application to the Epidermal Growth Factor Receptor

by Faiza Asli and Imane Bensahbane

Chem. Proc. 2024, 16(1), 82; https://doi.org/10.3390/ecsoc-28-20219 - 14 Nov 2024

Viewed by 198

Abstract

With the development of computer tools over the past 20 years, molecular modeling, and more precisely molecular docking (molecular docking), has very quickly entered the field of pharmaceutical research. Our work consists of studying the inhibition of the enzyme EGFR (1M17) involved in [...] Read more.

With the development of computer tools over the past 20 years, molecular modeling, and more precisely molecular docking (molecular docking), has very quickly entered the field of pharmaceutical research. Our work consists of studying the inhibition of the enzyme EGFR (1M17) involved in cancer with deferent inhibitors derived from quinazoline and quinoline by molecular docking. Ligands L_1 and L_2 are the best ligands for inhibiting the activity of 1M17 since they form a stable complex with this enzyme by better binding to the active site. The results obtained show that ligands L1 and L2 have weak interactions with the active site residue EGFR (1M17), which stabilize the complexes formed with these ligands, allow better binding at the level of the active site, and give an RMSD of L_1 [1.9563 Å] and of L_2 [1.2483 Å]. All the newly designed compounds passed the pharmacokinetic analysis (ADME–TOX) (adsorption, distribution, metabolism, excretion, and other physicochemical tests), passed the drug-likeness test, and also adhered to the Lipinski rule of five. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1651 KiB

Open AccessProceeding Paper

Synthesis and Supramolecular Organization of para-Carboxyhydrazinylidene Derivative of 3-Nitrophenylthiazolo[3,2-a]pyrimidine

by Dilyara O. Mingazhetdinova, Artem S. Agarkov, Anna A. Nefedova, Alexander S. Ovsyannikov, Igor A. Litvinov, Svetlana E. Solovieva and Igor S. Antipin

Chem. Proc. 2024, 16(1), 83; https://doi.org/10.3390/ecsoc-28-20101 - 14 Nov 2024

Viewed by 118

Abstract

Synthesis of para-carboxyhydrazinylidene, the derivative of 3-nitrophenylthiazolo[3,2-a]pyrimidine, was successfully performed with good yields. It was established that different types of non-covalent intermolecular interaction may influence the supramolecular motif-synthesized compound. Hydrogen- and chalcogen-bonding supramolecular driving forces collectively impacted the results of [...] Read more.

Synthesis of para-carboxyhydrazinylidene, the derivative of 3-nitrophenylthiazolo[3,2-a]pyrimidine, was successfully performed with good yields. It was established that different types of non-covalent intermolecular interaction may influence the supramolecular motif-synthesized compound. Hydrogen- and chalcogen-bonding supramolecular driving forces collectively impacted the results of two types of the centrosymmetric racemic dimeric self-assembly in crystalline phase. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 565 KiB

Open AccessProceeding Paper

Potential of Application of Natural Product Nanoparticles in Hypercholesterolemia

by Laura M. Teixeira, Catarina P. Reis and Rita Pacheco

Chem. Proc. 2024, 16(1), 84; https://doi.org/10.3390/ecsoc-28-20168 - 14 Nov 2024

Viewed by 110

Abstract

Hypercholesterolemia is a condition characterized by high blood cholesterol levels. Currently, the drugs available on the market to treat hypercholesterolemia show adverse side effects, related to their chronic use. Consequently, there is an increased search effort for alternatives and complementary strategies, specifically supplements [...] Read more.

Hypercholesterolemia is a condition characterized by high blood cholesterol levels. Currently, the drugs available on the market to treat hypercholesterolemia show adverse side effects, related to their chronic use. Consequently, there is an increased search effort for alternatives and complementary strategies, specifically supplements based on natural products. Moreover, various studies suggest that supplements with high antioxidant activity have a vital role in the prevention of various diseases. In this work, an aqueous avocado extract was prepared and characterized to assess its potential in hypercholesterolemia. Also, a delivery nanosystem using albumin nanoparticles was developed to use this extract as a food supplement. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 342 KiB

Open AccessProceeding Paper

Efficient Synthesis of Substituted 2-Nitrochalcone Derivatives

by Alam Yair Hidalgo, Quirino Torres-Sauret, Carlos Ernesto Lobato-García, Miguel Ángel Vilchis-Reyes, Abraham Gómez-Rivera, Oswaldo Hernandez-Abreu and Nancy Romero-Ceronio

Chem. Proc. 2024, 16(1), 85; https://doi.org/10.3390/ecsoc-28-20109 - 14 Nov 2024

Viewed by 167

Abstract

Organic synthesis plays a fundamental role in medicinal chemistry, allowing the production of compounds with desirable pharmacological properties. In this context, new synthesis methods, such as the use of ultrasound, are continuously being explored to improve the efficiency and sustainability of these processes. [...] Read more.

Organic synthesis plays a fundamental role in medicinal chemistry, allowing the production of compounds with desirable pharmacological properties. In this context, new synthesis methods, such as the use of ultrasound, are continuously being explored to improve the efficiency and sustainability of these processes. In this work, the synthesis and structural characterization of 2-nitrochalcone derivatives substituted with electron-withdrawing (fluoro) and electron-donating (methoxy) groups in the three isomeric positions of the B ring via nuclear magnetic resonance and ultrasound are presented; both a conventional method and a nonconventional ultrasound-assisted method are used. The results show that both methodologies are effective for obtaining these compounds, but the conventional method presents some additional advantages in the case of these nitrochalcones, such as shorter reaction times and better reaction yields. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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12 pages, 10150 KiB

Open AccessProceeding Paper

Cobalt (II) Complex on Nanodiamond-Grafted Polyethyleneimine@Folic Acid: An Extremely Effective Nanocatalyst for Green Synthesis of 5-Substituted 1H-Tetrazole Derivatives

by Zahra Nasri, Arezoo Ramezani and Hossein Ghafuri

Chem. Proc. 2024, 16(1), 86; https://doi.org/10.3390/ecsoc-28-20132 - 14 Nov 2024

Viewed by 112

Abstract

In this paper, a novel, cost-effective, and green methodology has been investigated for the preparation of cobalt (II) nanoparticles supported on a nanodiamond-carbon-structure grafted polyethyleneimine@folic acid (ND-g-PEI@FA@Co(II)) nanocomposite. Some of the physicochemical characteristics of the synthesized efficient heterogeneous nanocatalyst, including bond formation and [...] Read more.

In this paper, a novel, cost-effective, and green methodology has been investigated for the preparation of cobalt (II) nanoparticles supported on a nanodiamond-carbon-structure grafted polyethyleneimine@folic acid (ND-g-PEI@FA@Co(II)) nanocomposite. Some of the physicochemical characteristics of the synthesized efficient heterogeneous nanocatalyst, including bond formation and functional groups, percentage of elements, crystalline phase, and surface morphology were studied using techniques such as Fourier transform infrared spectroscopy (FT-IR), Energy dispersive X-ray spectroscopy (EDS), X-ray diffraction (XRD), and field emission scanning electron microscopy (FE-SEM). Following the principles of green chemistry, this nanocatalyst has been used in the production of 5-substituted 1H-tetrazole derivatives using different benzaldehyde derivatives, sodium azide, and malononitrile agents in ethanol eco-friendly solvent with high efficiency. The mechanism of tetrazole synthesis is carried out through cascade condensations, such as Knoevenagel condensation, 1,3-dipolar cycloaddition, and tautomerization reactions. The main advantages of the ND-g-PEI@FA@Co(II) nanocatalyst include facile preparation, easy separation, minimal consumption of catalyst for a multicomponent reaction (MCR), the use of cheap and recyclable materials, excellent product yield, and reusability up to four times with good efficiency. The substrate used in this heterogeneous catalyst (ND) with appropriate thermal stability, abundant availability in large quantities, and non-toxicity are prominent features of the synthesized nanocomposite. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1796 KiB

Open AccessProceeding Paper

Regioselective Synthesis of Coumarin-Annulated Polycyclic Heterocycles via Sequential Claisen Rearrangement and Radical Cyclization Reaction

by Pradip Debnath

Chem. Proc. 2024, 16(1), 87; https://doi.org/10.3390/ecsoc-28-20127 - 14 Nov 2024

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Abstract

Coumarin and its annulated heterocycles are mainly found in natural products, many of which show significant biological activities and are used extensively for the preparation of pharmaceutical products. Investigation revealed that many heterocyclic compounds fused with coumarin moiety exhibited antihelmentic, hypnotic, insecticidal, antifungal, [...] Read more.

Coumarin and its annulated heterocycles are mainly found in natural products, many of which show significant biological activities and are used extensively for the preparation of pharmaceutical products. Investigation revealed that many heterocyclic compounds fused with coumarin moiety exhibited antihelmentic, hypnotic, insecticidal, antifungal, and anti-coagulant properties. In industry, coumarin scaffolds are widely used for the preparation of drugs, agrochemicals, pesticides, and dyes. In recent studies, several coumarin derivatives have been used in materials science for the preparation of organic cell imaging materials, fluorescent biological probes, etc. Due to their immense application potential in biological science and material chemistry, much attention has been paid by researchers towards the synthesis of a new class of coumarin annulated heterocycles. In this paper, the synthesis of coumarin-annulated polycyclic heterocycles via sequential Claisen rearrangement and tin-hydride mediated radical cyclization is reported. The requisite starting materials 3-((4-chlorobut-2-yn-1-yl)oxy)-2H-chromen-2-one (1) was prepared from 3-hydroxycoumarin and 1,4-dichlorobut-2-yne. The Claisen rearrangement of 1 in refluxing chlorobenzene afforded 1-(chloromethyl)pyrano[2,3-c]chromen-5(3H)-one (2). Finally, radical cyclization reactions were carried out smoothly using ⁿBu₃SnH and AIBN in toluene at 110 °C, leading to the coumarin-annulated polycyclic heterocycles in high yields. The process is operationally simple and easy to work-up, making it convenient for the preparation of coumarin annulated heterocycles. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1761 KiB

Open AccessProceeding Paper

Multicomponent One-Pot Synthesis of Imidazo[1,2-a]pyridine Functionalized with Azides

by Diana García-García, Jorge Alejandro Tovar-Rosales, Indhira A. González-Gámez and Rocío Gámez-Montaño

Chem. Proc. 2024, 16(1), 88; https://doi.org/10.3390/ecsoc-28-20140 - 14 Nov 2024

Viewed by 136

Abstract

Imidazo[1,2-a]pyridines (IMPs) are valuable heterocycles, present in bioactive compounds and drugs. Analogs that incorporate azide moieties are useful intermediates in organic synthesis and can be used as synthetic platforms to access more complex products. Isocyanide-based multicomponent reactions such as Groebke–Blackburn–Bienaymé (GBB-3CR) are versatile [...] Read more.

Imidazo[1,2-a]pyridines (IMPs) are valuable heterocycles, present in bioactive compounds and drugs. Analogs that incorporate azide moieties are useful intermediates in organic synthesis and can be used as synthetic platforms to access more complex products. Isocyanide-based multicomponent reactions such as Groebke–Blackburn–Bienaymé (GBB-3CR) are versatile tools to synthesized IMPs, in which orthogonal reagents are included into components to increase its synthetic potential. Herein we developed a one-pot process to access IMPs functionalized with azides under mild conditions, which are synthetic platforms for further post-transformations. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 493 KiB

Open AccessProceeding Paper

Isolation and Characterization of Two Coumarin Compounds from the Chloroform Fraction of Scadoxus multiflorus (Martyn) Raf. (Amaryllidaceae)

by Olaiya Akeem Ayodele, Tijani Tawakaltu Omolara, Abdullahi Sakynah Musa and Sule Mohammed Ibrahim

Chem. Proc. 2024, 16(1), 89; https://doi.org/10.3390/ecsoc-28-20184 - 18 Feb 2025

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Abstract

In this study, the aerial parts of Scadoxus multiflorus were extracted using methanol through a maceration process. The resulting methanol crude extract was subsequently partitioned with solvents including n-hexane, chloroform, ethyl acetate, and n-butanol. Extensive column chromatography separation of the chloroform fraction, followed [...] Read more.

In this study, the aerial parts of Scadoxus multiflorus were extracted using methanol through a maceration process. The resulting methanol crude extract was subsequently partitioned with solvents including n-hexane, chloroform, ethyl acetate, and n-butanol. Extensive column chromatography separation of the chloroform fraction, followed by isocratic elution of two pooled fractions, led to the isolation of two coumarin derivatives: 2-methyl-2H-chromen-7-ol and 7-methoxy-2H-chromen-2-one. These compounds underwent various physicochemical analyses, such as chemical tests, melting point determination, and solubility assessments. Structural elucidation of the isolated compounds was conducted using UV spectroscopy, FT-IR, and 1D/2D NMR techniques. The final molecular structures were confirmed and named using ChemDraw. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 3784 KiB

Open AccessProceeding Paper

Impact of AgNP on the Inhibition of Fecal Coliforms by 3DP-Modified Chitosan Membranes

by Anthony C. Ogazi and Peter O. Osifo

Chem. Proc. 2024, 16(1), 90; https://doi.org/10.3390/ecsoc-28-20250 - 15 Nov 2024

Viewed by 119

Abstract

This study investigated the role of silver nanoparticles (AgNP) in the inhibition of fecal coliforms by 3D-printed modified chitosan filtration membranes. The composite membranes demonstrated steady improvement in antibacterial activity against the bacteria. The amount of silver ions (Ag⁺) added to [...] Read more.

This study investigated the role of silver nanoparticles (AgNP) in the inhibition of fecal coliforms by 3D-printed modified chitosan filtration membranes. The composite membranes demonstrated steady improvement in antibacterial activity against the bacteria. The amount of silver ions (Ag⁺) added to chitosan/AgNP filtration membranes affectshow well they kill microbes. An increase in the concentration of AgNP improved the chitosan matrix’s antibacterial activity and effectively reduced fecal coliforms. However, only fecal microorganisms in contact with Ag⁺ experienced complete destruction or inhibition from the modified composite membranes. The membrane surface structural layer revealed that the CS/AgNP composite consisted of carbon (C), oxygen (O), silver (Ag), and small amounts of sulfur (S). When active fecal bacteria cells came into contact with the CS/AgNP membrane structure, it was able to break down their barrier properties. The positively charged sites of the modified chitosan matrix effectively interacted with negatively charged microbial cells and eventually reduced fecal activities by 99.9%. The measured Ag concentrations in the effluent decreased over a period of time, suggesting that an increase in the volume of effluent would bring about a reduction in the concentration of Ag ions. Therefore, optimizing the amount of Ag nanoparticles in the modified chitosan composite is necessary to achieve the most favorable membrane separation performance for treating polluted surface water. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 379 KiB

Open AccessProceeding Paper

Ultrasound-Assisted Extraction of Cannabidiol from Moroccan Cannabis sativa L. (Beldia) and Antioxidant Activity of Its Fractions

by Héritier Uwikunda Serondo, Hassana Bourgane, Saïd El Kazzouli and Nabil El Brahmi

Chem. Proc. 2024, 16(1), 91; https://doi.org/10.3390/ecsoc-28-20253 - 15 Nov 2024

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Abstract

Cannabidiol (CBD), a major phytocannabinoid in Cannabis sativa, exhibits diverse therapeutic properties, as demonstrated by in silico, in vitro, and in vivo studies. These properties include cardioprotective, analgesic, anti-inflammatory, antioxidant, antitumor, neuroprotective, and anticancer effects. This study describes the ultrasound-assisted extraction, isolation, [...] Read more.

Cannabidiol (CBD), a major phytocannabinoid in Cannabis sativa, exhibits diverse therapeutic properties, as demonstrated by in silico, in vitro, and in vivo studies. These properties include cardioprotective, analgesic, anti-inflammatory, antioxidant, antitumor, neuroprotective, and anticancer effects. This study describes the ultrasound-assisted extraction, isolation, and characterization of CBD as a major product from Moroccan Cannabis sativa resin. Petroleum ether–dichloromethane (PE-DI), methanol, and water were used as extracting solvents with increasing gradient polarities. The isolation of CBD was achieved through the successive normal silica and reversed-phase RP18 silica gel column chromatography of the PE-DI fraction (7:3). The characterization was conducted using the infrared (IR) and nuclear magnetic resonance (NMR) techniques. The antioxidant activity of the fractions was assessed by the DPPH and FRAP assays. The total phenolic and total flavonoid content was measured with the Folin–Ciocalteu reagent and aluminum trichloride methods, respectively. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 2150 KiB

Open AccessProceeding Paper

Perspectives on Synthetic Adducts (Salts) of Nitroxoline^TM and 2-Aminoquinolin-8-ol as Promising Antibacterial Agents

by Tibor Maliar, Renata Gašparová and Mária Maliarová

Chem. Proc. 2024, 16(1), 92; https://doi.org/10.3390/ecsoc-28-20260 - 15 Nov 2024

Viewed by 126

Abstract

The threatening phenomenon of antibiotic failure in the future determines the intensive research of antibacterial active compounds, which are promising candidates as antibiotics. Quinolines, with only the representative in clinical practice being Nitroxoline^TM, are, in addition to being effective beta-lactams, macrolides, [...] Read more.

The threatening phenomenon of antibiotic failure in the future determines the intensive research of antibacterial active compounds, which are promising candidates as antibiotics. Quinolines, with only the representative in clinical practice being Nitroxoline^TM, are, in addition to being effective beta-lactams, macrolides, tetracyclines, and other antibiotic categories, forgotten antibiotics. The antibacterial efficiency of Nitroxoline^TM and 2-aminoquinolin-8-ol on eight selected highly resistant bacterial species that are the most problematic (Klebsiella ssp., Enterococcus ssp., Pseudomonas aeruginosa, Acinetobacter baumannii, and Staphylococcus aureus) could lead to higher solubility and thus bioavailability and increased antibacterial effects. In the first phase, the basic salts of Nitroxoline^TM, with sodium hydroxide, benzylamine, 4-(aminomethyl)pyridine, and other primary amines, were synthesized. In the second phase, the corresponding acidic salts of 2-aminoquinolin-8-ol were synthesized with the following acids: oxalic acid, pyrazine-2,3-dicarboxylic acid, chelidonic acid, quinaldic acid, 3,5-dinitrosalycilic acid, quinoline-2-carboxylic acid, quinoline-3-carboxylic acid, kynurenic acid, and xanthurenic acid. Nitroxoline^TM and 2-aminoquinolin-8-ol both demonstrated moderate antibacterial effects, with the average value for the eight mentioned bacterial strains being 16 mg/L (84 μM) and 50 mg/L (301 μM), respectively. The synthetized salts of both quinolinols demonstrated significantly higher solubility and slightly increased antibacterial activity. The identity and purity of the prepared products were determined by NMR and IR spectroscopy. The MW values of both quinolinols are relatively low and offer better use of the largest molecule limit, defined by Lipinski’s rule of five at 500 g/M. The options of amines and acids offer the achievement of quaternary salts with improved antibacterial activity. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

8 pages, 1813 KiB

Open AccessProceeding Paper

The Heterocyclization of 2-Imino-2H-chromeno-3-carbonitriles with Some N,N-Binucleophiles

by Anna A. Meshcheryakova, Ekaterina A. Konstantinova, Karina A. Melkonyan, Daria V. Vidlatskaya and Vitaliy V. Sorokin

Chem. Proc. 2024, 16(1), 93; https://doi.org/10.3390/ecsoc-28-20246 - 15 Nov 2024

Viewed by 112

Abstract

We investigated one-pot, three-component, and stepwise reactions of malononitrile and salicylic aldehydes (salicylic, 5-bromsalicylic) with N,N-nucleophiles, such as hydrazine hydrate, nitrobenzhydrazides, and o-phenylenediamine, under various conditions. This work reports on the synthesis of novel chromeno[4,3-c]pyrazoles and chromeno[4,3-e][1,4]diazepines. The influence of reaction parameters, such [...] Read more.

We investigated one-pot, three-component, and stepwise reactions of malononitrile and salicylic aldehydes (salicylic, 5-bromsalicylic) with N,N-nucleophiles, such as hydrazine hydrate, nitrobenzhydrazides, and o-phenylenediamine, under various conditions. This work reports on the synthesis of novel chromeno[4,3-c]pyrazoles and chromeno[4,3-e][1,4]diazepines. The influence of reaction parameters, such as solvent type and temperature, was studied. The structures of the synthesized compounds were established using spectroscopic data (IR, NMR). Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1860 KiB

Open AccessProceeding Paper

A New Synthesis of Polyhydroxylated Cyclopentane β-Amino Acids from Nitro Sugars

by Ramón J. Estévez, Begoña Pampín, Marcos González and Juan C. Estévez

Chem. Proc. 2024, 16(1), 94; https://doi.org/10.3390/ecsoc-28-20145 - 20 Feb 2025

Viewed by 277

Abstract

A ne stereocontrolled nitro sugar-mediated synthesis of polyhydroxylated β-amino acids is reported. The key step of this approach is a Michael addition of the lithium salt of tris(phenylthio)methane (a carboxyl synthetic equivalent) to sugar nitro olefins. This is followed by the generation of [...] Read more.

A ne stereocontrolled nitro sugar-mediated synthesis of polyhydroxylated β-amino acids is reported. The key step of this approach is a Michael addition of the lithium salt of tris(phenylthio)methane (a carboxyl synthetic equivalent) to sugar nitro olefins. This is followed by the generation of the amino acid functionality by the transformation of the tris(phenylthio)methyl substituent into the carboxylic acid functionality and the reduction of the nitro group to an amino group. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1543 KiB

Open AccessProceeding Paper

Synthesis of Peptide–Nonsteroidal Anti-Inflammatory Drug Hybrid Compounds and Their Selectivity in Inhibiting the Dual Cyclooxygenase-2 (COX)–5-Lipoxygenase (LOX) System: A Docking and Molecular Dynamics Study

by Juan C. Jiménez-Cruz, Ramón Guzmán-Mejía, Pedro Navarro-Santos, Hugo A. García-Gutiérrez, Julio César Ontiveros-Rodríguez, Rafael Herrera-Bucio and Judit A. Aviña-Verduzco

Chem. Proc. 2024, 16(1), 95; https://doi.org/10.3390/ecsoc-28-20256 - 15 Nov 2024

Viewed by 147

Abstract

In this paper, the synthesis of compounds based on a hybrid structure combining a fenbufen analog (a nonsteroidal anti-inflammatory drug, NSAID) with amino acids or peptides is described. Additionally, a detailed molecular docking analysis was performed to investigate their drug–receptor interactions with inflammation-related [...] Read more.

In this paper, the synthesis of compounds based on a hybrid structure combining a fenbufen analog (a nonsteroidal anti-inflammatory drug, NSAID) with amino acids or peptides is described. Additionally, a detailed molecular docking analysis was performed to investigate their drug–receptor interactions with inflammation-related enzymes COX-2 and 5-LOX. The hybrid compound that demonstrated the best interaction was further evaluated through molecular dynamics simulations, and its binding free energy (ΔG) was calculated using the Molecular Mechanics Poisson–Boltzmann Surface Area (MMPBSA) method. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 593 KiB

Open AccessProceeding Paper

Formulation of Casein Hydrogels

by Vanina A. Guntero, María C. Acuña, Yamile S. Aon, Leandro Gabriel Gutierrez and Cristián A. Ferretti

Chem. Proc. 2024, 16(1), 96; https://doi.org/10.3390/ecsoc-28-20174 - 14 Nov 2024

Viewed by 117

Abstract

Protein-based hydrogels have attracted considerable interest due to their biocompatibility, nontoxic properties, biodegradability, and renewable nature, as well as their being inexpensive and easy to obtain. Hydrogel properties depend on the temperature, polymer concentration, pH, crosslinking levels, salt concentrations, and aging. Casein is [...] Read more.

Protein-based hydrogels have attracted considerable interest due to their biocompatibility, nontoxic properties, biodegradability, and renewable nature, as well as their being inexpensive and easy to obtain. Hydrogel properties depend on the temperature, polymer concentration, pH, crosslinking levels, salt concentrations, and aging. Casein is a natural protein present in bovine milk (about 80%), which exists in the form of various micelles. It is composed of α-s1, α-s2, β-, and κ-casein and tends toward self-assembly. Casein-based hydrogels are suitable for use in biomedical applications. Considering their potential applications in the field of medicine, in this work, our objective is to find the best conditions for the development of a casein hydrogel with tetracaine hydrochloride as the active compound. The tetracaine hydrochloride has anesthetic properties; therefore, it would allow for a painless and comfortable treatment to be offered to the patient. Accordingly, different hydrogel formulations were proposed. The selected components were casein, glycerol, tetracaine hydrochloride, potassium carbonate, and sodium alginate. Stability and swelling tests was carried out, and apparent density, pH, and moisture content were investigated. The formulation that allowed us to obtain hydrogel with the desired properties was composed of tetracaine hydrochloride 1%, casein 2%, glycerol 50%, sodium alginate 4%, and potassium carbonate solution 18% (the percentages use the casein as the basis). Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 974 KiB

Open AccessProceeding Paper

On Novel Non-Organometallic Aryl Nucleophile in Palladium-Catalyzed Arylation

by Didier Villemin, Arnaud Jullien and Nathalie Bar

Chem. Proc. 2024, 16(1), 97; https://doi.org/10.3390/ecsoc-28-20147 - 4 Mar 2025

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Abstract

Phenylazocarboxylate is described as a novel non-organometallic aryl nucleophile in palladium-catalyzed arylation. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 2208 KiB

Open AccessProceeding Paper

Double Condensation of 3-Coumaranone with Aromatic Carbonyl Compounds Catalyzed by Brønsted Hyperacids

by Karima Boussafi, Didier Villemin and Nathalie Bar

Chem. Proc. 2024, 16(1), 98; https://doi.org/10.3390/ecsoc-28-20264 - 15 Nov 2024

Viewed by 91

Abstract

Condensation of two molecule of 3-coumaranone with aromatic carbonyl compounds is catalyzed by PFAT under microwave irradiation, new dicoumararan-3-ones are obtained. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1393 KiB

Open AccessProceeding Paper

Synthesis and In-Silico Analysis of Novel Tetrahydroquinolines and Their Antioxidant Activity

by Cristóbal Dinamarca, Mercedes Pinochet and Margarita Gutierrez

Chem. Proc. 2024, 16(1), 99; https://doi.org/10.3390/ecsoc-28-20135 - 14 Nov 2024

Viewed by 105

Abstract

Within the area of study of neurodegenerative diseases, particularly Alzheimer’s disease (AD), this research focused on the synthesis and evaluation of novel tetrahydroquinoline (THQ) derivatives with potential antioxidant activity. The toluidine N-propargylation synthesis protocol was optimized, achieving a significant increase in yield by [...] Read more.

Within the area of study of neurodegenerative diseases, particularly Alzheimer’s disease (AD), this research focused on the synthesis and evaluation of novel tetrahydroquinoline (THQ) derivatives with potential antioxidant activity. The toluidine N-propargylation synthesis protocol was optimized, achieving a significant increase in yield by using sodium carbonate and reaction temperature variation. Subsequently, four THQ compounds with alkene variation were successfully synthesized, including some which had not been previously reported in the literature. The synthesized compounds were characterized by nuclear magnetic resonance (NMR), mass spectrometry, and infrared spectroscopy (IR), which confirmed their structures and purity. In silico analyses performed with SwissADME and OSIRIS Property Explorer indicated that most of the compounds exhibited excellent drug-like characteristics and favorable pharmacokinetic profiles. Antioxidant evaluation was performed using DPPH and ABTS assays, in which all compounds demonstrated excellent antioxidant capacity, with EC50 values below 10 μg/mL in the ABTS assay, significantly outperforming the ascorbic acid control (EC50 = 35 μg/mL). The results suggest that the predominant radical-scavenging mechanism is single electron transfer (SET). This study provides a solid foundation for further investigations into the potential of THQs’ derivatives as antioxidants, and potential cholinesterase inhibitors in the context of neurodegenerative diseases such as Alzheimer’s. As a future projection, an enzymatic evaluation, including regarding mechanisms of action and the exploration of a hybrid synthesis of THQ/triazole, is proposed based on these promising results. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

5 pages, 1277 KiB

Open AccessProceeding Paper

Kinetic Study of Acid-Catalyzed Knoevenagel Condensation Between 5-Methoxy-1-Tetralone and Glyoxylic Acid

by Michelle E. Herrera, Elvia V. Cabrera, Roger S. Guanoluisa and Ullrich Stahl

Chem. Proc. 2024, 16(1), 100; https://doi.org/10.3390/ecsoc-28-20255 - 15 Nov 2024

Viewed by 155

Abstract

In this work we present, a kinetic study of the Knoevenagel condensation reaction between 5-methoxy-1-tetralone and glyoxylic acid, catalyzed by sulfuric acid, to produce (E)-2-(5-methoxy-1-oxo-3,4-dihydronaphthalen-2(1H)-ylidene)acetic acid. The reaction was carried out in a batch system at 400 rpm for [...] Read more.

In this work we present, a kinetic study of the Knoevenagel condensation reaction between 5-methoxy-1-tetralone and glyoxylic acid, catalyzed by sulfuric acid, to produce (E)-2-(5-methoxy-1-oxo-3,4-dihydronaphthalen-2(1H)-ylidene)acetic acid. The reaction was carried out in a batch system at 400 rpm for 24 h at temperatures of 75, 80 and 85 °C. The yields obtained at these temperatures were 90.30, 93.75 and 94.16%, respectively. The reaction was monitored by TLC and HPLC. For the kinetic analysis, three mathematical methods were used: integral, differential and non-linear regression. The results showed an excellent fit of the experimental data to the pseudo-first-order kinetic model. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 512 KiB

Open AccessProceeding Paper

Evaluation of Chitosan-Derived Mixed-Matrix Membranes as Potential Separators in Bioelectrochemical Systems

by Santiago Alvear Méndez, Raúl Bahamonde Soria, Daniel Arboleda, Carlos Cevallos, Chistian Alcivar, Henry Pupiales and Patricia Luis

Chem. Proc. 2024, 16(1), 101; https://doi.org/10.3390/ecsoc-28-20245 - 15 Nov 2024

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Abstract

Bioelectrochemical systems are energy-efficient devices that transform chemical energy into electrical energy or synthesize products of interest. These technologies make use of Nafion membranes that function as proton exchangers; however, these separators have some problems, such as fouling. Therefore, this research explores mixed-matrix [...] Read more.

Bioelectrochemical systems are energy-efficient devices that transform chemical energy into electrical energy or synthesize products of interest. These technologies make use of Nafion membranes that function as proton exchangers; however, these separators have some problems, such as fouling. Therefore, this research explores mixed-matrix membranes of chitosan and chitosan derivatives to determine their antimicrobial, anti-fouling, chemical stability and high-water retention properties. The results showed that these membranes could be good candidates to be used as separators in bioelectrochemical systems. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 380 KiB

Open AccessProceeding Paper

Acetylcholinesterase as a Target for Heliotridine-Type Alkaloids Isolated from Plants: A Computational Study

by Andrea Defant, Thamere Cheriet and Ines Mancini

Chem. Proc. 2024, 16(1), 102; https://doi.org/10.3390/ecsoc-28-20223 - 14 Nov 2024

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Abstract

The enzyme acetylcholinesterase (AChE) acts in mammalians and insects. Its inhibitors are considered to treat human disease and to develop insecticides. Docking calculations were performed by using AutoDock Vina and Protein–Ligand ANTSystem (PLANTS) on the Torpedo californica AChE complexes of natural pyrrolizidine alkaloids [...] Read more.

The enzyme acetylcholinesterase (AChE) acts in mammalians and insects. Its inhibitors are considered to treat human disease and to develop insecticides. Docking calculations were performed by using AutoDock Vina and Protein–Ligand ANTSystem (PLANTS) on the Torpedo californica AChE complexes of natural pyrrolizidine alkaloids previously evaluated in vitro as AChE inhibitors. Due to the known hepatoxicity of these alkaloids, the computational analysis was also directed to their activity on Drosophila melanogaster AChE (6XYU). The parameters here predicted for human and eco-toxicities may serve as a further indication in future investigations of these natural structures as scaffolds for the potential development of insecticides. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 2449 KiB

Open AccessProceeding Paper

Study of the Interaction of Benzene-1,4-dicarboxamide with Methylmalonyl Dichloride

by Anastasia Andreevna Varvarkina, Denis Andreevich Kolesnik, Polina Olegovna Levshukova, Igor Pavlovich Yakovlev and Egor Vyacheslavovich Morozov

Chem. Proc. 2024, 16(1), 103; https://doi.org/10.3390/ecsoc-28-20133 - 14 Nov 2024

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Abstract

Studies show that compounds such as 1,3-oxazine-6-ones are promising starting reagents that allow us to obtain various acyclic and heteroaromatic systems. These substances demonstrate a wide range of biological activity. Meanwhile, it is known that depending on the 1,3-oxazine cycle number in the [...] Read more.

Studies show that compounds such as 1,3-oxazine-6-ones are promising starting reagents that allow us to obtain various acyclic and heteroaromatic systems. These substances demonstrate a wide range of biological activity. Meanwhile, it is known that depending on the 1,3-oxazine cycle number in the molecule, pharmacological activity may vary. Therefore, the purpose of our work was to study the reaction of benzene-1,4-dicarboxamide with methylmalonyl dichloride, as a rational way to obtain new compounds of a given structure. This interaction can potentially lead to both mono- and bis(1,3-oxazine-6-one) derivatives. The reaction between terephthalamide and methylmalonyl dichloride was conducted at an equimolar ratio, with a twofold excess of the latter. Syntheses were carried out in two media—absolute benzene and 1,2-dichloroethane. The reaction of equimolar amounts of reagents resulted in obtaining only one product—4-(4-hydroxy-5-methyl-6-oxo-6H-1,3-oxazine-2-yl)benzamide (1). In twofold excess of methylmalonyl dichloride, only product 1 was obtained after 24 h of refluxing; after 58 h, only 2,2′-(benzene-1,4-diyl)bis(4-hydroxy-5-methyl-6H-1,3-oxazine-6-one) (2) was formed. The determination of the partial negative charge on the nitrogen atoms of the amido groups of terephthalamide and compound 1 allowed us to confirm the sequential formation firstly of the mono- (1) and then the bis(1,3-oxazine-6-one) derivative (2) in the reaction mass. The structure of the obtained compounds was proven using NMR spectroscopy on ¹H and ¹³C nuclei. When studying solvent influence on the synthesis rate, no significant differences were noted between benzene and 1,2-dichloroethane. However, the yield of 2,2′-(benzene-1,4-diyl)bis(4-hydroxy-5-methyl-6H-1,3-oxazine-6-one) during synthesis in 1,2-dichloroethane was lower—77% compared with 85% in benzene. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1236 KiB

Open AccessProceeding Paper

Formylation of 2-Methylpyrimidine-4,6-diol Under the Conditions of the Vilsmeier–Haack Reaction

by Aleksandr V. Dambaev, Denis A. Kolesnik, Igor P. Yakovlev and Tamara L. Semakova

Chem. Proc. 2024, 16(1), 104; https://doi.org/10.3390/ecsoc-28-20128 - 14 Nov 2024

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Abstract

In the course of this work, we explored the influence of the conditions of the Vilsmeier–Haack reaction for 2-methylpyrimidine-4,6-diol (1). We conducted a comparative analysis of approaches using various solvents (o-xylene, N,N-dimethylformamide (DMF), benzene, and dichloroethane) as the reaction medium, and [...] Read more.

In the course of this work, we explored the influence of the conditions of the Vilsmeier–Haack reaction for 2-methylpyrimidine-4,6-diol (1). We conducted a comparative analysis of approaches using various solvents (o-xylene, N,N-dimethylformamide (DMF), benzene, and dichloroethane) as the reaction medium, and the optimal one was selected. During the formylation of substrate 1 in these conditions, only 4,6-dihydroxy-2-methylpyrimidine-5-carbaldehyde (2) was successful. It should be noted that there was no substitution of hydroxyl groups for chlorine atoms observed in reactions with similar substrates. The structure of the resulting product 2 was proven using NMR spectroscopy on ¹H and ¹³C nuclei and by mass spectrometry. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 8185 KiB

Open AccessProceeding Paper

Design, Synthesis and Characterization of a Phosphino-Azine Ligand

by Uxía Barreiro-Sisto, Marcelino Maneiro and Rosa Pedrido

Chem. Proc. 2024, 16(1), 105; https://doi.org/10.3390/ecsoc-28-20129 - 14 Nov 2024

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Abstract

Azine compounds have recently gained significant attention due to the interesting properties that they display, which could be relevant in fields such as Pharmacology and Material Sciences. These types of ligands stand out in Coordination Chemistry because of the facilities that they exhibit [...] Read more.

Azine compounds have recently gained significant attention due to the interesting properties that they display, which could be relevant in fields such as Pharmacology and Material Sciences. These types of ligands stand out in Coordination Chemistry because of the facilities that they exhibit that make it easy to coordinate transition and post-transition metal ions. Furthermore, to the azine skeleton (C=N-N=C), the addition of other donor atoms such as sulfur, oxygen or phosphorus in the ligand increases the coordination possibilities. In this sense, we are interested in azine ligands as precursors of novel metallosupramolecular architectures. The research herein reported is focused on the synthesis and characterization of a potentially tetradentate [P₂O₂] organic phosphine-azine ligand (LP). The addition of the phosphine group to the azine skeleton allows for the stabilization of soft metal ions and the assembly of functional structures. The azine ligand LP⁸ has been prepared by a condensation reaction between two equivalents of (diphenylphosphino)benzaldehyde and one equivalent of azine monohydrate, and it was fully characterized by using several techniques such as elemental analysis, mass spectrometry, infrared spectroscopy, ¹H NMR spectroscopy and X-ray diffraction. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 3893 KiB

Open AccessProceeding Paper

Simple Synthesis of New Bioactive Nitrogenous Compounds by In Silico Study

by Amira Ait Belkacem

Chem. Proc. 2024, 16(1), 106; https://doi.org/10.3390/ecsoc-28-20251 - 15 Nov 2024

Viewed by 48

Abstract

A new derivative of nitrogenous compounds was successfully synthesized through a simple reaction, resulting in an excellent yield. These molecules underwent theoretical simulation studies to verify their anti-Alzheimer and anti-cancer effects, such as acetylcholinesterase, and tubulin. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1879 KiB

Open AccessProceeding Paper

The Effect of Oxygen on the Optical Properties of Citric Acid-Based Carbon Dots

by Federico Turco, Benedetta Maria Squeo, Francesca Villafiorita-Monteleone, Chiara Botta and Mariacecilia Pasini

Chem. Proc. 2024, 16(1), 107; https://doi.org/10.3390/ecsoc-28-20195 - 14 Nov 2024

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Abstract

In this study, the photophysical properties of CDs obtained as described in the literature from citric acid, formic acid, and urea were studied in two different solvents, water and DMSO, and under a nitrogen and oxygen atmosphere. The results indicate a possible doping [...] Read more.

In this study, the photophysical properties of CDs obtained as described in the literature from citric acid, formic acid, and urea were studied in two different solvents, water and DMSO, and under a nitrogen and oxygen atmosphere. The results indicate a possible doping effect of oxygen, which significantly impacts optical proprieties. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 4738 KiB

Open AccessProceeding Paper

Application and Synthesis of a New Hybrid Heterocyclic Derivative with Antioxidant Evaluation

by Amira Ait Belkacem, Roumaissa Djaafarou and Selma Rabhi

Chem. Proc. 2024, 16(1), 108; https://doi.org/10.3390/ecsoc-28-20125 - 14 Nov 2024

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Abstract

New hydrazinecarboximidamide derivatives were successfully synthesized with excellent yields. These compounds have been proven to be potent inhibitors of acetylcholinesterase and tubulin, and they also exhibit significant antioxidant effects. Furthermore, an ADMET study was conducted, which suggests that these compounds not only possess [...] Read more.

New hydrazinecarboximidamide derivatives were successfully synthesized with excellent yields. These compounds have been proven to be potent inhibitors of acetylcholinesterase and tubulin, and they also exhibit significant antioxidant effects. Furthermore, an ADMET study was conducted, which suggests that these compounds not only possess the potential to cross the blood-brain barrier. These findings allow us to consider this product as a promising candidate for future medicinal development, particularly in the treatment of neurodegenerative diseases and cancer. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1407 KiB

Open AccessProceeding Paper

A Refined Model of the CFTR Membrane Transporter as a Tool to Revert Misbehavior

by Pedro M. S. Suzano, Michael González-Durruthy, Ricardo J. Ferreira, Cátia A. Bonito, Margarida D. Amaral and Daniel J. V. A. dos Santos

Chem. Proc. 2024, 16(1), 109; https://doi.org/10.3390/ecsoc-28-20247 - 15 Nov 2024

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Abstract

ABC proteins are large transmembrane efflux pumps that export substrates against the concentration gradient through ATP hydrolysis. Due to their efflux capabilities, they are crucial in drug metabolism. Point mutations in ABC proteins can lead to many forms of illness by causing protein [...] Read more.

ABC proteins are large transmembrane efflux pumps that export substrates against the concentration gradient through ATP hydrolysis. Due to their efflux capabilities, they are crucial in drug metabolism. Point mutations in ABC proteins can lead to many forms of illness by causing protein misfolding and misbehavior. CFTR, or ABCC7, is a member of this transporter family, which, when mutated, can lead to cystic fibrosis, the most common life-shortening rare disease. Here, we report a refined and functional model of CFTR using in silico methods, aiming at further understanding anion permeation and the impact of different mutations on the gating mechanism to shine light on ways to reverse mutations’ effects. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 289 KiB

Open AccessProceeding Paper

Multi-Target In Silico Evaluation of New 2-Pyrazolines as Antimicrobial Agents

by Zukhruf Salami, Asmau Hamza, Abdullahi Idris and Yusuf Jimoh

Chem. Proc. 2024, 16(1), 110; https://doi.org/10.3390/ecsoc-28-20226 - 21 Mar 2025

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Abstract

The world today is being ravaged by the emergence and re-emergence of microbial infections caused by antimicrobial-resistant strains, brought about primarily by the frequent and perhaps unnecessary use of antimicrobial agents. A need therefore arises to develop new antimicrobial drugs that can combat [...] Read more.

The world today is being ravaged by the emergence and re-emergence of microbial infections caused by antimicrobial-resistant strains, brought about primarily by the frequent and perhaps unnecessary use of antimicrobial agents. A need therefore arises to develop new antimicrobial drugs that can combat these pathogens resistant to currently available antibiotics. This present study has adopted a multi-enzyme in silico approach in evaluating new 2-pyrazolines as antimicrobial agents, targeting and aiming to inhibit three pivotal enzymes in the bacteria’s life cycle. A library of 2-pyrazolines was tailored to achieve the desired activity. The library of compounds and amoxicillin, a standard antimicrobial drug, were docked into the molecular target enzymes. They were also subjected to toxicity and drug-likeness tests, using PROTOX and swissADME, respectively. A moderate toxicity profile was indicated, as more than 90% of the ligands were in ProTox class 4. The majority exhibited advantageous ADME characteristics. A significant number of them demonstrated a binding affinity for the target proteins that was stronger than both the native ligand and the binding affinity of amoxicillin. Ligands 30, 20, and 8 are the notable ones across all target enzymes. These results suggest that these novel ligands may be powerful inhibitors, particularly when it comes to interfering with the formation of bacterial cell walls, folic acid, and nucleotide metabolism. Additional in vivo and in vitro research is required to confirm these results and evaluate their therapeutic potential. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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508 KiB

Open AccessProceeding Paper

Hybrids of Methylxanthines and Azoderivatives as Acetylcholinesterase Inhibitors: Structure–Activity Relationship Analysis

by Brunella Biscussi, Santiago Gundin, Martina Donozo and Ana Paula Murray

Chem. Proc. 2024, 16(1), 111; https://doi.org/10.3390/ecsoc-28-20258 - 15 Nov 2024

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Abstract

In this work, we synthesized methylxanthine and azobenzene derivatives, linked to secondary amines via a seven-carbon chain, to evaluate their acetylcholinesterase (AChE) inhibitory activity. Among the azobenzene compounds, 3a exhibited the highest activity with an IC₅₀ of 1.1 µM. Meanwhile, the theobromine [...] Read more.

In this work, we synthesized methylxanthine and azobenzene derivatives, linked to secondary amines via a seven-carbon chain, to evaluate their acetylcholinesterase (AChE) inhibitory activity. Among the azobenzene compounds, 3a exhibited the highest activity with an IC₅₀ of 1.1 µM. Meanwhile, the theobromine derivative 2a was the most potent inhibitor among the methylxanthines, with an IC₅₀ of 0.19 µM. These results highlight the importance of structure–activity relationship analysis to optimize AChE inhibition by modifying pharmacophore fragments and secondary amines. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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943 KiB

Open AccessProceeding Paper

Synthesis, Characterization, and In-Silico Studies of Some Novel Phenylhydrazone Derivatives as Potential Agents for Antimicrobial Activities

by Rabiu Bako, Abdullahi Yunusa Idris, Asma’u Nasiru Hamza, Gbonjubola O. Adeshina and Musa Abdullahi Garba

Chem. Proc. 2024, 16(1), 112; https://doi.org/10.3390/ecsoc-28-20254 - 15 Nov 2024

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Abstract

Antimicrobial chemotherapeutic failure as a result of pathogenic resistance stain is great concern across the globe, there is need to search for an effective antimicrobial agent from synthetic sources to overcome emergent of microbial resistant in clinical practice. The phenylhydrazone derivatives were scientifically [...] Read more.

Antimicrobial chemotherapeutic failure as a result of pathogenic resistance stain is great concern across the globe, there is need to search for an effective antimicrobial agent from synthetic sources to overcome emergent of microbial resistant in clinical practice. The phenylhydrazone derivatives were scientifically found to have wide application in the field of drug discovery due to their anticancer, anti-tubercular, antibacterial, and antifungal activities. The (E)-Substituted-N-(phenylhydrazones) derivatives were obtained by a condensation reaction between substituted acetophenone and substituted phenyl hydrazine through a one-step reaction, resulting of five (5) novel compounds such as HS1 (E)-1-(1-(4-bromophenyl)ethylidene)-2-(2,4-dinitrophenyl)hydrazine), HS2(E)-1-(1-(4-bromophenyl)ethylidene)-2-(4-nitrophenyl)hydrazine), HS3(E)-1-(4-nitrophenyl)-2-(1-(3-nitrophenyl)ethylidene)hydrazine), HS4(E)-1-(2,4-dinitrophenyl)-2-(1-(3-nitrophenyl)ethylidene)hydrazine), and HS5 (E)-1-(1-(3-nitrophenyl)ethylidene)-2-phenylhydrazine) and the in-silico prediction of physicochemical properties were found within Lipinski’s rule of five and the synthesized compounds were established by structurally elucidations on the basis of FTIR, 1D and 2D NMR spectral analysis and the newly synthesized compounds were then subjected to antimicrobial assessment for an in vitro test evaluation using the inhibition zone technique, minimum inhibitory concentration (MIC), minimum bactericidal concentration (MBC), and minimum fungicidal concentration (MFC). Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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1310 KiB

Open AccessProceeding Paper

Synthesis of New Aza-Heterocyclic Based on 2-Pyridone

by Ikram Baba-Ahmed, Zahira Kibou, Julio A. Seijas, Noureddine Choukchou-Braham and M. Pilar Vázquez-Tato

Chem. Proc. 2024, 16(1), 113; https://doi.org/10.3390/ecsoc-28-20134 - 14 Nov 2024

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Abstract

In this work, we present new methods of synthesis of different molecules including a 2-pyridone nucleus. First, we prepared a series of 1H-free 2-pyridones and N-alkyl 2-pyridones from ethyl cyanoacetate, aromatic aldehydes, various acetophenone derivatives and ammonium acetate or diamino-alkane. [...] Read more.

In this work, we present new methods of synthesis of different molecules including a 2-pyridone nucleus. First, we prepared a series of 1H-free 2-pyridones and N-alkyl 2-pyridones from ethyl cyanoacetate, aromatic aldehydes, various acetophenone derivatives and ammonium acetate or diamino-alkane. These molecules have served as building blocks that, in conjunction with acyl chloride derivatives, glycoside derivatives, etc. have resulted in various heterocyclic hybrid structures carrying a 2-pyridone ring. Moreover, based on the cyano group reactivity of the 2-pyridone ring, we synthesized 5-pyridone 1H-tetrazole in a single step by a cycloaddition reaction [3 + 2] between 3-cyano-2-pyridone nitriles and sodium azide in the presence of metal-free L-proline. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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635 KiB

Open AccessProceeding Paper

Synthetic Pathways of trans-Substituted Porphyrins Bearing Pentafluorophenyl Groups from Dipyrromethanes

by Milena B. Boarini, Daniel A. Heredia, María E. Milanesio and Edgardo N. Durantini

Chem. Proc. 2024, 16(1), 114; https://doi.org/10.3390/ecsoc-28-20143 - 14 Nov 2024

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Abstract

Different approaches were evaluated to obtain 5,15-bis [4-(N,N-diphenyl)aminophenyl]-10,20-bis(pentafluorophenyl)porphyrin and 5,15-bis [4-(9-carbazolyl)phenyl]-10,20-bis(pentafluorophenyl)porphyrin. First, the reaction of 5-pentafluorophenyldypyrromethane with the corresponding benzaldehyde catalyzed by boron trifluoride diethyl etherate in dichloromethane led to a high level of scrambling that produced a mixture [...] Read more.

Different approaches were evaluated to obtain 5,15-bis [4-(N,N-diphenyl)aminophenyl]-10,20-bis(pentafluorophenyl)porphyrin and 5,15-bis [4-(9-carbazolyl)phenyl]-10,20-bis(pentafluorophenyl)porphyrin. First, the reaction of 5-pentafluorophenyldypyrromethane with the corresponding benzaldehyde catalyzed by boron trifluoride diethyl etherate in dichloromethane led to a high level of scrambling that produced a mixture of porphyrins. These products involve ABAB (3%), A₃B (15%), and A₄ (4%) symmetries, where A represents a pentafluorophenyl group. These porphyrins have similar polarities and they are very difficult to separate by column chromatography. Therefore, the reagents were changed to pentafluorobenzaldehyde and dipyrromethane. When a 0.5:1 molar ratio was used, A₄ porphyrin was not obtained, and the main products were ABAB (19%) and A₃B (6%). Therefore, condensation of a dipyrromethane with pentafluorobenzaldehyde provides a general method for the rational synthesis of ABAB-porphyrins in good yield with lower scrambling. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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813 KiB

Open AccessProceeding Paper

Unlocking the Potential of Fishery Waste: Acid-Soluble Ultrasound Extraction of Marine Collagen from Sardine Fish Scales

by Afaf Moufaddel, Khalid Bougrin, Hanae El Monfalouti and Badr Eddine Kartah

Chem. Proc. 2024, 16(1), 115; https://doi.org/10.3390/ecsoc-28-20194 - 14 Nov 2024

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Abstract

Globally, fish consumption generates significant waste from fish markets and processing industries, including fish skin, scales, and bones. If not appropriately managed, this fishery waste can lead to environmental pollution. Collagen, the most abundant protein in animal bodies, has diverse medical, biomedical, and [...] Read more.

Globally, fish consumption generates significant waste from fish markets and processing industries, including fish skin, scales, and bones. If not appropriately managed, this fishery waste can lead to environmental pollution. Collagen, the most abundant protein in animal bodies, has diverse medical, biomedical, and pharmaceutical applications, but its high cost has constrained its usage. Collagen derived from marine sources, particularly from the by-products of fish processing, is seen as an alternative to collagens from land animals. There has been growing interest in utilizing fish scales as a cost-effective source of this valuable collagen-rich protein. Repurposing fish scales could alleviate environmental pressure and create additional commercial value. In a recent study, collagen was isolated from the scales of Moroccan Sardina pilchardus, a fish species renowned for its high collagen content. This marine collagen type I features a triple alpha-helical structure comprising one α2 chain and two α1 chains. The collagen extraction was accomplished using the acid-soluble collagen (ASC) method combined with an ultrasound technique after pretreating the fish scales, involving a demineralization step to remove a high amount of minerals. The ASC extracted from the sardine scales exhibited high solubility in the highly acidic pH range (pH 2). Various physicochemical techniques, such as FTIR, DRX, and SEM, confirmed the isolated protein as collagen. Hence, sardine scales could serve as an alternative source of collagen, and the characteristics of the collagens were minimally affected by the extraction process employed. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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1070 KiB

Open AccessProceeding Paper

In Silico Investigation of Two Benzoxanthone-Flavonoids: ADMET Analysis and Xanthine Oxidase Binding

by Abdeslem Bouzina, Rachida Mansouri, Yousra Ouafa Bouone and Nour-Eddine Aouf

Chem. Proc. 2024, 16(1), 116; https://doi.org/10.3390/ecsoc-28-20212 - 14 Nov 2024

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Abstract

Natural products, particularly flavonoids, which possess medicinal properties such as anticancer, anti-inflammatory, and antioxidant effects, are known to inhibit the enzyme xanthine oxidase (XO), which plays a key role in purine metabolism and generates reactive oxygen species (ROS). Inhibiting XO may help manage [...] Read more.

Natural products, particularly flavonoids, which possess medicinal properties such as anticancer, anti-inflammatory, and antioxidant effects, are known to inhibit the enzyme xanthine oxidase (XO), which plays a key role in purine metabolism and generates reactive oxygen species (ROS). Inhibiting XO may help manage diseases associated with uric acid accumulation and ROS production. Molecular docking was performed to analyze the interactions of two benzoxanthone-flavonoid compounds, Artonin E and (+)-Artobiloxanthone, with the enzyme XO. These compounds demonstrated excellent stability within the site active of XO, with estimated docking scores of −9.64 and −7.99 kcal/mol, respectively, and formed significant interactions, similar to those observed in the quercetin–XO complex. Additionally, ADMET analyses suggest that these compounds have promising therapeutic potential. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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2223 KiB

Open AccessProceeding Paper

In Silico Assessment of Enaminone–Sulfanilamides as Potential Carbonic Anhydrase II Inhibitors: Molecular Docking and ADMET Prediction

by Yousra Ouafa Bouone, Abdeslem Bouzina, Rachida Mansouri and Nour-Eddine Aouf

Chem. Proc. 2024, 16(1), 117; https://doi.org/10.3390/ecsoc-28-20211 - 14 Nov 2024

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Abstract

Carbonic anhydrases (CAs) are a group of zinc-containing enzymes involved in many physiological processes through their role in the maintenance of the equilibrium between bicarbonate and CO₂ levels. Human carbonic anhydrases (hCAs) are recognized as important drug targets due to their major [...] Read more.

Carbonic anhydrases (CAs) are a group of zinc-containing enzymes involved in many physiological processes through their role in the maintenance of the equilibrium between bicarbonate and CO₂ levels. Human carbonic anhydrases (hCAs) are recognized as important drug targets due to their major implication in the development of diseases including cancer. Sulfanilamide derivatives have been widely studied and have shown remarkable efficiency in inhibiting carbonic anhydrases, with the presence of SO₂NH₂ in their structure. Therefore, the sulfonamide moiety is considered as the leading scaffold in the search for new hCA inhibitors. Moreover, the introduction of an enaminone to sulfonamide-based CA inhibitors showed an enhancement of inhibitory activity. In this context, we were interested in the in silico investigation of benzenesulfonamide derivatives containing β-enaminone that were synthesized from dicarbonyl compounds and sulfanilamide under microwave irradiation. The in silico assessment includes a molecular docking simulation against hCA II (PDB: 2AW1). The docked ligands showed good docking score values (−8.099 and −7.053 kcal.mol⁻¹), which indicates a good stability of the studied compounds within the active site. Further, significant interactions with the residues of the active site were observed, including metal coordination with Zn 262, an H-bond with Thr 199, and pi–pi stacking with the side chain of His94, which are considered as the key interactions for CA inhibition. A complementary in silico study that involved ADMET prediction was performed to learn more about the pharmacokinetic properties and the toxicity of the products in order to comprehend their ability to become drug-candidates. Full article

(This article belongs to the Proceedings of The 28th International Electronic Conference on Synthetic Organic Chemistry)

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