Previous Issue
Volume 11, Stand Alone Papers 2022
 
 

Chem. Proc., 2022, ECSOC 2022

The 26th International Electronic Conference on Synthetic Organic Chemistry

15–30 November 2022

Volume Editor: Julio A. Seijas

Number of Papers: 50
  • Issues are regarded as officially published after their release is announced to the table of contents alert mailing list.
  • You may sign up for e-mail alerts to receive table of contents of newly released issues.
  • PDF is the official format for papers published in both, html and pdf forms. To view the papers in pdf format, click on the "PDF Full-text" link, and use the free Adobe Readerexternal link to open them.
Cover Story (view full-size image): This volume compiles the complete communications presented to the 26th International Conference on Synthetic Organic Chemistry together with the contributions of twelve keynote speakers, held online [...] Read more.
Order results
Result details
Select all
Export citation of selected articles as:

Other

Proceeding Paper
Electrochemical Transformation of Bio-Derived Furans Using a Salen-Manganese Homogeneous Catalyst
Chem. Proc. 2022, 12(1), 1; https://doi.org/10.3390/ecsoc-26-13542 - 14 Nov 2022
Viewed by 197
Abstract
The electrochemical oxidation of HMF (5-hydroxymethylfurfural) to DMF (2,5-furandicarboxaldehyde) catalysed by a salen-manganese homogeneous catalyst is reported. DMF is a versatile precursor in the synthesis of functional polymers, pharmaceuticals, antifungal agents, and furan-urea resins. A manganese(III)-Schiff base complex 1 was synthetized and characterized [...] Read more.
The electrochemical oxidation of HMF (5-hydroxymethylfurfural) to DMF (2,5-furandicarboxaldehyde) catalysed by a salen-manganese homogeneous catalyst is reported. DMF is a versatile precursor in the synthesis of functional polymers, pharmaceuticals, antifungal agents, and furan-urea resins. A manganese(III)-Schiff base complex 1 was synthetized and characterized by different analytical and spectroscopic techniques. Complex 1 behaved as an efficient catalyst of the electrochemical oxidation of HMF to DMF. The conversion of HMF to DFF was performed under mild conditions. The oxidation of DFF to HMF with a conversion rate of 75% was achieved at pH 8.5, using sodium chloride as the electrolyte to increase the conductivity and to reduce the power dissipation. Full article
Show Figures

Figure 1

Proceeding Paper
In Vitro and In Silico Investigations of Natural Compounds with Predicted Activity against Neuroblastomas
Chem. Proc. 2022, 12(1), 2; https://doi.org/10.3390/ecsoc-26-13541 - 14 Nov 2022
Viewed by 208
Abstract
In the present study, the ability of an ethanolic extract from Stokesia laevis to inhibit the development of human glioblastoma cell line U87 has been investigated. Cytotoxic activity has been estimated at 78% in comparison to normal human astrocyte cell line NHA, while [...] Read more.
In the present study, the ability of an ethanolic extract from Stokesia laevis to inhibit the development of human glioblastoma cell line U87 has been investigated. Cytotoxic activity has been estimated at 78% in comparison to normal human astrocyte cell line NHA, while IC50 values were 9.12 μg of gallic acid ([GAE]) equivalents per 1 mL of extract for U87 and 24.17 μg of gallic acid ([GAE]) equivalents per 1 mL of extract for NHA. Docking simulations of the active compounds in Stokesia aster and curcumin against the target anti-apoptotic protein BCL-2 has revealed the following order in the magnitude of the docking scores: native ligand > curcumin > luteolin-7-O-glucoside > luteolin-8-O-glucoside > luteolin, with root mean square (RMS) between 0.01 and 0.93. Since neuroblastomas are not restricted by the blood–brain barrier and selective cytotoxicity has been demonstrated to be higher against tumor cells than normal control astrocytes, the use of Stokesia aster ethanolic extracts and luteolin derivates as an alternative approach to neuroblastomas is to be considered. Full article
Show Figures

Figure 1

Proceeding Paper
An Unexpected Result of Base-Promoted Rearrangement of 4a-Acetyl-8a-hydroxydecahydroquinazoline-2-thione
Chem. Proc. 2022, 12(1), 3; https://doi.org/10.3390/ecsoc-26-13568 - 14 Nov 2022
Viewed by 200
Abstract
Treatment of 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione with NaH in acetonitrile leads to its isomerization into 1-hydroxy-1-methyl-3-thioxo-2,4-diazaspiro[5.5]undecan-7-one followed by the C1-C6 bond cleavage to give N-acetyl-N’-[(2-oxocyclohexyl)methyl]thiourea. The starting compound as a single diastereomer was prepared by the reaction between the K-enolate of 2-acetylcyclohexanone and [...] Read more.
Treatment of 4a-acetyl-8a-hydroxydecahydroquinazoline-2-thione with NaH in acetonitrile leads to its isomerization into 1-hydroxy-1-methyl-3-thioxo-2,4-diazaspiro[5.5]undecan-7-one followed by the C1-C6 bond cleavage to give N-acetyl-N’-[(2-oxocyclohexyl)methyl]thiourea. The starting compound as a single diastereomer was prepared by the reaction between the K-enolate of 2-acetylcyclohexanone and N-(tosylmethyl)thiourea or N-(azidomethyl)thiourea. Full article
Show Figures

Scheme 1

Proceeding Paper
“TYC” Reaction between Alkynes and Catechol-Thiol Derivatives Prompted by Metal Nanocatalysis: Mechanism Study by DFT Calculation
Chem. Proc. 2022, 12(1), 4; https://doi.org/10.3390/ecsoc-26-13588 - 15 Nov 2022
Viewed by 258
Abstract
A recently published article by our research group demonstrated that the hydrothiolation of activated alkynes is a successful way to functionalize thiols bearing catechols. The reaction was promoted by the CuNPs/TiO2 nanocatalyst and was regio- and stereoselective towards the anti-Markovnikov Z [...] Read more.
A recently published article by our research group demonstrated that the hydrothiolation of activated alkynes is a successful way to functionalize thiols bearing catechols. The reaction was promoted by the CuNPs/TiO2 nanocatalyst and was regio- and stereoselective towards the anti-Markovnikov Z-vinyl sulfide with good to excellent yields (47–97%). The scope of the reaction was evaluated and, based on experimental observations, the reaction mechanism was investigated through DFT studies. Theoretical results and experimental data were consistent with a reaction mechanism based on a copper-catalyzed anti-Markovnikov hydrothiolation process that favors the formation of the Z-vinyl sulfide. Full article
Show Figures

Figure 1

Proceeding Paper
A Combined 2D- and 3D-QSAR Study, Design and Synthesis of Some Monocarbonyl Curcumin Analogs as Potential Inhibitors of MDA-MB-231 Breast Cancer Cells
Chem. Proc. 2022, 12(1), 5; https://doi.org/10.3390/ecsoc-26-13572 - 14 Nov 2022
Viewed by 222
Abstract
Breast cancer is the most frequently diagnosed life-threatening cancer in women. As a result, there is a critical need for the development of a safe and effective drug therapy for its treatment. Curcumin, a secondary metabolite isolated from Curcuma longa, has been [...] Read more.
Breast cancer is the most frequently diagnosed life-threatening cancer in women. As a result, there is a critical need for the development of a safe and effective drug therapy for its treatment. Curcumin, a secondary metabolite isolated from Curcuma longa, has been shown to exhibit an impressively broad range of pharmacological effects. Despite its powerful interaction with a diverse set of cellular targets, curcumin has several drawbacks that limit its potential as a therapeutic agent. One of the most common approaches to overcoming these limitations is the design and synthesis of novel curcumin analogs. This study was conducted in support of the ongoing search for new molecules that are effective enough for the treatment of triple-negative breast cancer while causing only minor side effects. Hence, several symmetric monocarbonyl analogs of curcumin with cyclopentanone, cyclohexanone and 4-piperidone as the central core were synthesized via a Claisen–Schmidt condensation reaction. Their structures were identified by measuring the melting points, as well as using FTIR and UV/VIS spectroscopic techniques. To assess the cytotoxic activities of the analogs against MDA-MB-231 breast cancer cells and to identify the significant structural features responsible for these molecules’ potency, combined 2D- and 3D-quantitative structure–activity relationship (QSAR) models were developed. The generated QSAR models demonstrated acceptable internal validation, as well as good external predictive capacity, indicating that they can be used to design similar compounds. These results suggest that the synthesized candidate drugs have promising cytotoxic potential against MDA-MB-231 cancer cells and should be further investigated both in vitro and in vivo. Full article
Show Figures

Figure 1

Proceeding Paper
Reactions of exo-exo-hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecane with Aliphatic Alcohols under the Action of Ionic Liquids
Chem. Proc. 2022, 12(1), 6; https://doi.org/10.3390/ecsoc-26-13584 - 15 Nov 2022
Viewed by 244
Abstract
It has been established for the first time that ionic liquids catalyze the alcoholysis of a hydrogenated norbornadiene dimer—exo-exo-hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecane with aliphatic C1-C4 alcohols. The reaction proceeds along the hydrocarbon cyclopropane [...] Read more.
It has been established for the first time that ionic liquids catalyze the alcoholysis of a hydrogenated norbornadiene dimer—exo-exo-hexacyclo[9.2.1.02,10.03,8.04,6.05,9]tetradecane with aliphatic C1-C4 alcohols. The reaction proceeds along the hydrocarbon cyclopropane ring by a regioselective C4-C5 bond cleavage to form the previously undescribed 4-exo-alkoxypentacyclo[8.2.1.15,8.02,9.03,7]tetradecanes in high yields, which is promising as a precursor for the synthesis of drugs, as well as in the role of transmission media. Full article
Show Figures

Figure 1

Proceeding Paper
Distal Functionalization via Transition Metal Catalysis
Chem. Proc. 2022, 12(1), 7; https://doi.org/10.3390/ecsoc-26-13690 - 17 Nov 2022
Viewed by 247
Abstract
The ubiquitous presence of sp3 C−H bonds in natural feedstock makes them inexpensive, easily accessible, and attractive synthons for the preparation of common and/or complex molecular frameworks in biologically active natural products, pharmaceutics, agrochemicals, and materials. However, the inertness of these bonds [...] Read more.
The ubiquitous presence of sp3 C−H bonds in natural feedstock makes them inexpensive, easily accessible, and attractive synthons for the preparation of common and/or complex molecular frameworks in biologically active natural products, pharmaceutics, agrochemicals, and materials. However, the inertness of these bonds due to the high bond dissociation energies and low polarity difference between the carbon and hydrogen atoms makes them challenging reaction partners. Moreover, the desired site-selectivity is often an issue in reactions with multiple analogous sp3 C−H bonds. To overcome these problems, transition metal-catalyzed C−H functionalization has been developed with the assistance of various well-designed directing groups which can coordinate to a metal center to deliver it on a targeted C−H bond through an appropriate spatial arrangement, enabling C−H activation via the formation of a cyclometalated species. However, the frequent requirement of additional steps for the construction of the directing groups and their subsequent removal after the desired operation severely hampers the efficacy and compatibility of the reactions. A promising solution would be the utilization of a transient ligand which can bind to the substrate and coordinate to the metal center in a reversible fashion. In this way, the directing group is installed, sp3 C−H functionalization occurs, and the directing group is then removed in situ without affecting the substrate function after the catalysis is finished. Overall, the whole process occurs in a single reaction pot. Herein, we are presenting our studies on transition metal-catalyzed transient directing group-enabled C−H functionalization reaction. Full article
Proceeding Paper
Synthesis, Spectral Characteristics, and Molecular Docking Studies of 2,4-Dichloro-N-(2,2,2-trichloro-1-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)amino)ethyl)benzamide
Chem. Proc. 2022, 12(1), 8; https://doi.org/10.3390/ecsoc-26-13642 - 16 Nov 2022
Viewed by 234
Abstract
Derivatives of 1,3,4-thiadiazole are of great interest for scientific and practical human activities as biologically active substances, dyes, components for creating semiconductors, energy accumulators, liquid crystals, polymers, nanomaterials, etc. Here we report the synthesis of 2,4-dichloro-N-(2,2,2-trichloro-1-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)amino)ethyl)benzamide based on N,N’ [...] Read more.
Derivatives of 1,3,4-thiadiazole are of great interest for scientific and practical human activities as biologically active substances, dyes, components for creating semiconductors, energy accumulators, liquid crystals, polymers, nanomaterials, etc. Here we report the synthesis of 2,4-dichloro-N-(2,2,2-trichloro-1-((5-(phenylamino)-1,3,4-thiadiazol-2-yl)amino)ethyl)benzamide based on N,N’-disubstituted hydrazinecarbothioamide—2,4-dichloro-N-(2,2,2-trichloro-1-(2-(phenylcarbamothioyl)-hydrazine-1-carbothioamido)ethyl)benzamide. The method for obtaining the target product is based on the dehydrosulfurization reaction of the starting hydrazinecarbothioamide under the action of a mixture of iodine and triethylamine in a DMF medium. A new derivative of 1,3,4-thiadiazole was obtained in 84% yield, and its structure was confirmed by 1H and 13C NMR spectroscopy data. Molecular docking studies were carried out with the structure of the resulting compound and dihydrofolate reductase (DHFR) in the AutoDock Vina program. The resulting compound is a potential inhibitor of DHFR and surpasses several known analogues in terms of the strength of the complex formed with the active site of this enzyme. Full article
Show Figures

Figure 1

Proceeding Paper
Organophosphorus Chemistry: Synthesis of New Phosphonic Acid Derivatives Bearing a Triazole Moiety
Chem. Proc. 2022, 12(1), 9; https://doi.org/10.3390/ecsoc-26-13585 - 15 Nov 2022
Viewed by 356
Abstract
A series of new 1,2,3-triazolylphosphonates were synthesized through multicomponent alkyne-azide 1,3-dipolar cycloaddition catalyzed by copper nanoparticles on activated carbon. The reactions were carried out in water and at a very low copper loading as green conditions, leading to the triazolylphosphonate products in moderate [...] Read more.
A series of new 1,2,3-triazolylphosphonates were synthesized through multicomponent alkyne-azide 1,3-dipolar cycloaddition catalyzed by copper nanoparticles on activated carbon. The reactions were carried out in water and at a very low copper loading as green conditions, leading to the triazolylphosphonate products in moderate to good yields. Studies into their activity as butyrylcholinesterase inhibitors are underway. Full article
Show Figures

Figure 1

Proceeding Paper
Synthetic Access to Tetracationic Benzoporphyrins and Their Role as Photosensitizers towards Gram-Negative Escherichia coli 
Chem. Proc. 2022, 12(1), 10; https://doi.org/10.3390/ecsoc-26-13587 - 15 Nov 2022
Viewed by 361
Abstract
Currently, world population faces an episode where bacteria are becoming resistant to antibiotics, and it is crucial to find alternatives and new molecules to fight these microorganisms. Photodynamic inactivation of microorganisms has been pointed out as an alternative to conventional therapies. This work [...] Read more.
Currently, world population faces an episode where bacteria are becoming resistant to antibiotics, and it is crucial to find alternatives and new molecules to fight these microorganisms. Photodynamic inactivation of microorganisms has been pointed out as an alternative to conventional therapies. This work describes the synthesis of benzoporphyrins derivatives bearing triazolyl groups and of the analogues with pyridyl units under Heck coupling conditions. The benzoporphyrin derivatives containing pyridyl groups were further quaternized with iodomethane and 1-iodopentane to evaluate the influence of alkyl chain size on their photoinactivation ability. The biological studies towards Gram-negative Escherichia coli showed that the tetracationic benzoporphyrins can efficiently inactivate this bacterium. Full article
Show Figures

Figure 1

Proceeding Paper
Carvacrol: A PLpro Inhibitor of SARS-CoV-2 Is a Natural Weapon for COVID-19
Chem. Proc. 2022, 12(1), 11; https://doi.org/10.3390/ecsoc-26-13679 - 17 Nov 2022
Viewed by 226
Abstract
The outbreak of SARS-CoV-2 created the biggest crisis to human health and has adversely affected economic growth worldwide. Several vaccines emerged from manufacturers to combat COVID-19. Unfortunately, no therapeutic medication has yet been approved by the FDA for the treatment of this disease. [...] Read more.
The outbreak of SARS-CoV-2 created the biggest crisis to human health and has adversely affected economic growth worldwide. Several vaccines emerged from manufacturers to combat COVID-19. Unfortunately, no therapeutic medication has yet been approved by the FDA for the treatment of this disease. Many researchers have performed in silico studies for the identification of potential SARS-CoV-2 inhibitors from the molecules present in Indian medicinal plants and spices. In this paper, we have performed a structure-based virtual screening (VS) of 120 compounds derived from Nigella sativa (NS) against Mpro, PLpro, and spike proteins of SARS-CoV-2. Strong binding interactions of Mpro occurred with hits NS-40 and NS-84, whereas hits NS-72D and NS-95D showed strong binding interactions with spike proteins. Interestingly, four promising hits (i.e., NS-21, NS-40, carvacrol (NS_08), and menthol) exhibited good binding interactions with both Mpro and spike proteins. Carvacrol, a monoterpenoid phenol possessing several biological activities, showed a favourable binding affinity towards the papain-like protease of SARS-CoV-2. This small molecule may be used as a natural weapon to combat COVID-19. Full article
Show Figures

Figure 1

Proceeding Paper
Conjugated Polymeric Liposomes: A Hybrid Carrier for Contemporary Drug Delivery
Chem. Proc. 2022, 12(1), 12; https://doi.org/10.3390/ecsoc-26-13640 - 16 Nov 2022
Viewed by 186
Abstract
Liposomes are artificial vesicles encapsulating the drug moiety. The structural adaptability of liposomes has been employed to make them drug carriers for smart delivery systems, improving bioavailability, stability, target delivery, etc. However, conventional liposomes have some drawbacks, such as limited payload, shorter in [...] Read more.
Liposomes are artificial vesicles encapsulating the drug moiety. The structural adaptability of liposomes has been employed to make them drug carriers for smart delivery systems, improving bioavailability, stability, target delivery, etc. However, conventional liposomes have some drawbacks, such as limited payload, shorter in vivo circulatory lifespan, unregulated releasing properties, rapid clearance from bloodstream, etc. Polymeric modification of the liposomes addressed and effectively overcame all the drawbacks of conventional liposomes. Polymeric materials offer indefinite structural diversity, thus a substantial portion of the materials has been employed for drug-targeting methods and controlled drug release. Conjugation of liposomes and polymers develops a hybrid vesicle with intermediary physicochemical and stimulus responsive properties (pH, temperature, etc.). The reliability of liposomes with respect to pH, nature of drug moiety, enzyme, and immune response can be strengthened by polymers. Polymer modified liposomes also enhance the pharmacokinetic and pharmacodynamic profile of the drug moiety. The form of polymer, cross-linking agent, interaction, and bonding used during polymerized modification of liposomes all have an impact on their activity. According to the extensive review of the literature that is accessible in the different data sources, research in this field is proactively involved in the synthesis of newer polymeric materials, and the supramolecular structuring of the different chemicals. Full article
Show Figures

Figure 1

Proceeding Paper
Construction of Lipid–Drug Conjugates for Beclomethasone Dipropionate
Chem. Proc. 2022, 12(1), 13; https://doi.org/10.3390/ecsoc-26-13528 - 14 Nov 2022
Viewed by 118
Abstract
Lipid-based nanoparticles (LBNs) are a new type of nanoparticulate drug-delivery system, which have gradually demonstrated broad prospects in pulmonary drug-delivery systems. However, the main disadvantage of these LBNs for inhalable drugs with limited lipophilicity is their low encapsulation capacity. Herein, this study anticipates [...] Read more.
Lipid-based nanoparticles (LBNs) are a new type of nanoparticulate drug-delivery system, which have gradually demonstrated broad prospects in pulmonary drug-delivery systems. However, the main disadvantage of these LBNs for inhalable drugs with limited lipophilicity is their low encapsulation capacity. Herein, this study anticipates establishing a technology platform to improve the loading capacity of low-lipophilicity drugs in LBNs for the therapy of lung diseases. A proof-of-concept study was carried out using Beclomethasone dipropionate (BDP) as a model drug. BDP was conjugated with stearic acid (SA), a kind of the lipid matrix for LBN. The conjugate was characterized and the interactions between the conjugate and SA were investigated via molecular dynamics simulation. It is expected that the drug-loading capacity of weak-lipophilic drugs in LBN can be increased by establishing the technology platform, and the application of LBNs in pulmonary delivery can be broadened. Full article
Show Figures

Figure 1

Proceeding Paper
Synthesis of N-Heterocyclic Carbene Gold Complexes Using 2,4,6-Trimethylphenyl Sydnone as Model Substrate
Chem. Proc. 2022, 12(1), 14; https://doi.org/10.3390/ecsoc-26-13674 - 17 Nov 2022
Viewed by 212
Abstract
Two gold(I) complexes have been synthesized by a two-step reaction. The first reaction step was the deprotonation with butyllithium to obtain the corresponding NHC. In the second reaction step, the metal precursor was added to afford the corresponding gold complex. At this point, [...] Read more.
Two gold(I) complexes have been synthesized by a two-step reaction. The first reaction step was the deprotonation with butyllithium to obtain the corresponding NHC. In the second reaction step, the metal precursor was added to afford the corresponding gold complex. At this point, the complex obtained depends on the nature of the metal precursor. A monocarbene complex (sydnone-Au-tht) was obtained using [Au(tht)Cl] as the metal precursor and a biscarbene complex (sydnone-Au-imidazolium) was obtained using a gold imidazolium complex as the metal precursor instead. The 13C-NMR resonance frequencies of the carbene carbon atom shifted to higher values from 97.3 to 135.6–139.7 ppm, mono and biscarbene, respectively. Full article
Show Figures

Figure 1

Proceeding Paper
Exploring BINOL-O-BODIPY-Based Dimers as Advanced Chromophoric Platforms Enabling Triplet State Population
Chem. Proc. 2022, 12(1), 15; https://doi.org/10.3390/ecsoc-26-13671 - 17 Nov 2022
Viewed by 166
Abstract
An example of a new BODIPY design with triplet state population is reported: BINOL-O-BODIPY-based dimer. This new design combines two easily accessible structural features with a demonstrated capability of populating triplet states without the need for iodine or heavy metals: meso [...] Read more.
An example of a new BODIPY design with triplet state population is reported: BINOL-O-BODIPY-based dimer. This new design combines two easily accessible structural features with a demonstrated capability of populating triplet states without the need for iodine or heavy metals: meso-p-phenylene-bridged BODIPY dimer and BINOL-O-BODIPY. Full article
Show Figures

Figure 1

Proceeding Paper
Synthesis and Chemosensory Studies of a Heterocyclic Thiosemicarbazone as a New Tributyltin Optical Chemosensor
Chem. Proc. 2022, 12(1), 16; https://doi.org/10.3390/ecsoc-26-13540 - 14 Nov 2022
Viewed by 153
Abstract
Thiosemicarbazones are a versatile type of organic compounds which are known for their coordination ability with different types of analytes, due to the presence of sulfur and nitrogen heteroatoms. Therefore, the functionalization of thiosemicarbazones with heterocyclic moieties can be a promising route to [...] Read more.
Thiosemicarbazones are a versatile type of organic compounds which are known for their coordination ability with different types of analytes, due to the presence of sulfur and nitrogen heteroatoms. Therefore, the functionalization of thiosemicarbazones with heterocyclic moieties can be a promising route to developing new optical chemosensors. Tributyltin (TBT) is an antifouling component of paints that is acutely toxic to aquatic environments, being quickly absorbed by microorganisms and causing problems such as imposex. Herein, the synthesis of a novel heterocyclic thiosemicarbazone, functionalized with a quinoline moiety, is reported to assess the potential of this recognition moiety for TBT optical chemosensing. A preliminary chemosensory study in acetonitrile solution was performed showing that 50 equivalents of TBT were needed to induce a change of color from colorless to yellow. Spectrophotometric titration was performed to assess the concentration of TBT necessary for a maximum optical signal, revealing that 100 equivalents of TBT were necessary to reach maximum absorbance, although it was able to respond with a detectable color change to a TBT concentration as low as 10 µM. Full article
Show Figures

Figure 1

Proceeding Paper
Structure-Property Influence on the Amphiphilicity of Phenolipids
Chem. Proc. 2022, 12(1), 17; https://doi.org/10.3390/ecsoc-26-13533 - 14 Nov 2022
Viewed by 165
Abstract
In recent years, increasing interest has been observed in phenolipids used for enhancing the quality of products containing lipids in the food, pharmaceutical and cosmetic industries. A better understanding of the physicochemical properties of these amphiphilic compounds is crucial to maximizing their antioxidant [...] Read more.
In recent years, increasing interest has been observed in phenolipids used for enhancing the quality of products containing lipids in the food, pharmaceutical and cosmetic industries. A better understanding of the physicochemical properties of these amphiphilic compounds is crucial to maximizing their antioxidant and antiproliferation properties. Therefore, certain p-hydroxycinnamic acid derivatives were synthesized and their lipophilicity expressed as a partition coefficient (Log P) was measured using the shake-flask method. Additionally, the obtained results were compared with the calculated data in ALOGPS 2.1. An increase in lipophilicity was observed along with an increased alkyl chain length. Moreover, hydrophilic/hydrophobic properties are closely related with the number of substituents, especially the hydroxyl group, in aromatic rings. Full article
Show Figures

Figure 1

Proceeding Paper
Phytochemistry of Uvaria narum: A Multifaceted Perspective and Ethnopharmacological Potential
Chem. Proc. 2022, 12(1), 18; https://doi.org/10.3390/ecsoc-26-13670 - 17 Nov 2022
Viewed by 191
Abstract
The blooming ethnomedicinal plant Uvaria narum (Dunal) Wall is mostly found in the deep forests of the Western Ghats and belongs to the Annonaceae family. Uvaria narum is a spreading, pubescent shrub with large, dark bluish-green leaves. Phytochemistry and pharmacognostic studies have revealed [...] Read more.
The blooming ethnomedicinal plant Uvaria narum (Dunal) Wall is mostly found in the deep forests of the Western Ghats and belongs to the Annonaceae family. Uvaria narum is a spreading, pubescent shrub with large, dark bluish-green leaves. Phytochemistry and pharmacognostic studies have revealed that the plant possesses a variety of phytochemicals that are remarkable and beneficial to humans. The plant also possesses a number of beneficial properties, such as antioxidant activity exhibited by the presence of polyphenols and tannins, antifungal activity brought on by the benzoic acid moiety, and tumour-fighting ability contributed by terpenoid and alkaloids. The presence of phytoconstituents in the plant has been attributed to the various medicinal properties of the plant, such as anticancer activity. The plant may also be considered for use against ageing and other diseases caused by free radicals. In vitro cytotoxicity is due to terpenoids, phytosterols, and flavonoids, whereas the liver is protected by flavonoids. The chemical profile of the plant shows that acetogenins, including stereoisomers, are important constituents of the root bark. Eczema, itching, varicose veins, haemorrhoids, jaundice, inflammation, and fever are the main ailments for which this herb is used. Full article
Show Figures

Figure 1

Proceeding Paper
Development of New Effective Methods for the Synthesis of Lembehynes A–C Exhibiting Cytotoxic and Neuritogenic Activity
Chem. Proc. 2022, 12(1), 19; https://doi.org/10.3390/ecsoc-26-13524 - 14 Nov 2022
Viewed by 144
Abstract
This report presents data on our studies on the preparation of the precursor lembehyne A and the complete stereoselective synthesis of natural lembehynes B and C, which have cytotoxic and neuritogenic activity. All methods and approaches to the synthesis of the above-mentioned lembehynes [...] Read more.
This report presents data on our studies on the preparation of the precursor lembehyne A and the complete stereoselective synthesis of natural lembehynes B and C, which have cytotoxic and neuritogenic activity. All methods and approaches to the synthesis of the above-mentioned lembehynes presented in this report are based on the use of the catalytic cross-cyclomagnesiation of 1,2-dienes (Dzhemilev reaction) at the key stage of the synthesis. Full article
Show Figures

Figure 1

Proceeding Paper
Aromatic Iodides: Synthesis and Conversion to Heterocycles
Chem. Proc. 2022, 12(1), 20; https://doi.org/10.3390/ecsoc-26-13641 - 16 Nov 2022
Viewed by 174
Abstract
Aromatic heterocycles can be found in many molecules endowed with specific properties, in particular for applications in the fields of medicinal chemistry and materials science. In this group, we notably develop synthetic methodologies to selectively introduce iodine onto aromatic compounds and to use [...] Read more.
Aromatic heterocycles can be found in many molecules endowed with specific properties, in particular for applications in the fields of medicinal chemistry and materials science. In this group, we notably develop synthetic methodologies to selectively introduce iodine onto aromatic compounds and to use this heavy halogen in order to build heterocycles of interest. While we sometimes employed direct iodinations on electron-enriched aromatic compounds, we mainly optimized deprotometallation–iodolysis sequences to functionalize substrates sensitive to nucleophilic attacks. In particular, hindered lithium amide–metal trap tandems have been designed to overcome the low tolerance of some functional groups (e.g., ketones or sensitive diazines) toward organolithiums. The aromatic iodides generated in these ways have been involved in transition metal–catalyzed cross-couplings to access original scaffolds (oxazoloquinoxalines, pyrazinoisatins, pyrazinocarbazoles, etc.). We specifically developed the use of aromatic iodides in the copper-mediated N-arylation of anilines, e.g., to reach triarylamines. Combined with subsequent cyclizations, these reactions allowed access to numerous heterocyclic compounds (such as acridones, acridines, other aza-aromatic polycycles and helicene-like structures) with potential applications. From some of the scaffolds obtained, biological evaluation in the frame of collaborations allowed properties of interest to be discovered (e.g., specific inhibition of protein kinases GSK-3 or PIM, related to cancer development). Full article
Show Figures

Figure 1

Proceeding Paper
In-Silico Approaches for Molecular Characterization and Structure-Based Functional Annotation of the Matrix Protein from Nipah henipavirus 
Chem. Proc. 2022, 12(1), 21; https://doi.org/10.3390/ecsoc-26-13522 - 14 Nov 2022
Viewed by 224
Abstract
Nipah henipavirus is an emerging RNA virus that poses a danger to world safety due to its high fatality rate. The Nipah virus has caused several illness epidemics in South and Southeast Asia. The matrix protein of Nipah henipavirus plays a crucial function [...] Read more.
Nipah henipavirus is an emerging RNA virus that poses a danger to world safety due to its high fatality rate. The Nipah virus has caused several illness epidemics in South and Southeast Asia. The matrix protein of Nipah henipavirus plays a crucial function in linking the viral envelope to the virus core. Connecting the viral envelope to the virus core is critical for virus assembly. Through analyses of structural and functional protein explanations, bioinformatics tools can aid in our comprehension of the protein. This study intends to provide structural and functional annotations to proteins. Using in silico approaches, the analysis also assigns the protein’s physicochemical properties, three-dimensional structure, and functional annotation. The in silico research validated the protein’s hydrophilic nature and alpha (α) helix-dominated secondary structure. The protein’s tertiary structure model is generally consistent based on various quality evaluation approaches. The functional explanation claimed that the protein is a structural protein that connects the viral envelope to the virus core, a protein that is necessary for virus assembly. This study reveals the importance of the matrix protein as a functional protein needed by Nipah henipavirus. Full article
Show Figures

Figure 1

Proceeding Paper
Synthesis of Bis (1,4-Disubstituted-1,2,3-triazoles) Starting from Diethyl Galactarate
Chem. Proc. 2022, 12(1), 22; https://doi.org/10.3390/ecsoc-26-13689 - 17 Nov 2022
Viewed by 124
Abstract
This communication reports the synthesis of a series of bis (1,4-disubstituted-1,2,3-triazoles) starting from the known (2,3,4,5) bis acetonide-protected diethyl galactarate (1). Reduction of 1 with LiAlH4 led to dioxolane 2 (90%), which, upon treatment with CBr4, gave the [...] Read more.
This communication reports the synthesis of a series of bis (1,4-disubstituted-1,2,3-triazoles) starting from the known (2,3,4,5) bis acetonide-protected diethyl galactarate (1). Reduction of 1 with LiAlH4 led to dioxolane 2 (90%), which, upon treatment with CBr4, gave the corresponding dibromide 3 (80%). The reaction of 3 with NaN3 in DMF afforded the key diazide 4 (95%). From the diazide 4 were obtained the bis (1,4-disubstituted-1,2,3 triazoles) 58 via click reactions with alkyl-substituted acetylenes, including triphenyltinacetylene. The physical characteristics of the new compounds, including selected values of 1H, 13C, and 119Sn NMR data, are given. Full article
Show Figures

Scheme 1

Proceeding Paper
Expression of β-Catenin Marker in Colorectal Cancer Cells after Treatment with Royal Jelly
Chem. Proc. 2022, 12(1), 23; https://doi.org/10.3390/ecsoc-26-13531 - 14 Nov 2022
Viewed by 112
Abstract
The deregulation of a Wnt/β-catenin signal pathway is common in colorectal cancer, while β-catenin, its crucial component, is the target for the development of many anticancer therapies. Here, we showed that royal jelly, as a well-known beneficial natural product, can affect β-catenin at [...] Read more.
The deregulation of a Wnt/β-catenin signal pathway is common in colorectal cancer, while β-catenin, its crucial component, is the target for the development of many anticancer therapies. Here, we showed that royal jelly, as a well-known beneficial natural product, can affect β-catenin at both the gene and protein level in HCT-116 colorectal cancer cell line. Our results indicate the effectiveness of royal jelly in targeting crucial markers responsible for the development and progression of cancer. Therefore, royal jelly presents a promising agent for the development of supplementary anticancer therapy. Full article
Show Figures

Figure 1

Proceeding Paper
Semisynthesis of 6β-Acetoxyvouacapane Derivatives via the Ugi-Azide Multicomponent Reaction
Chem. Proc. 2022, 12(1), 24; https://doi.org/10.3390/ecsoc-26-13552 - 14 Nov 2022
Viewed by 141
Abstract
A semisynthesis of 6β-acetoxyvouacapane-1,5-disusbtituted tetrazoles derivatives from the leaves of Caesalpinia platyloba by using the Ugi-azide multicomponent reaction as a key step reaction is described. To our knowledge, this is the first report where a non-natural product such as 1,5-disusbtituted tetrazole [...] Read more.
A semisynthesis of 6β-acetoxyvouacapane-1,5-disusbtituted tetrazoles derivatives from the leaves of Caesalpinia platyloba by using the Ugi-azide multicomponent reaction as a key step reaction is described. To our knowledge, this is the first report where a non-natural product such as 1,5-disusbtituted tetrazole has been linked to a natural product or derivate of a natural product, and beyond the biological relevance that the target molecules present, this work contributes to the area of natural products as well as multicomponent reactions. Full article
Show Figures

Figure 1

Proceeding Paper
Sulfur-Containing Homo- and Methanofullerenes: Synthesis and Study of Tribological Properties
Chem. Proc. 2022, 12(1), 25; https://doi.org/10.3390/ecsoc-26-13537 - 14 Nov 2022
Viewed by 97
Abstract
The data obtained by the authors in the field of carbon cluster chemistry, namely the catalytic cycloaddition of sulfur-containing diazo compounds to C60-fullerene under the action of complex Pd catalysts, are summarized. Cycloaddition reactions of diazoalkanes, diazoketones, and diazothioates with C [...] Read more.
The data obtained by the authors in the field of carbon cluster chemistry, namely the catalytic cycloaddition of sulfur-containing diazo compounds to C60-fullerene under the action of complex Pd catalysts, are summarized. Cycloaddition reactions of diazoalkanes, diazoketones, and diazothioates with C60-fullerene, catalyzed by Pd(acac)2–PPh3–Et3Al, with the selective formation of new sulfur-containing methano-, homo-, and pyrazolinofullerenes, are promising as modern nanosized additives in oils for highly loaded mechanisms. Full article
Show Figures

Figure 1

Proceeding Paper
Synthesis and Evaluation of an Azo Dye for the Chromogenic Detection of Metal Cations
Chem. Proc. 2022, 12(1), 26; https://doi.org/10.3390/ecsoc-26-13556 - 14 Nov 2022
Viewed by 97
Abstract
A carboxylic acid azo dye, Dabcyl, was synthesized and evaluated as a colorimetric chemosensor for metal cations with biological and environmental importance. The dye was prepared in high yield and characterized by 1H and 13C NMR and UV–Vis absorption spectroscopies. A [...] Read more.
A carboxylic acid azo dye, Dabcyl, was synthesized and evaluated as a colorimetric chemosensor for metal cations with biological and environmental importance. The dye was prepared in high yield and characterized by 1H and 13C NMR and UV–Vis absorption spectroscopies. A preliminary chemosensing study showed that Dabcyl displayed a marked color change from light yellow to pink, for Hg2+, Fe2+, Pd2+, Sn2+ and Al3+ in acetonitrile solution. Consequently, spectrophotometric titrations were carried out for this dye with selected cations, which clearly indicated that Dabcyl has potential application as a chromogenic probe for the cations under study with remarkable sensitivity and with a marked color change. Full article
Show Figures

Figure 1

Proceeding Paper
Modified Algar–Flynn–Oyamada Reaction for the Synthesis of 3-Hydroxy-2-styryl-chromen-4-ones under Solvent-Free Conditions
Chem. Proc. 2022, 12(1), 27; https://doi.org/10.3390/ecsoc-26-13558 - 14 Nov 2022
Viewed by 88
Abstract
The simple and efficient conditions for a Algar–Flynn–Oyamada reaction for the synthesis of 3-hydroxy-2-styryl-chromen-4-ones involving the grinding of different 1-(2′-hydroxy-phenyl)-5-aryl-penta-2,4-dien-1-ones with UHP (urea–hydrogen peroxide), pulverized potassium hydroxide and a few drops of ethanol at room temperature under solvent-free conditions are described. A presented [...] Read more.
The simple and efficient conditions for a Algar–Flynn–Oyamada reaction for the synthesis of 3-hydroxy-2-styryl-chromen-4-ones involving the grinding of different 1-(2′-hydroxy-phenyl)-5-aryl-penta-2,4-dien-1-ones with UHP (urea–hydrogen peroxide), pulverized potassium hydroxide and a few drops of ethanol at room temperature under solvent-free conditions are described. A presented protocol offers a faster reaction and a higher yield compared to conventional methods. The structure of the synthesized compounds was identified from their spectral data (IR, 1H-NMR). Full article
Show Figures

Scheme 1

Proceeding Paper
Preparation and Hydro-Lipophilic Properties of Monosubstituted N-Aryl-4-hydroxyquinoline-3-carboxanilides
Chem. Proc. 2022, 12(1), 28; https://doi.org/10.3390/ecsoc-26-13548 - 14 Nov 2022
Viewed by 86
Abstract
A series of twenty-two monosubstituted N-aryl-4-hydroxyquinoline-3-carboxanilides designed as dual anti-invasive agents was prepared and characterized. Lipophilicity significantly affects biological activities of compounds and ADME properties; therefore, the lipo-hydrophilic properties of these 4-hydroxyquinoline-3-carboxanilides were investigated. All the derivatives were analyzed using reversed-phase high-performance [...] Read more.
A series of twenty-two monosubstituted N-aryl-4-hydroxyquinoline-3-carboxanilides designed as dual anti-invasive agents was prepared and characterized. Lipophilicity significantly affects biological activities of compounds and ADME properties; therefore, the lipo-hydrophilic properties of these 4-hydroxyquinoline-3-carboxanilides were investigated. All the derivatives were analyzed using reversed-phase high-performance liquid chromatography. The procedure was carried out under isocratic conditions with methanol as the organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In this study, correlations between the logarithm of the capacity factor k and log P/Clog P values calculated using various methods are discussed, as well as the relationships between lipophilicity and chemical structure of the studied compounds. Full article
Show Figures

Figure 1

Proceeding Paper
Computational Revision of the Mechanism of the Thorpe Reaction
Chem. Proc. 2022, 12(1), 29; https://doi.org/10.3390/ecsoc-26-13550 - 14 Nov 2022
Viewed by 150
Abstract
The Thorpe reaction is described as a self-condensation of nitriles in the presence of a basic catalyst producing β-enaminonitriles. We performed theoretical calculations within the Density Functional Theory (DFT) framework at the ωB97XD/def2-svpd level to explore different mechanistic proposals when propionitrile is used [...] Read more.
The Thorpe reaction is described as a self-condensation of nitriles in the presence of a basic catalyst producing β-enaminonitriles. We performed theoretical calculations within the Density Functional Theory (DFT) framework at the ωB97XD/def2-svpd level to explore different mechanistic proposals when propionitrile is used as a reagent and sodium ethoxide (EtONa) as a catalyst. Furthermore, the influence of different solvents, such as ethanol (EtOH), tetrahydrofuran (THF), 1,2-dimethoxyethane (DME), and propionitrile (EtCN), was assessed. Finally, we also evaluated the effect of the fluorine group (-F), compared to the methyl group (-CH3), substituted in the α position of acetonitrile (MeCN). Our theoretical findings agree with different experimental reports on the Thorpe reaction. Full article
Show Figures

Figure 1

Proceeding Paper
Rearrangement of Imidazolidine to Piperazine Rings in the Presence of DyIII
Chem. Proc. 2022, 12(1), 30; https://doi.org/10.3390/ecsoc-26-13547 - 14 Nov 2022
Viewed by 86
Abstract
The formation of imidazolidines from secondary amines and aldehydes is well known. This small cycle can act as a nitrogen donor, and it is usually stable when it coordinates to metal ions. Sometimes, imidazolidines acting as ligands undergo breaking of the C-N bond [...] Read more.
The formation of imidazolidines from secondary amines and aldehydes is well known. This small cycle can act as a nitrogen donor, and it is usually stable when it coordinates to metal ions. Sometimes, imidazolidines acting as ligands undergo breaking of the C-N bond when coordinating to the metal center, yielding related amines. However, the reorganization of the imidazolidine into a piperazine ring is quite an unusual process. In this work, we describe the transformation of a zinc complex with a ligand containing two imidazolidine moieties into a zinc complex with a piperazine fragment as donor, in the presence of a dysprosium salt. Full article
Show Figures

Figure 1

Proceeding Paper
Use of Oxidative Coupling Strategy as a Means to Increase In Vitro Antioxidant Activity of Vanillin Derivatives
Chem. Proc. 2022, 12(1), 31; https://doi.org/10.3390/ecsoc-26-13553 - 14 Nov 2022
Viewed by 78
Abstract
The aim of this study was to investigate the antioxidant properties in vitro of three different vanillic dimmers (Compounds 1a–c). They were synthesized through an oxidative coupling strategy in good yields. The targeted compounds were found to be highly active for the [...] Read more.
The aim of this study was to investigate the antioxidant properties in vitro of three different vanillic dimmers (Compounds 1a–c). They were synthesized through an oxidative coupling strategy in good yields. The targeted compounds were found to be highly active for the total antioxidant assay, as well as for the lipid peroxidation test. All investigated compounds exhibited superior or comparable antioxidant capacity in comparison to precursor vanillin, proving that oxidative coupling is a great strategy to increase the antioxidant behavior of vanillin derivatives. Full article
Show Figures

Figure 1

Proceeding Paper
Computational Approaches for Structure-Based Molecular Characterization and Functional Annotation of the Fusion Protein of Nipah henipavirus
Chem. Proc. 2022, 12(1), 32; https://doi.org/10.3390/ecsoc-26-13530 - 14 Nov 2022
Viewed by 103
Abstract
Throughout history, viral epidemics of varying frequency and intensity have been responsible for inducing panic and causing widespread damage. The Nipah virus has one of the highest rates of fatalities of any infectious disease in the world. There have been cases when severe [...] Read more.
Throughout history, viral epidemics of varying frequency and intensity have been responsible for inducing panic and causing widespread damage. The Nipah virus has one of the highest rates of fatalities of any infectious disease in the world. There have been cases when severe respiratory distress has resulted in death, and it is known that these cases can cause encephalitis. The appearance of the virus and its ability to spread are affected by several factors. Several strategies have been created to raise awareness about the need for personal hygiene and enhance surveillance within the contaminated zone. This work aimed to determine the characteristics of a previously unidentified protein linked with the fusion of Nipah henipavirus particles. The protein’s secondary structure comprises helix, sheet, turn, and secondary coil structures. The protein is a fusion protein. In addition, the estimated Ramachandran plot provided evidence of the accuracy of the modeled protein structure. This accuracy was then verified by the Z-score-based and local model quality evaluation methods. It is possible to think of the protein as a target for developing prospective therapeutic and vaccine candidates directed against the protein to fight viral infections. Full article
Show Figures

Figure 1

Proceeding Paper
DFT Studies on the Allylation of Styrene Oxide Catalyzed by Indium Nanoparticles (InNPs)
Chem. Proc. 2022, 12(1), 33; https://doi.org/10.3390/ecsoc-26-13545 - 14 Nov 2022
Viewed by 118
Abstract
Allyl–indium species are known to smoothly react with electrophiles as epoxides. The intrinsic tension of these cyclic systems makes them very reactive starting materials, giving access to more complex products through regioselective ring-opening. In this work, indium nanoparticles (InNPs) were prepared by fast [...] Read more.
Allyl–indium species are known to smoothly react with electrophiles as epoxides. The intrinsic tension of these cyclic systems makes them very reactive starting materials, giving access to more complex products through regioselective ring-opening. In this work, indium nanoparticles (InNPs) were prepared by fast reduction of indium(III) chloride with lithium sand and a catalytic amount of 4,4′-di-tert-butylbiphenyl. InNPs were employed as catalysts for the ring-opening allylation reaction of styrene oxide with allyl or prenylbromide. All the possible reaction paths for the formation of the different alcohols were modeled applying DFT calculations, achieving good correlation between the experimental and computational results. Full article
Show Figures

Scheme 1

Proceeding Paper
Nickel-Catalyzed, One-Pot Synthesis of Pyrazoles
Chem. Proc. 2022, 12(1), 34; https://doi.org/10.3390/ecsoc-26-13687 - 17 Nov 2022
Viewed by 92
Abstract
Recently, multi-component, one-pot reactions have been shown to be efficient and environmentally friendly methods compared to traditional, linear-step syntheses. Heterogeneous catalyzed multicomponent reactions are one of the green approaches to the synthesis of organic compounds, especially pyrazoles and their derivatives. Here we demonstrate [...] Read more.
Recently, multi-component, one-pot reactions have been shown to be efficient and environmentally friendly methods compared to traditional, linear-step syntheses. Heterogeneous catalyzed multicomponent reactions are one of the green approaches to the synthesis of organic compounds, especially pyrazoles and their derivatives. Here we demonstrate the one-pot synthesis of pyrazoles using heterogeneous nickel-based catalysts for the condensation of various hydrazine, ketone derivatives, and aldehyde derivatives at room temperature. The thus synthesized heterogeneous catalyst can be reused up to the seventh cycle without much loss of catalytic activity. Full article
Show Figures

Figure 1

Proceeding Paper
Cyclopalladated Compounds with Bulky Phosphine (dppm): Synthesis, Characterization, and X-ray Diffraction
Chem. Proc. 2022, 12(1), 35; https://doi.org/10.3390/ecsoc-26-13563 - 14 Nov 2022
Viewed by 100
Abstract
The reaction between a cholro-bridged dinuclear compound (a, b) and a diphosphine (dppm) ligand in a molar ratio of 1:2 yielded a mononuclear compound [{Pd[R-C6H3C(H)=NCy]{Ph2PCH2PPh2-P,P}][PF6] {R = 3-CHO (1a), 4-CHO (1b)}. [...] Read more.
The reaction between a cholro-bridged dinuclear compound (a, b) and a diphosphine (dppm) ligand in a molar ratio of 1:2 yielded a mononuclear compound [{Pd[R-C6H3C(H)=NCy]{Ph2PCH2PPh2-P,P}][PF6] {R = 3-CHO (1a), 4-CHO (1b)}. The compounds were characterized using IR, 1H, and 31P–{1H} NMR spectroscopy, and compound 1b was identified using X-ray diffraction. Full article
Show Figures

Figure 1

Proceeding Paper
The Potential of Thiazole Derivatives as Antimicrobial Agents
Chem. Proc. 2022, 12(1), 36; https://doi.org/10.3390/ecsoc-26-13673 - 17 Nov 2022
Viewed by 201
Abstract
A transnational concern for the healthy development of human beings is antimicrobial resistance (AMR). The rising rates of microbial resistance present a serious issue for the development of human life and hence it is essential to find and create newer antimicrobial drugs with [...] Read more.
A transnational concern for the healthy development of human beings is antimicrobial resistance (AMR). The rising rates of microbial resistance present a serious issue for the development of human life and hence it is essential to find and create newer antimicrobial drugs with unique modes of action. One approach used these days to solving this challenge is the use of heterocyclics to create hybrid compounds by fusing two or more bioactive heterocyclic moieties into a single molecular platform. This study discusses the many hybrid approaches that have been used to produce possible novel antimicrobial medicines that are both safe and effective. The landscaping of heterocycles such as thiazole derivatives is covered in the current review paper. In this paper, all the extensive approaches of heterocyclic composites, primarily thiazole derivatives, exhibit vibrant biological activity. The purpose of this work is to support methods that may be used to create various thiazole derivatives and their biological activity. This paper will offer great recommendations for potential medicine designs in the future. Full article
Show Figures

Figure 1

Proceeding Paper
Synthesis of Bis-Amides Employing a Plant-Derived Triterpenoid as Component in the Ugi Reaction
Chem. Proc. 2022, 12(1), 37; https://doi.org/10.3390/ecsoc-26-13560 - 14 Nov 2022
Viewed by 98
Abstract
Herein we describe the synthesis of a series of four novel triterpenoid-derived bis-amides, employing masticadienonic acid from Pistacia mexicana as a carboxylic acid component in the Ugi reaction. Products were obtained via a facile and efficient one-pot procedure under mild green conditions, [...] Read more.
Herein we describe the synthesis of a series of four novel triterpenoid-derived bis-amides, employing masticadienonic acid from Pistacia mexicana as a carboxylic acid component in the Ugi reaction. Products were obtained via a facile and efficient one-pot procedure under mild green conditions, with moderate yields (29–58%). The stereo-electronic nature of the aldehyde component influenced the reaction yields. Full article
Show Figures

Scheme 1

Proceeding Paper
Catalytic Cycloaddition of Diazo Compounds Based on Pharmacologically Significant and Natural Compounds to C60-Fullerene
Chem. Proc. 2022, 12(1), 38; https://doi.org/10.3390/ecsoc-26-13534 - 14 Nov 2022
Viewed by 102
Abstract
The data obtained by the authors in the field of carbon cluster chemistry, namely, the catalytic cycloaddition of diazo compounds of modern pharmacologically significant and natural compounds to C60-fullerene under the action of complex Pd–catalysts, are summarized. Cycloaddition reactions of diazoacetates, [...] Read more.
The data obtained by the authors in the field of carbon cluster chemistry, namely, the catalytic cycloaddition of diazo compounds of modern pharmacologically significant and natural compounds to C60-fullerene under the action of complex Pd–catalysts, are summarized. Cycloaddition reactions of diazoacetates, diazoamides, and diazoketones with C60-fullerene, catalyzed by Pd(acac)2–PPh3–Et3Al, with the selective formation of methano– and pyrazolinofullerenes, are new and promising classes of biologically active derivatives of C60-fullerenes. Full article
Show Figures

Figure 1

Proceeding Paper
Phosphorylation of Hyaluronic Acid
Chem. Proc. 2022, 12(1), 39; https://doi.org/10.3390/ecsoc-26-13535 - 14 Nov 2022
Viewed by 91
Abstract
Chemical phosphorylation of hyaluronic acid (HA) remains an unresolved problem for the chemistry of this unique polysaccharide, since convenient phosphorylating reagents are not reactive enough to obtain HA phosphates (HA-P) with a satisfactory degree of esterification of hydroxyl groups. The synthesis of phosphates [...] Read more.
Chemical phosphorylation of hyaluronic acid (HA) remains an unresolved problem for the chemistry of this unique polysaccharide, since convenient phosphorylating reagents are not reactive enough to obtain HA phosphates (HA-P) with a satisfactory degree of esterification of hydroxyl groups. The synthesis of phosphates of low-molecular-weight (43 kDa) and high-molecular-weight (0.5–0.7 MDa) HA was undertaken using such reagents as sodium trimetaphosphate Na3P3O9, H3PO4, NaH2PO4/Na2HPO4, and anhydride P2O5. Solid-phase HA esterification with P2O5 was found to be the most convenient and efficient method. The HA-P samples were characterized by XRF and NMR spectroscopy (31P and 1H-31P) and contained, depending on the HA/P2O5 ratio, 0.30–6.25% P wt., in the form of disubstituted mono-, di-, and polyphosphates. Full article
Show Figures

Figure 1

Proceeding Paper
Benzyl Carbamates of 4-Aminosalicylanilides as Possible BACE1 Modulators
Chem. Proc. 2022, 12(1), 40; https://doi.org/10.3390/ecsoc-26-13680 - 17 Nov 2022
Viewed by 80
Abstract
Recently, a series of thirty-eight 4-{[(benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid amides designed as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors were described as potential drugs to alleviate the symptoms of Alzheimer’s disease (AD). Some of these compounds have shown promise for inhibiting either AChE or BChE. Since [...] Read more.
Recently, a series of thirty-eight 4-{[(benzyloxy)carbonyl]amino}-2-hydroxybenzoic acid amides designed as potential acetyl- and butyrylcholinesterase (AChE/BChE) inhibitors were described as potential drugs to alleviate the symptoms of Alzheimer’s disease (AD). Some of these compounds have shown promise for inhibiting either AChE or BChE. Since these compounds are structurally similar to agents inhibiting beta-site amyloid precursor protein cleaving enzyme 1 (BACE1), the aim of the contribution was to verify how our compounds were able to affect this enzyme, which, when inhibited, blocks the formation of amyloid-β, but whose inhibition is associated with significant adverse effects in humans. At a concentration of 10 µM, only benzyl {4-[(4-fluorophenyl)carbamoyl]-3-hydroxyphenyl}carbamate was found to show approximately 28% inhibition of BACE1 activity. Full article
Show Figures

Figure 1

Proceeding Paper
The Antiviral Activity of Trifluoromethylthiolane Derivatives
Chem. Proc. 2022, 12(1), 41; https://doi.org/10.3390/ecsoc-26-13643 - 16 Nov 2022
Viewed by 69
Abstract
The search for new antiviral agents is an important task today. The aim of this study was to elucidate the impact of trifluoromethylthiolane derivatives on herpetic and adenoviral infections. It was found that the 2-hydroxy-2-trifluoromethylthiolane significantly inhibited Herpes simplex virus type 1 (HSV-1) [...] Read more.
The search for new antiviral agents is an important task today. The aim of this study was to elucidate the impact of trifluoromethylthiolane derivatives on herpetic and adenoviral infections. It was found that the 2-hydroxy-2-trifluoromethylthiolane significantly inhibited Herpes simplex virus type 1 (HSV-1) reproduction, reducing the virus titer obtained de novo. Such activity indicates that virus offspring are formed, but the virus particles are not complete and are not able to cause an infection process. Therefore, trifluoromethylthiolane derivatives may be a potential compounds for the development on their basis agents for the treatment of herpetic infections. Full article
Show Figures

Figure 1

Proceeding Paper
Ti-Catalyzed Reaction of β-Pinene with BF3·THF
Chem. Proc. 2022, 12(1), 42; https://doi.org/10.3390/ecsoc-26-13529 - 14 Nov 2022
Viewed by 87
Abstract
The reaction between β-pinene and BF3·THF in the presence of the catalytic system Cp2TiCl2/Mg was carried out for the first time to obtain a 1-fluoro-substituted boraspirane, undescribed previously. The reaction proceeds stereoselectively, but is complicated by the [...] Read more.
The reaction between β-pinene and BF3·THF in the presence of the catalytic system Cp2TiCl2/Mg was carried out for the first time to obtain a 1-fluoro-substituted boraspirane, undescribed previously. The reaction proceeds stereoselectively, but is complicated by the rearrangement of the β-pinene under the Ti-catalyzed reaction conditions. Full article
Show Figures

Figure 1

Proceeding Paper
Synthesis and Evaluation of Biological Activities of Schiff Base Derivatives of 4-Aminoantipyrine and Cinnamaldehydes
Chem. Proc. 2022, 12(1), 43; https://doi.org/10.3390/ecsoc-26-13684 - 17 Nov 2022
Viewed by 117
Abstract
Schiff bases have been important compounds ever since their discovery and are both found in nature and synthesized in the laboratory. They participate in a variety of synthetic processes and possess desirable biological activity, including antibacterial, anti-inflammatory, antioxidant, and anticancer activity, among others. [...] Read more.
Schiff bases have been important compounds ever since their discovery and are both found in nature and synthesized in the laboratory. They participate in a variety of synthetic processes and possess desirable biological activity, including antibacterial, anti-inflammatory, antioxidant, and anticancer activity, among others. In this study, eight Schiff bases derived from the reaction of 4-aminoantipyrine with various cinnamaldehydes have been synthesized and characterized. All derivatives were tested in vitro on several human carcinoma cell lines to determine their antitumor activity and against different bacteria strains of clinical and food industry importance to evaluate their antibacterial activity. Several of the Schiff bases evaluated inhibited tumor cell growth in a dose-dependent manner. The compound that exhibited the most activity against all cell lines had IC50 values of less than 18 μM. On the other hand, during the evaluation of the antibacterial activity, only two Schiff base derivatives showed interesting antibacterial effects, with MIC values under 250 μM. These two Schiff base derivatives mainly exhibited a bacteriostatic effect against most of the studied bacterial strains. It is interesting to note that the same Schiff base presents the best activity in both biological evaluations. Full article
Show Figures

Scheme 1

Proceeding Paper
Designing a Phosphino-Thiosemicarbazone Ligand Capable of Stabilizing Coinage Metal Ions
Chem. Proc. 2022, 12(1), 44; https://doi.org/10.3390/ecsoc-26-13638 (registering DOI) - 16 Nov 2022
Viewed by 21
Abstract
Thiosemicarbazones are interesting organic skeletons due to their great coordinative versatility and their interesting biological and pharmacological properties, as well as their structural diversity. However, the isolation of their monovalent coinage metal complexes, such as Cu(I), Ag(I) and Au(I), is a partially studied [...] Read more.
Thiosemicarbazones are interesting organic skeletons due to their great coordinative versatility and their interesting biological and pharmacological properties, as well as their structural diversity. However, the isolation of their monovalent coinage metal complexes, such as Cu(I), Ag(I) and Au(I), is a partially studied field, since co-ligands with soft donor atoms such as phosphines are required. In this context, our research group has been studying a new family of ligands capable of stabilizing coinage complexes without the need for auxiliary co-ligands. To this end, it was decided to incorporate a phosphorus atom into the structure of a thiosemicarbazone kernel. This work presents the design, synthesis and structural characterization of a new phosphino-thiosemicarbazone ligand. Full article
Show Figures

Figure 1

Proceeding Paper
A New Hybrid Molecule Based on (5Z,9Z)-icosa-5,9-dienoic Acid and Monocarbonyl Derivatives of Curcuminoids
Chem. Proc. 2022, 12(1), 45; https://doi.org/10.3390/ecsoc-26-13636 (registering DOI) - 16 Nov 2022
Viewed by 5
Abstract
Efficient methods for the synthesis of previously undescribed hybrid compounds based on monocarbonyl derivatives of curcumin and 5Z,9Z-dienoic acid with yields of 58–66% are presented. The key monomer, (5Z,9Z)-icosa-5,9-dienoic acid, was prepared using the stereoselective [...] Read more.
Efficient methods for the synthesis of previously undescribed hybrid compounds based on monocarbonyl derivatives of curcumin and 5Z,9Z-dienoic acid with yields of 58–66% are presented. The key monomer, (5Z,9Z)-icosa-5,9-dienoic acid, was prepared using the stereoselective cross-cyclomagnesiation reaction of aliphatic and oxygen-containing 1,2-dienes catalyzed by Cp2TiCl2. Full article
Show Figures

Scheme 1

Proceeding Paper
Synthesis, Insecticidal Activity and Computational Studies of Eugenol-Based Insecticides
Chem. Proc. 2022, 12(1), 46; https://doi.org/10.3390/ecsoc-26-13649 - 16 Nov 2022
Viewed by 59
Abstract
Eugenol, a natural phenolic allyl benzene that has been used as an active lead compound showing significant biological activities, including insecticidal effects on a wide variety of domestic arthropod pests, was used as the main reagent in the present work. Ester eugenol derivatives [...] Read more.
Eugenol, a natural phenolic allyl benzene that has been used as an active lead compound showing significant biological activities, including insecticidal effects on a wide variety of domestic arthropod pests, was used as the main reagent in the present work. Ester eugenol derivatives were synthesized and evaluated for their insecticidal activities against the Spodoptera frugiperda cell line. Studies of structure-based inverted virtual screening were carried out in order to identify the potential targets associated with the obtained insecticidal activity. The results indicate that the insecticide activity observed is most likely a result of the interaction of these molecules with the odorant-binding proteins and/or with acetylcholinesterase. Full article
Show Figures

Figure 1

Proceeding Paper
Approach to the Synthesis of Five-Membered Organophosphorus Compounds via Alumoles and Alumolanes
Chem. Proc. 2022, 12(1), 47; https://doi.org/10.3390/ecsoc-26-13637 (registering DOI) - 16 Nov 2022
Viewed by 23
Abstract
This work summarizes the results of a new approach to the synthesis of previously undescribed, hard-to-obtain five-membered cyclic organophosphorus compounds: 3-alkyl(aryl)-substituted phospholanes, α,ω-bisphospholanes, polycyclic phospholanes, 4,5-dialkyl(diaryl)-disubstituted 2,3-dihydrophospholes, as well as their oxides and sulfides. Alumoles and alumolanes synthesized by the reaction of cycloalumination [...] Read more.
This work summarizes the results of a new approach to the synthesis of previously undescribed, hard-to-obtain five-membered cyclic organophosphorus compounds: 3-alkyl(aryl)-substituted phospholanes, α,ω-bisphospholanes, polycyclic phospholanes, 4,5-dialkyl(diaryl)-disubstituted 2,3-dihydrophospholes, as well as their oxides and sulfides. Alumoles and alumolanes synthesized by the reaction of cycloalumination of available unsaturated compounds (terminal alkenes, α,ω-alkadienes, norbornene derivatives, symmetrical internal alkynes) with Et3Al in the presence of a Cp2ZrCl2 catalyst were used as precursors. The substitution of aluminum atoms in cyclic organoaluminum compounds for phosphorus atoms takes place using alkyl(aryl)phosphorus (III) dichlorides. The developed one-pot method gives high yields of products under mild conditions. Full article
Show Figures

Scheme 1

Proceeding Paper
A Facile Method for Assessing the Change in Detonation Properties during Chemical Functionalization: The Case of NH2→NHNO2 and NH2→=N+=N Conversions
Chem. Proc. 2022, 12(1), 48; https://doi.org/10.3390/ecsoc-26-13566 (registering DOI) - 14 Nov 2022
Viewed by 8
Abstract
A simple and fast procedure for estimation of the effect of chemical functionalization on the change in detonation properties of energetic materials is reported. The procedure consists of two levels. Computations at Level 1 can be performed with a pocket calculator. At Level [...] Read more.
A simple and fast procedure for estimation of the effect of chemical functionalization on the change in detonation properties of energetic materials is reported. The procedure consists of two levels. Computations at Level 1 can be performed with a pocket calculator. At Level 2, quantum-chemical calculations are needed, but these include only three computational tasks: vacuum-isolated molecule relaxation (PBE/DND) → crystal structure prediction (COMPASSII) → crystal cell relaxation (PBE/DND). Thus, we have analyzed transformation of both aromatic and aliphatic amines into the corresponding nitramines and diazo compounds. The calculations at Level 1 indicated that both crystal density (dc) and solid-state enthalpy of formation (ΔHf) are always positive and increase detonation properties, while the calculations at Level 2 revealed the amines that are the most sensitive to such chemical transformation. Full article
Show Figures

Figure 1

Proceeding Paper
Cyclic 1H-Phospolane Oxides as a Potential Candidate for Cancer Therapy
Chem. Proc. 2022, 12(1), 49; https://doi.org/10.3390/ecsoc-26-13713 (registering DOI) - 18 Nov 2022
Viewed by 5
Abstract
Organophosphorus compounds have been investigated for agricultural and medicinal applications for decades, and a considerable number of phosphorus-containing drugs have achieved commercial success. A recent review by P. Finkbeiner et al. has shown that phosphine oxides and related phosphorus-containing functional groups are valuable [...] Read more.
Organophosphorus compounds have been investigated for agricultural and medicinal applications for decades, and a considerable number of phosphorus-containing drugs have achieved commercial success. A recent review by P. Finkbeiner et al. has shown that phosphine oxides and related phosphorus-containing functional groups are valuable polar structural elements and that they deserve to be considered as a routine part of every medicinal chemist’s toolbox. A new approach to the synthesis of previously hard-to-obtain 3-alkyl-1H-phospholanes oxides was developed by us. In order to assess the potential of five-membered cyclic organophosphorus compounds in cancer therapy, we carried out docking 3-buthyl-1H-phospholanes oxide and 2,3-dihydrophosphole in the binding site of 24 human proteins involved in oncogenesis processes. Proteins were selected using the PharmMapper in-house pharmacophore model database. The results are presented in the article. Full article
Show Figures

Figure 1

Proceeding Paper
Can the Antimicrobial Peptide Ctx(Ile21)-Ha-Ahx-Cys Grafted onto Nanochitosan Sensitize Extensively Drug-Resistant Mycobacterium tuberculosis?
Chem. Proc. 2022, 12(1), 51; https://doi.org/10.3390/ecsoc-26-13700 (registering DOI) - 18 Nov 2022
Viewed by 6
Abstract
The infectious agent Mycobacterium tuberculosis (MTB) has several defense and resistance mechanisms that must be eliminated. The treatment is prolonged, which in many cases generates susceptibility to microbial resistance. This research aimed to study whether the antimicrobial peptide Ctx(Ile21)-Ha-Ahx-Cys (Ctx-SH) functionalized [...] Read more.
The infectious agent Mycobacterium tuberculosis (MTB) has several defense and resistance mechanisms that must be eliminated. The treatment is prolonged, which in many cases generates susceptibility to microbial resistance. This research aimed to study whether the antimicrobial peptide Ctx(Ile21)-Ha-Ahx-Cys (Ctx-SH) functionalized in nanochitosan matrices could eliminate resistant MTB. For this, a nanosystem was developed with chitosan matrices previously modified with N-acetylcysteine functionalized to Ctx-SH. Modified chitosan nanoparticles (NPQ) were obtained by ionic gelation using sodium tripolyphosphate and loaded with rifampicin. Both chitosan and NPQ modifications were analyzed for physicochemical parameters by Fourier/Raman transform infrared spectroscopy and Zeta potential. Antimicrobial activity was performed in a level 3 biosafety laboratory with strains H37Rv (standard) and CF169 (extensively drug-resistant, XDR) incubated in 7H9 broth supplemented with oleic acid, albumin, dextrose, and catalase at 37 °C and 5% CO2 and read using fluorescence with 0.01% resazurin after 7 days. Insertion and mapping of NPQ into macrophages were assessed using a confocal microscope after 24 h with NPQ conjugated to fluorescein isothiocyanate. Preliminary results show that the spectroscopies corroborate the hypothesis of the functionalization of the Ctx-SH peptide to the chitosan-N-acetylcysteine system because, when comparing the three spectroscopies, a gradual increase in the intensity of several bands and the formation of captive disulfide are observed, and the Zeta potential (+30 mV) confirmed high application stability. Bacterial inhibition studies revealed that rifampicin-loaded antimicrobial peptide-conjugated chitosan nanoparticles have better activity than rifampicin alone against CF169, with a minimum inhibitory concentration of <0.977 µg/mL, similar to the standard strain. In addition, it was shown that NPQ would be able to enter the macrophage without causing toxicity and thus take better advantage of the activity of rifampicin. Finally, it is possible to verify that the nanobioconjugation of the Ctx-SH-N-acetylcysteine-chitosan compound is capable of enhancing the activity of obsolete drugs and/or sensitizing XDR bacteria. Full article
Show Figures

Figure 1

Back to TopTop