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1 pages, 188 KiB

Open AccessAbstract

Quantitative Analysis of Total Phenolic and Flavonoid Contents from Stachys mouretii Leaf Extracts

by Abdelmoughite Ouakil, Soumaya El Ismaili, Ouafaa El Mahdi, Amal Maurady, Brahim El Bali and Mohammed Lachkar

Chem. Proc. 2022, 8(1), 21; https://doi.org/10.3390/ecsoc-25-11802 - 14 Nov 2021

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Abstract

Stachys mouretii leaf extracts were analyzed for total phenolic and flavonoid contents. These components are responsible for antioxidant activity. The plant material was collected in April 2018 at the forest of Talasemtane in the region of Ouazzane, Morocco. Dried and crushed leaves were [...] Read more.

Stachys mouretii leaf extracts were analyzed for total phenolic and flavonoid contents. These components are responsible for antioxidant activity. The plant material was collected in April 2018 at the forest of Talasemtane in the region of Ouazzane, Morocco. Dried and crushed leaves were subjected to sequential extraction with hexane, ethyl acetate, and methanol in order of increasing polarity. The amount of total phenolic and flavonoid content were determined with Folin–Ciocalteu and aluminum chloride (AlCl₃) reagents, respectively. For the total phenolic content, gallic acid was used as a standard compound and the results were expressed as µg/mL gallic acid equivalent (GAE), while for the total flavonoids, quercetin was used as a standard compound and the results were expressed as mg/mL quercetin equivalent (QE). The total phenolic content of Stachys mouretii leaf extracts varied from 14.13 to 26.91 µg/mL GAE and the total flavonoid content ranges from 0.04 to 0.08 mg/mL QE. The maximum phenolic and flavonoid contents were found in the ethyl acetate extract. The findings suggested that phytochemicals present in Stachys mouretii are potentially beneficial as therapeutic and antioxidative agents in pharmaceuticals, foods and other related industries. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 2176 KiB

Open AccessProceeding Paper

Multicomponent Reactions of Isocyanides for the Preparation of Low Molecular Weight Gelators: Preliminary Studies

by José L. Ramiro, Carlos F. Marcos and Ana G. Neo

Chem. Proc. 2022, 8(1), 1; https://doi.org/10.3390/ecsoc-25-11668 - 13 Nov 2021

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Abstract

Low molecular weight gelators, LMWGs, are small molecules that can self-associate in organic solvents or in water to form fibrous supramolecular architectures and three-dimensional networks that present important applications in several fields. Although various strategies are known for the synthesis of these type [...] Read more.

Low molecular weight gelators, LMWGs, are small molecules that can self-associate in organic solvents or in water to form fibrous supramolecular architectures and three-dimensional networks that present important applications in several fields. Although various strategies are known for the synthesis of these type of compounds, these are commonly hampered by the use of long multistep processes that include the protection and deprotection of functional groups. Therefore, it is essential to find direct and robust reactions that allow introducing the complexity and structural diversity necessary to obtain tailor-made functional materials in a simple and efficient way. A promising approach to this end is the use of multicomponent reactions. Based on our experience in this field, we report our studies aimed at the use of multicomponent reactions of isocyanides to prepare LMWGs. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 653 KiB

Open AccessProceeding Paper

Development and Optimization of the Multi-Gram Synthesis of the Antiviral 18-(Phthalimide-2-yl)ferruginol

by Francisco Javier Miquel-Leal, Natalia González-Zapata, Orlando José Jimenez-Jarava, Yaneth M. Brand, Liliana Betancur-Galvis, Maria Luisa Marín and Miguel A. González-Cardenete

Chem. Proc. 2022, 8(1), 2; https://doi.org/10.3390/ecsoc-25-11667 - 13 Nov 2021

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Abstract

Virus-induced diseases are very common in our society, and we continuously need new treatments for these challenging infections. We discovered by serendipity some years ago that the molecule 18-(Phthalimide-2-yl)ferruginol, an analogue of the natural diterpenoid (+)-ferruginol, a pharmacologically active molecule, was able to [...] Read more.

Virus-induced diseases are very common in our society, and we continuously need new treatments for these challenging infections. We discovered by serendipity some years ago that the molecule 18-(Phthalimide-2-yl)ferruginol, an analogue of the natural diterpenoid (+)-ferruginol, a pharmacologically active molecule, was able to inhibit the spread of dengue virus type-2 (DENV-2) and human herpes virus 1 and 2 (HHV-1 and HHV-2). During the development and further study of the above-mentioned analogue, we required the scaling-up of the semisynthesis of the target molecule. The synthesis was already reported by Waldvogel and co-workers in 2007, starting from the commercially available ca. 60% (+)-dehydroabietylamine. In this communication, we describe the several issues that we faced and propose an optimized experimental procedure in order to obtain this broad-spectrum antiviral, which we found is even active against several strains of Zika virus. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1390 KiB

Open AccessProceeding Paper

Influence of At-Bridge Nitro Groups on the Photophysics and Chiroptics of helicoBODIPYs: A Step Forward towards the Development of New Chiroptical Sensors

by César Ray, Carolina Díaz-Norambuena, Christopher Schad, Florencio Moreno, Antonia R. Agarrabeitia, María J. Ortiz, Teresa Arbeloa, Jorge Bañuelos, Beatriz L. Maroto and Santiago de la Moya

Chem. Proc. 2022, 8(1), 3; https://doi.org/10.3390/ecsoc-25-11701 - 14 Nov 2021

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Abstract

A new helicoBODIPY (bisBODIPY with helical chirality) with nitro groups at the chiral bridge has been synthesized as a model to study the influence of the at-bridge substitution on the photophysics and chiroptics of the helicoBODIPY. This preliminary study reveals that at-bridge substitution [...] Read more.

A new helicoBODIPY (bisBODIPY with helical chirality) with nitro groups at the chiral bridge has been synthesized as a model to study the influence of the at-bridge substitution on the photophysics and chiroptics of the helicoBODIPY. This preliminary study reveals that at-bridge substitution can be a strategy for the development of chiroptical sensors based on helicoBODIPYs. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1636 KiB

Open AccessProceeding Paper

Synthesis of Heterocycles and Nucleosides Forming Higher—Order Structures

by Zoltán Váradi, Gábor Paragi, Zoltán Kupihár, Zoltán Kele and Lajos Kovács

Chem. Proc. 2022, 8(1), 4; https://doi.org/10.3390/ecsoc-25-11705 - 14 Nov 2021

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Abstract

Nucleic acid analogues play a multifaceted role in biology and materials science. Our efforts towards unveiling these roles led to xanthine derivatives that form higher–order structures with quadruplex-forming abilities. In this paper we present further modifications of the xanthine core resulting into 9-deaza [...] Read more.

Nucleic acid analogues play a multifaceted role in biology and materials science. Our efforts towards unveiling these roles led to xanthine derivatives that form higher–order structures with quadruplex-forming abilities. In this paper we present further modifications of the xanthine core resulting into 9-deaza and 8-aza-9-deaza heterocycles (pyrrolo[3,2-d]pyrimidines and pyrazolo[4,3-d]pyrimidines, respectively) that form tetrads and other higher–order structures. Additionally, the ring contraction of 5-fluoro-2′,3′-O-isopropylideneuridine gave rise to the formation of an imidazolidine-4-carboxylic acid nucleoside derivative. Our computational predictions forecasted that the latter derivative will form stable triads. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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13 pages, 1721 KiB

Open AccessProceeding Paper

An In Silico Approach for Potential Natural Compounds as Inhibitors of Protein CDK1/Cks2

by Abu Saim Mohammad Saikat

Chem. Proc. 2022, 8(1), 5; https://doi.org/10.3390/ecsoc-25-11721 - 14 Nov 2021

Cited by 6 | Viewed by 1674

Abstract

CDKs are pivotal mediators essential for the cellular cycle progression. CDKs have relatively constant levels, and their activity is regulated by cyclins, proteins whose concentrations fluctuate during each cell cycle. Consequently, more CDK family members were found that occupy crucial functions in a [...] Read more.

CDKs are pivotal mediators essential for the cellular cycle progression. CDKs have relatively constant levels, and their activity is regulated by cyclins, proteins whose concentrations fluctuate during each cell cycle. Consequently, more CDK family members were found that occupy crucial functions in a variety of processes. Moreover, CKS2 is a member of the CDK family, which has been implicated in several malignancies as an oncogene. Additionally, CKS2 is engaged in many biological processes, including the cell cycle transition. CKS2 may act synergistically to promote embryonic development and somatic cell division. Current CDK2 drugs, however, also suppress CDK1, posing a toxicity risk. Investigators demonstrated that the potential conformational maps of cyclin-free CDK1 and CDK2 exhibit slight but substantial differences. The CDK1 unique characteristics may be used to distinguish it from other CDKs in prospective cancer treatment design. Computational-based in silico docking investigations were performed to uncover promising CDK1/Cks2 (6GU7) inhibitors utilizing the Maestro tool. Curcumin, quercetin, withanolide, and genistein were selected against the protein CDK1/Cks2 for protein–ligand XP docking. The physicochemical, lipophilicity, water-solubility, pharmacokinetics, drug-likeness, medicinal chemistry, and toxicological properties were analyzed using SwissADME and pkCSM of the selected ligands. Curcumin exerted an excellent docking score complexed with 6GU7 compared to other ligands. The revealed hit may be a potent inhibitor of 6GU7. However, it will require to be assessed extensively in vivo and in vitro experimental models. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 376 KiB

Open AccessProceeding Paper

Targeted Synthesis and Antitumor Activity In Vitro Macrodiolides Containing 1Z,5Z-Diene and 1,3-Diyne Moieties

by Ilgiz Islamov, Adelya Yusupova, Lilya U. Dzhemileva and Usein Dzhemilev

Chem. Proc. 2022, 8(1), 6; https://doi.org/10.3390/ecsoc-25-11704 - 14 Nov 2021

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Abstract

Efficient methods have been developed for synthesizing previously unknown macrodiolides incorporating 1Z,5Z-diene and 1,3-diyne moieties in 54–84% yields and with >98% stereoselectivity by means of the intermolecular cyclocondesation of (7Z,11Z)-octadeca-7,11-dienedioic acid with α,ω-diols catalyzed by [...] Read more.

Efficient methods have been developed for synthesizing previously unknown macrodiolides incorporating 1Z,5Z-diene and 1,3-diyne moieties in 54–84% yields and with >98% stereoselectivity by means of the intermolecular cyclocondesation of (7Z,11Z)-octadeca-7,11-dienedioic acid with α,ω-diols catalyzed by hafnium triflate Hf(OTf)₄ as well as via the oxidative coupling of α,ω-diynes obtained by the esterification of (7Z,11Z)-octadeca-7,11-dienedioic acid with alkynols. The synthesized macrodiolides exhibit cytotoxic activity toward the Jurkat, K562, U937, HL-60, HeLa, and Hek293 cell lines in vitro. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1165 KiB

Open AccessProceeding Paper

Synthesis of 4-Arylallylidenepyrazolone Derivatives

by Esteban Aguilar-Llanos, Juan Carlos Romero-Benavides and Jorge Heredia-Moya

Chem. Proc. 2022, 8(1), 7; https://doi.org/10.3390/ecsoc-25-11714 - 14 Nov 2021

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Abstract

Pyrazoles and their derivatives have attracted particular attention because they have a wide variety of biological activities, and recently, we found that 4,4’-(arylmethylene)-bis-(1-phenyl-3-methyl-1H-pyrazole-5-ols) have good leishmanicidal activity against promastigotes of Leishmania mexicana. 4-Arylidenepyrazolone derivatives also have antiparasitic activity and are intermediates [...] Read more.

Pyrazoles and their derivatives have attracted particular attention because they have a wide variety of biological activities, and recently, we found that 4,4’-(arylmethylene)-bis-(1-phenyl-3-methyl-1H-pyrazole-5-ols) have good leishmanicidal activity against promastigotes of Leishmania mexicana. 4-Arylidenepyrazolone derivatives also have antiparasitic activity and are intermediates in the synthesis of these bispirazoles that are formed by the equimolar reaction of 3-methyl-1-phenyl-2-pyrazoline-5-one with aromatic aldehydes. In order to obtain new compounds with potential leishmanicidal activity, we attempted to synthesize several 4-arylallylidenepyrazolone derivatives through the reaction of pyrazol-3-one with different cinnamaldehydes. We report here the study of the synthesis of some 4-arylallylidenepyrazolone derivatives from the reaction between 5-methyl-2-phenyl-2,4-dihydro-3H-pyrazol-3-one and 4-nitrocinnamaldehyde. We found that L-proline and FeCl₃ were the best catalysts, and we also observed a solvent effect in the reaction. Our preliminary results indicate that aprotic solvents favor the formation of the 2Z isomer instead of the 2E isomer. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 502 KiB

Open AccessProceeding Paper

Evaluation of the Recovery of Furfural from Wood Scraps

by Mariana Celman, Leandro Gutierrez, Carla Ormachea and Cristián Ferretti

Chem. Proc. 2022, 8(1), 8; https://doi.org/10.3390/ecsoc-25-11715 - 14 Nov 2021

Cited by 1 | Viewed by 1637

Abstract

2-furfuraldehyde, commonly known as furfural, is a product of the hydrolysis and dehydration of pentose carbohydrates contained in lignocellulosic. Furfural is currently a commodity chemical, identified as one of the most promising chemical platforms directly derived from biomass, to produce chemicals, biofuels, and [...] Read more.

2-furfuraldehyde, commonly known as furfural, is a product of the hydrolysis and dehydration of pentose carbohydrates contained in lignocellulosic. Furfural is currently a commodity chemical, identified as one of the most promising chemical platforms directly derived from biomass, to produce chemicals, biofuels, and additives. Wood scraps are a good source of natural pentoses that contains up to 25%. Taking this into account, the goal of the research was to evaluate the recovery of furfural from wood scraps. The process of recovery of furfural was carried out by acid-catalyzed pentoses dehydration, associated with a hydrodistillation. As a catalyst, we used a solution of hydrochloric acid of 10% wt. The physicochemical analysis of the samples obtained allowed us to characterize and evaluate the recovery process. The results showed that under the experimental conditions evaluated, the degree of recovery of furfural was about 5%. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 829 KiB

Open AccessProceeding Paper

Synthesis of Functionalized Pararosaniline over Mild Conditions

by Leandro Gutierrez, Alejandro Vallejo Orrego and Cristián A. Ferretti

Chem. Proc. 2022, 8(1), 9; https://doi.org/10.3390/ecsoc-25-11712 - 14 Nov 2021

Cited by 1 | Viewed by 1582

Abstract

Dyes and pigments have many applications, and their growing development is driven by their increased use. As a contribution to this topic, in this work, the synthesis of functionalized pararosaniline was evaluated with the aim to obtain an amphiphilic dye. Pararosaniline is a [...] Read more.

Dyes and pigments have many applications, and their growing development is driven by their increased use. As a contribution to this topic, in this work, the synthesis of functionalized pararosaniline was evaluated with the aim to obtain an amphiphilic dye. Pararosaniline is a dye highly soluble in water and polar solvents, presenting three amino groups in its structure. We realized that the functionalization of pararosaniline by direct coupling of amino groups with halogenated fatty acids leads to amides derived from fatty acid. In the synthesis, fatty acid chloride from sunflower oil and basic catalysts were used. Over a single step one-pot procedure carried out at room temperature in moderate reaction time, a new functionalized pararosaniline was synthesized. The results showed that after derivatization with chloride of fatty acids, the dye exhibits solubility both in water and in non-polar systems with different color intensities. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 2605 KiB

Open AccessProceeding Paper

In Silico Evaluation of Antioxidant Properties of Cinnamaldehyde Phenylhydrazone

by Carla Ormachea and Cristián A. Ferretti

Chem. Proc. 2022, 8(1), 10; https://doi.org/10.3390/ecsoc-25-11711 - 14 Nov 2021

Cited by 1 | Viewed by 1135

Abstract

Hydrazone-type Schiff bases derived from natural compounds have been demonstrated to be effective and versatile antioxidants. In particular, the interest of this work is to analyze the antioxidant activity of cinnamaldehyde phenylhydrazone (CPH), an effective antioxidant synthesized by our group, through theoretical calculations. [...] Read more.

Hydrazone-type Schiff bases derived from natural compounds have been demonstrated to be effective and versatile antioxidants. In particular, the interest of this work is to analyze the antioxidant activity of cinnamaldehyde phenylhydrazone (CPH), an effective antioxidant synthesized by our group, through theoretical calculations. Considering that the enzymes cytochrome P450 (CP450) and NADPH oxidase (NO) are associated with the oxidative stress process, we chose these enzymes to evaluate their interaction with the antioxidant CPH. The interactions were analyzed by coupling studies performed with the SwissDock server. Considering the parameters of the scoring function based on the energy of the system, the best protein–ligand binding geometries were obtained, and the interaction distances between the CPH enzymes were studied. Taking into account the information from all the data obtained, it could be concluded that CPH has strong interactions with enzymatic substrates due to electrostatic interactions with amino acid residues present in segments corresponding to hydrophobic domains. These results attest to the significant antioxidant capacity of CPH observed in experimental antioxidant tests. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1400 KiB

Open AccessProceeding Paper

Reaction of Some Substituted (Un)Substituted Isatins with 1,ω-Alkanes and Their Products with Sodium Azide

by Nguyen Minh Tri, Vu Ngoc Toan, Hoang Mai Linh, Ngo Thi Ngoc Mai, Tran Thi-Hai-Yen, Ngo Thi Thuy, Nguyen Thi Thuy Huong, Pham Thi Thuy Van, Tran Thi Hai Yen, Nguyen Thi Kim Giang, Hoang Thi Kim Van and Nguyen Dinh Thanh

Chem. Proc. 2022, 8(1), 11; https://doi.org/10.3390/ecsoc-25-11716 - 14 Nov 2021

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Abstract

Azide derivatives of isatins were the initial materials needed for click chemistry, so as to form 1,2,3-triazoles in order to synthesize the hybrid compounds of 1,2,3-triazole–isatin with monosaccharide moieties. The required substituted isatins were prepared according to the Sandmeyer method from corresponding substituted [...] Read more.

Azide derivatives of isatins were the initial materials needed for click chemistry, so as to form 1,2,3-triazoles in order to synthesize the hybrid compounds of 1,2,3-triazole–isatin with monosaccharide moieties. The required substituted isatins were prepared according to the Sandmeyer method from corresponding substituted anilines. N-(ω-bromoalkyl) isatins were prepared through the nucleophilic reaction, S_N2, of (un)substituted isatins with appropriate dibromoalkanes. Some ω-azidoalkylisatins were synthesized by the reaction of corresponding ω-bromoalkylisatins with sodium azide. The reactions were performed in dry DMF as solvents in the presence of K₂CO₃ as the base and KI as the promoting agent. The product yields reached 30–85%. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 702 KiB

Open AccessProceeding Paper

Synthesis and Antimicrobial Screening of Some New Thiazole Substituted 1,3,4-Oxadiazole Derivatives

by Siddhant V. Kokate and Sachin V. Patil

Chem. Proc. 2022, 8(1), 12; https://doi.org/10.3390/ecsoc-25-11662 - 15 Nov 2021

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Abstract

In the present work, the synthesis and antimicrobial activity of new thiazole substituted 1,3,4-oxadiazole derivatives was achieved. The reaction of different thioamides with ethyl 4-chloro-3-oxobutanoate (4-chloro ethyl acetoacetate) provided ethyl 2-(2-arylthiazol-4yl)acetate, which on subsequent reaction with hydrazine hydrate in absolute ethanol afforded 2-(2-arylthiazol-4-yl)acetohydrazide. [...] Read more.

In the present work, the synthesis and antimicrobial activity of new thiazole substituted 1,3,4-oxadiazole derivatives was achieved. The reaction of different thioamides with ethyl 4-chloro-3-oxobutanoate (4-chloro ethyl acetoacetate) provided ethyl 2-(2-arylthiazol-4yl)acetate, which on subsequent reaction with hydrazine hydrate in absolute ethanol afforded 2-(2-arylthiazol-4-yl)acetohydrazide. 2-(2-arylthiazol-4-yl)acetohydrazide, on reaction with CS₂ and KOH in aqueous ethanol, cyclized to form 5-((2-arylthiazol-4-yl)methyl)-1,3,4-oxadiazole-2-thiol. Finally, 5-((2-arylthiazol-4-yl)methyl)-1,3,4-oxadiazole-2-thiol was further treated with α-halo ketones at room temperature to achieve the target compounds. Most of the compounds showed good antibacterial activity, as well as antifungal activity. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 348 KiB

Open AccessProceeding Paper

In-Silico Studies toward the Improvement of the Antibacterial Activity of Pristinamycin IIB

by Assia Chebieb, Chewki Ziani-Cherif and Khadidja Bellifa

Chem. Proc. 2022, 8(1), 13; https://doi.org/10.3390/ecsoc-25-11703 - 14 Nov 2021

Viewed by 895

Abstract

Pristinamycin IIB (PIIB) is a potent antibiotic with limited use, due to some structural problems and also due to the bacterial resistance exhibited toward the antibiotic. A thorough study led to the design of novel analogues of PIIB, based on the introduction of [...] Read more.

Pristinamycin IIB (PIIB) is a potent antibiotic with limited use, due to some structural problems and also due to the bacterial resistance exhibited toward the antibiotic. A thorough study led to the design of novel analogues of PIIB, based on the introduction of a difluorostatone moiety. Herein, we describe the initial in silico studies toward these novel analogues using ADMET modeling of predictive models in order to compute the physicochemistry and estimate the pharmacokinetics, drug-likeness and medicinal chemistry friendliness of these newly designed analogues. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 4122 KiB

Open AccessProceeding Paper

Study on the Effect of Applying Benzimidazole–Ethanol Solution as a Film–Forming Corrosion Inhibitor on the Surface of Aluminium Alloy 2024-T3

by Magdi Hassn Mussa, Sarra Takita, Farah Deeba Zahoor, Oliver Lewis and Nicholas Farmilo

Chem. Proc. 2022, 8(1), 14; https://doi.org/10.3390/ecsoc-25-11635 - 12 Nov 2021

Viewed by 1254

Abstract

The Al-Cu-Mg light alloys’ storage characteristics are such that their use for building structures, marine offshore applications, and aeroplane components, with excellent strength/weight ratios, would not be possible without adherent anticorrosion preservation. Many techniques and strategies are still being used to treat the [...] Read more.

The Al-Cu-Mg light alloys’ storage characteristics are such that their use for building structures, marine offshore applications, and aeroplane components, with excellent strength/weight ratios, would not be possible without adherent anticorrosion preservation. Many techniques and strategies are still being used to treat the surfaces, such as cladding, anodising, and greasing. However, due to their costly and time-consuming nature, these techniques are considered complicated. Therefore, volatile organic inhibitor components are now being used effectively. Benzimidazole (BZI) and its derivatives are one of these film-forming chemicals used on copper and steel, directly or as injectables, combined with other carriers, such as fatty acids or dissolvable hydrocarbons, with highly efficient corrosion protection. Therefore, this paper will investigate the enhancement of the corrosion protection afforded by direct spraying of BZI solution on the surface of aluminium alloy AA 2024-T3 The corrosion protection performance results from the high electronegativity of BZI as a film-forming inhibitor, which will be adsorbed on the metallic surface, as it may emulate active protection. The corrosion protection properties of the BZI film-forming coating were preliminarily studied with 3.5% NaCl by using electrochemical impedance testing and simulations. The surface chemical adsorption confirmation was carried out by infrared spectroscopy (ATR-FTIR), supported by analysing the morphology of the surface before and after the immersion testing by using scanning electron microscopy (SEM) real-time imaging within one week of immersion. The benzimidazole film-forming coating exhibited good anticorrosion properties, providing an adherent protection film on AA 2024-T3 samples comparing with bare cladded AA 2024-T3, with a cost-effective and easy application process. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 2155 KiB

Open AccessProceeding Paper

Synthesis, Characterization, and Preliminary Chemosensory Ability of a Novel 2,4,5-Tri(Hetero)Arylimidazole Based on an 8-Hydroxy-Quinoline Group

by Odília M. P. F. Luís, Nuna L. P. Ramos, Susana P. G. Costa and Maria Manuela M. Raposo

Chem. Proc. 2022, 8(1), 15; https://doi.org/10.3390/ecsoc-25-11748 - 14 Nov 2021

Viewed by 887

Abstract

2,4,5-Trisubstituted imidazole derivatives with heteroaromatic groups are versatile heterocyclic compounds exhibiting a wide range of biological activities, as well as very interesting thermal, optical, electronic, and redox properties. In recent years, this type of imidazole derivatives has been explored as colorimetric and fluorimetric [...] Read more.

2,4,5-Trisubstituted imidazole derivatives with heteroaromatic groups are versatile heterocyclic compounds exhibiting a wide range of biological activities, as well as very interesting thermal, optical, electronic, and redox properties. In recent years, this type of imidazole derivatives has been explored as colorimetric and fluorimetric chemosensors due to their ability to coordinate with ions of biological and environmental relevance. In order to continue the work developed by the research group, we report the synthesis and characterization using usual spectroscopic techniques (NMR, absorption and emission spectroscopies) of a new imidazole derivative, substituted at position 2 of the imidazole with an 8-hydroxy-quinoline group. Furthermore, to complement the characterization of the synthesized imidazole, a preliminary study as an optical chemosensor was carried out in acetonitrile in the presence of ions with biological, medicinal, and environmental relevance. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 803 KiB

Open AccessProceeding Paper

Design, Synthesis and Structural Characterization of a Novel Asymmetric Hydrazone-Thiosemicarbazone Ligand with the Aim of Obtaining Interesting Metallosupramolecular Architectures

by Sandra Fernández-Fariña, Isabel Velo-Heleno, Miguel Martínez-Calvo, Ana M. González-Noya and Rosa Pedrido

Chem. Proc. 2022, 8(1), 16; https://doi.org/10.3390/ecsoc-25-11738 - 14 Nov 2021

Viewed by 1108

Abstract

The asymmetric hydrazone-thiosemicarbazone ligand H₂L was synthesized in two stages by means of a double-condensation reaction. The potentially dianionic and pentadentate [N₃SO] organic ligand H₂L possesses two flexible bidentate [NS/NO] domains separated by a pyridine spacer, which [...] Read more.

The asymmetric hydrazone-thiosemicarbazone ligand H₂L was synthesized in two stages by means of a double-condensation reaction. The potentially dianionic and pentadentate [N₃SO] organic ligand H₂L possesses two flexible bidentate [NS/NO] domains separated by a pyridine spacer, which could stabilize a wide variety of metal ions, giving rise to different supramolecular architectures. This ligand was fully characterized by different techniques such as elemental analysis, infrared spectroscopy, mass spectrometry and ¹H/¹³C NMR, confirming that it was obtained with high purity. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 902 KiB

Open AccessProceeding Paper

Benzene-1,3,5-tricarboxylic Acid-Functionalized Cherry Gum as a Novel and Recoverable Nanocatalyst for Efficient Synthesis of 1,4-polyhydroquinoline Derivatives

by Hossein Ghafuri, Behnaz Abbasi, Nastaran Ghanbari, Yegane Rostami, Zeinab Tajik and Mahdi Akhgari

Chem. Proc. 2022, 8(1), 17; https://doi.org/10.3390/ecsoc-25-11717 - 14 Nov 2021

Cited by 1 | Viewed by 1284

Abstract

In this study, Benzene-1,3,5-tricarboxylic acid (BTA)-functionalized gum (Cherry gum) (gum-Pr-BTA) was prepared as a novel nanocatalyst. This novel nanocatalyst was used for the expeditious and efficient synthesis of 1,4-polyhydroquinoline derivatives, as an important pharmaceutical scaffold, in ethanol reflux conditions. This method has several [...] Read more.

In this study, Benzene-1,3,5-tricarboxylic acid (BTA)-functionalized gum (Cherry gum) (gum-Pr-BTA) was prepared as a novel nanocatalyst. This novel nanocatalyst was used for the expeditious and efficient synthesis of 1,4-polyhydroquinoline derivatives, as an important pharmaceutical scaffold, in ethanol reflux conditions. This method has several advantages such as high yields, low catalyst loading, short reaction times, and a simple workup and could be used for up to five reaction cycles without a noticeable decrease in catalytic activity. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1285 KiB

Open AccessProceeding Paper

Gum-Supported Melamine: A Recyclable Reagent for Selective and Metal-Free Oxidation of Benzyl Alcohols

by Hossein Ghafuri, Yegane Rostami, Nastaran Ghanbari, Behnaz Abbasi, Zeinab Tajik and Nasim Amiri Ramsheh

Chem. Proc. 2022, 8(1), 18; https://doi.org/10.3390/ecsoc-25-11718 - 14 Nov 2021

Viewed by 1182

Abstract

Here, novel melamine functionalized gum (gum@Melamine@Cu(II)) is synthesized and its catalytic performance is investigated in the oxidation of benzyl alcohols. The gum@Melamine was prepared through the grafting of 3-chloropropyltrimethoxysilane onto gum, followed by treatment with melamine. The synthesized gum@Melamine@Cu(II) was used to achieve [...] Read more.

Here, novel melamine functionalized gum (gum@Melamine@Cu(II)) is synthesized and its catalytic performance is investigated in the oxidation of benzyl alcohols. The gum@Melamine was prepared through the grafting of 3-chloropropyltrimethoxysilane onto gum, followed by treatment with melamine. The synthesized gum@Melamine@Cu(II) was used to achieve an effective and selective method for the oxidation of different alcohols. All substituted benzyl alcohols were oxidized in good yields under mild conditions at room temperature. This gum@Melamine@Cu(II) has great stability and could be recycled five times without noteworthy loss of activity. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 954 KiB

Open AccessProceeding Paper

Study on the Effect of the Ligand Structure in Palladium Organometallic Catalysts in the Suzuki–Miyaura Cross-Coupling Reaction

by Paula Munín-Cruz, Marcos Rúa-Sueiro, Juan Manuel Ortigueira, María Teresa Pereira and José Manuel Vila

Chem. Proc. 2022, 8(1), 19; https://doi.org/10.3390/ecsoc-25-11730 - 14 Nov 2021

Viewed by 839

Abstract

In this communication, we present the results obtained using a family of cyclometallated palladium compounds as catalysts for the Suzuki–Miyaura cross-coupling reaction between an aryl halide and phenylboronic acid. We have studied the structural factors that enhance the efficiency of the catalyst for [...] Read more.

In this communication, we present the results obtained using a family of cyclometallated palladium compounds as catalysts for the Suzuki–Miyaura cross-coupling reaction between an aryl halide and phenylboronic acid. We have studied the structural factors that enhance the efficiency of the catalyst for this process through the synthesis of a library of analogous compounds containing thiosemicarbazone ligands with substituted rings and ferrocene diphosphine (dppf). We found that the best conversion rates are obtained with ligands bearing methoxy-disubstituted aromatic rings, and that the process performance is improved when R² is a methyl group bound to the thioamidic nitrogen. These results lay the foundations for the design and development of novel and more efficient palladium catalysts based on thiosemicarbazones. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1438 KiB

Open AccessProceeding Paper

Synthesis, Characterization and Evaluation of a Carbazolyl-BODIPY as a Fluorimetric Chemosensor for F^-

by Sónia C. S. Pinto, Raquel C. R. Gonçalves, Susana P. G. Costa and Maria Manuela M. Raposo

Chem. Proc. 2022, 8(1), 20; https://doi.org/10.3390/ecsoc-25-11752 - 14 Nov 2021

Cited by 4 | Viewed by 1083

Abstract

BODIPY dyes have received great attention in the last few years as optical chemosensors since they can recognize metal ions in solutions through optical signals (colorimetric and/or fluorimetric). In this context, our research group reports the synthesis of a carbazolyl-BODIPY derivative and its [...] Read more.

BODIPY dyes have received great attention in the last few years as optical chemosensors since they can recognize metal ions in solutions through optical signals (colorimetric and/or fluorimetric). In this context, our research group reports the synthesis of a carbazolyl-BODIPY derivative and its respective characterization by ¹H NMR spectroscopy and mass spectrometry. Furthermore, a preliminary study of the chemosensory capacity of this BODIPY derivative was carried out in acetonitrile solution in the presence of several anions and a highly selective fluorimetric response was obtained for F^-. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1311 KiB

Open AccessProceeding Paper

Multicomponent Crystalline Solid Forms of Pyridinecarboxamides and DL-2-Hydroxy-2-phenylacetic Acid

by Alfonso Castiñeiras, Isabel García-Santos and Rocío Torres-Iglesias

Chem. Proc. 2022, 8(1), 22; https://doi.org/10.3390/ecsoc-25-11729 - 14 Nov 2021

Viewed by 1101

Abstract

We have prepared co-crystals of racemic DL-2-Hydroxy-2-phenylacetic acid (DL-Mandelic acid, DL-H₂ma) with achiral 2-Pyridinecarboxamide (picolinamide, pic), 3-Pyridinecarboxamide (nicotinamide, nam), and 4-Pyridinecarboxamide (isonicotinamide, inam); they have been characterized by elemental analysis, single crystal and powder X-ray, IR spectroscopy [...] Read more.

We have prepared co-crystals of racemic DL-2-Hydroxy-2-phenylacetic acid (DL-Mandelic acid, DL-H₂ma) with achiral 2-Pyridinecarboxamide (picolinamide, pic), 3-Pyridinecarboxamide (nicotinamide, nam), and 4-Pyridinecarboxamide (isonicotinamide, inam); they have been characterized by elemental analysis, single crystal and powder X-ray, IR spectroscopy and ¹H and ¹³C NMR. The crystal packing is stabilized primarily by hydrogen bonding and, in some cases, through π–π stacking interactions. The analysis of crystal structures reveals the existence of the characteristic heterosynthons with the binding motif

R_{2}^{2} (8)

(primary amide-carboxilic acid) between pyridinecarboxamide molecules and the acid. Other synthons involve hydrogen bonds such as (carboxyl)O-H···N(pyridine) and (hydroxyl)O-H···N(pyridine). Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1424 KiB

Open AccessProceeding Paper

Efficient and Green Synthesis of Acridinedione Derivatives Using Highly Fe₃O₄@Polyaniline-SO₃H as Efficient Heterogeneous Catalyst

by Hossein Ghafuri, Shahram Moradi, Nastaran Ghanbari, Haniyeh Dogari and Mostafa Ghafori

Chem. Proc. 2022, 8(1), 23; https://doi.org/10.3390/ecsoc-25-11719 - 14 Nov 2021

Cited by 1 | Viewed by 1660

Abstract

In the present investigation, an efficient heterogeneous catalyst system made of a polyaniline-derived polymer (Poly [anthranilic acid]-[N-(1′,3′-phenylenediamino) −3-butane sulfonate]) and iron oxide nanoparticles (Fe₃O₄ NPs) is presented. Firstly, this novel catalytic system (Fe₃O₄@Polyaniline-SO₃H) has [...] Read more.

In the present investigation, an efficient heterogeneous catalyst system made of a polyaniline-derived polymer (Poly [anthranilic acid]-[N-(1′,3′-phenylenediamino) −3-butane sulfonate]) and iron oxide nanoparticles (Fe₃O₄ NPs) is presented. Firstly, this novel catalytic system (Fe₃O₄@Polyaniline-SO₃H) has been fabricated via a convenience method and magnetized via an in situ process. The as-prepared solid acid catalyst was also carefully analyzed by Fourier transfer infrared spectroscopy (FTIR) and energy-dispersive X-ray spectroscopy (EDX). It has been suitably applied for the one-pot multicomponent synthesis of acridinediones as an important class of heterocyclic compounds. The first and foremost advantage of this catalytic system is that the (Fe₃O₄@Polyaniline-SO₃H) is magnetically separated from the reaction mixture through their high paramagnetic behavior. The main attractive characteristics of the presented green protocol are very short reaction times, excellent yields, and the avoidance of hazardous or toxic reagents and solvents. Easy separation, high reusability, cost-effective and mild catalyst are important advantages of the new catalyst in comparison to other catalysts for the synthesis of acridinedione derivatives via one-pot four-component reaction. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1658 KiB

Open AccessProceeding Paper

Development and Validation of a Multi-Level Computational Protocol for Drug Repurposing in the Treatment of Bacterial Infections

by Tatiana Vieira, Rita Magalhães and Sérgio F. Sousa

Chem. Proc. 2022, 8(1), 24; https://doi.org/10.3390/ecsoc-25-11728 - 14 Nov 2021

Viewed by 923

Abstract

Here, we report the optimization of a methodology using docking and virtual screening to identify novel clinical uses for already approved drugs. The molecular targets selected were MvfR and PqsD due to their crucial role in quorum sensing and biofilm formation and development. [...] Read more.

Here, we report the optimization of a methodology using docking and virtual screening to identify novel clinical uses for already approved drugs. The molecular targets selected were MvfR and PqsD due to their crucial role in quorum sensing and biofilm formation and development. The FDA-approved subset of the ZINC database was screened after careful validation of the virtual screening protocol, and molecules obtained in the top 1% for each target were further analyzed. Presented here are the top five molecules selected for each target. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

10 pages, 1581 KiB

Open AccessProceeding Paper

Synthesis of a Symmetrical tris-Tetrazole as Isostere of a Tricarboxylic Acid: Behind New Tridentate Ligands for MOFs

by Julio C. Flores-Reyes, Perla Islas-Jácome, Atilano Gutiérrez-Carrillo, Mónica A. Rincón-Guevara, Galdina V. Suárez-Moreno, Óscar Vázquez-Vera, Leticia Lomas-Romero, Eduardo González-Zamora and Alejandro Islas-Jácome

Chem. Proc. 2022, 8(1), 25; https://doi.org/10.3390/ecsoc-25-11751 - 14 Nov 2021

Viewed by 1144

Abstract

The synthesis and characterization of three tridentate ligands for new MOFs are described. A triple aminolysis of the 1,3,5-tribenzoyl chloride with p-aminobenzoic acid gave the tricarboxylic acid 3 in 90% yield. Moreover, the same reaction, also from the 1,3,5-tribenzoyl chloride, but using [...] Read more.

The synthesis and characterization of three tridentate ligands for new MOFs are described. A triple aminolysis of the 1,3,5-tribenzoyl chloride with p-aminobenzoic acid gave the tricarboxylic acid 3 in 90% yield. Moreover, the same reaction, also from the 1,3,5-tribenzoyl chloride, but using p-aminobenzonitrile gave the new tris-benzonitrile 5 in 85% yield. Finally, this later one was treated with sodium azide and a Lewis acid to synthesize the new tris-tetrazole-based ligand 7 in 72% yield through a [3 + 2] azide-nitrile cycloaddition. It is noteworthy that the isosterism between carboxylic acids and tetrazoles may be considered to design and fabricate new MOFs with similar properties. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 233 KiB

Open AccessProceeding Paper

Bioavailability of Rapeseed Oil Fortified with Ethyl Sinapate

by Dobrochna Rabiej-Kozioł, Marek P. Krzemiński, Iwona Wiśniewska and Aleksandra Szydłowska-Czerniak

Chem. Proc. 2022, 8(1), 26; https://doi.org/10.3390/ecsoc-25-11725 - 14 Nov 2021

Viewed by 892

Abstract

In recent years, phenolic acid esters have been proposed as valuable additives in the food and cosmetic industries. Therefore, ethyl sinapate (ESA) was synthesized using an enzymatic approach. Hence, the bioaccessibility of antioxidant compounds after the in vitro digestion process of rapeseed oil [...] Read more.

In recent years, phenolic acid esters have been proposed as valuable additives in the food and cosmetic industries. Therefore, ethyl sinapate (ESA) was synthesized using an enzymatic approach. Hence, the bioaccessibility of antioxidant compounds after the in vitro digestion process of rapeseed oil fortified with ESA was evaluated. The antioxidant activity (AA) of the oil samples before and after digestion was analyzed using three spectrophotometric methods. The addition of synthesized ESA at concentrations of 0.02 and 0.5% caused a two- to ten-fold increase in the AA of the rapeseed oils. Therefore, the obtained phenolipid can be used as an efficient antioxidant in the oil industry. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

6 pages, 1118 KiB

Open AccessProceeding Paper

A New Approach for the Synthesis of N-Arylamides Starting from Benzonitriles

by Pradip Debnath

Chem. Proc. 2022, 8(1), 27; https://doi.org/10.3390/ecsoc-25-11726 - 14 Nov 2021

Viewed by 1600

Abstract

N-Arylamides are a ubiquitous component of a broad range of natural products and biologically active compounds. In this paper, a new synthetic protocol for the preparation of N-arylamides was developed via the hypervalent iodine-mediated aza-Hofmann-type rearrangement of amidines. The reaction [...] Read more.

N-Arylamides are a ubiquitous component of a broad range of natural products and biologically active compounds. In this paper, a new synthetic protocol for the preparation of N-arylamides was developed via the hypervalent iodine-mediated aza-Hofmann-type rearrangement of amidines. The reaction proceeded smoothly at 100 °C in the presence of PhINTs in toluene solvent. The requisite amidine substrates were prepared from amines and nitriles by applying the Pinner reaction approach. Considering the easy access of amidines from nitriles, the overall process is the conversion of nitriles to acetanilide and N-arylamides. As an application of the protocol, the preparation of paracetamol from 4-cyanophenol is also described. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1892 KiB

Open AccessProceeding Paper

Development and Evaluation of Eberconazole-Loaded Niosomes

by Priyadarshi Aparajay and Abhimanyu Dev

Chem. Proc. 2022, 8(1), 28; https://doi.org/10.3390/ecsoc-25-11664 - 13 Nov 2021

Cited by 1 | Viewed by 1944

Abstract

Invasive fungal infections require a long treatment schedule; however, treatment has become more cumbersome due to the development of resistance. Most antifungal moieties show systemic toxicity upon oral administration, leading to delivery of antifungal moieties via a topical route. Eberconazole (EBZ) is a [...] Read more.

Invasive fungal infections require a long treatment schedule; however, treatment has become more cumbersome due to the development of resistance. Most antifungal moieties show systemic toxicity upon oral administration, leading to delivery of antifungal moieties via a topical route. Eberconazole (EBZ) is a BCS class II drug that has poor solubility and high permeability. It is a broad-spectrum imidazole derivative, which acts as a both fungicidal and fungistatic drug by inhibiting ergosterol synthesis. Various topical creams of EBZ are available in the market, but the lack of a proper dosing schedule and rapid removal lead to poor bioavailability. Niosomes are vesicular carriers that can entrap both hydrophilic and lipophilic drugs. Niosomal formulations have been prepared using Span20 (nonionic surfactant) and cholesterol by thin-film hydration (TFH) technique. During preformulation studies, the purity of EBZ was ascertained using FT-IR and melting point studies, while the standard calibration curve was prepared using UV-visible spectroscopy. The prepared niosomal formulations were characterized for their morphology, entrapment efficiency, particle size, and zeta potential. The formulation has shown 86 ± 0.85% entrapment efficiency, while the noisome appeared in a ring-like structure during its microscopic evaluation. Further evaluations of in vitro and in vivo release studies will be performed in the future for its efficacy and antifungal activity. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 412 KiB

Open AccessProceeding Paper

An Original Method for the Synthesis of Partially Deuterated Natural Lembehyne B and the Study of Its Biological Activity

by Alexey A. Makarov, Elina Kh. Makarova, Lilya U. Dzhemileva and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 29; https://doi.org/10.3390/ecsoc-25-11629 - 12 Nov 2021

Viewed by 888

Abstract

An efficient method for the synthesis of a partially deuterated analogue of the natural neuritogenic alkynol, lembehyne B, has been developed for the first time, based on the use of a new reaction of Ti-catalyzed cross-cyclomagnesiation of O-containing 1,2-dienes and terminal aliphatic 1,2-dienes [...] Read more.

An efficient method for the synthesis of a partially deuterated analogue of the natural neuritogenic alkynol, lembehyne B, has been developed for the first time, based on the use of a new reaction of Ti-catalyzed cross-cyclomagnesiation of O-containing 1,2-dienes and terminal aliphatic 1,2-dienes using EtMgBr in high yield. The introduction of two deuterium atoms is carried out at the stage of treatment of the formed in situ magnesacyclopentane with D₂O. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 399 KiB

Open AccessProceeding Paper

An Original Method for the Synthesis and Study of the Biological Activity of Natural Lembehyne B Aromatic Analogs

by Alexey A. Makarov, Elina Kh. Makarova, Lilya U. Dzhemileva and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 30; https://doi.org/10.3390/ecsoc-25-11630 - 12 Nov 2021

Viewed by 810

Abstract

In the development of earlier-initiated studies on the synthesis of natural and synthetic neuritogenic alkynols, lembehynes A–C—which simultaneously exhibit high antitumor activity—we developed a method for the synthesis of an analogue of natural lembehyne B containing a phenyl radical in its structure. It [...] Read more.

In the development of earlier-initiated studies on the synthesis of natural and synthetic neuritogenic alkynols, lembehynes A–C—which simultaneously exhibit high antitumor activity—we developed a method for the synthesis of an analogue of natural lembehyne B containing a phenyl radical in its structure. It is shown that the synthesized aromatic analogue of lembehyne B exhibits higher antitumor activity in vitro than a number of tumor cell lines (Jurkat, K562 and U937). Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1373 KiB

Open AccessProceeding Paper

Synthesis and Molecular Docking of N,N′-[succinylbis(oxy)]dibenzamides as Inhibitors of Cathepsin S and Cathepsin K

by Yulia A. Trukhanova, Boris Y. Lalaev and Anna A. Vakhnina

Chem. Proc. 2022, 8(1), 31; https://doi.org/10.3390/ecsoc-25-11637 - 12 Nov 2021

Viewed by 938

Abstract

The reaction of interaction of benzhydroxamic and 4-nitrobenzhydroxamic acids with succinyl chloride, carried out in an acetonitrile medium during boiling, was studied. It was revealed that the result of the reaction is the formation of N,N′-[succinylbis(oxy)]dibenzamides, the structure of which [...] Read more.

The reaction of interaction of benzhydroxamic and 4-nitrobenzhydroxamic acids with succinyl chloride, carried out in an acetonitrile medium during boiling, was studied. It was revealed that the result of the reaction is the formation of N,N′-[succinylbis(oxy)]dibenzamides, the structure of which was proved by ¹H, ¹³C NMR. Using the online program PASS, the biological activity of the obtained compounds was predicted. It was found that N,N′-[succinylbis(oxy)]dibenzamides can inhibit cathepsins (enzymes that degrade protein) with a high probability. Using the online program Mcule, the molecular docking of the obtained dibenzamides and their analogs with cathepsin S and cathepsin K was carried out, and ligands with the highest affinity for the cathepsin family were identified. Using the HyperChem program, semiempirical methods were used to analyze the possibility of synthesizing suitable ligands. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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18 pages, 14496 KiB

Open AccessProceeding Paper

Interspecies Quantitative Structure-Toxicity-Toxicity Relationships for Predicting the Acute Toxicity of Organophosphorous Compounds

by Gheorghe Ilia, Ana Borota and Simona Funar-Timofei

Chem. Proc. 2022, 8(1), 32; https://doi.org/10.3390/ecsoc-25-11672 - 13 Nov 2021

Viewed by 951

Abstract

Median lethal concentration values are commonly used to express the relative risk related to the acute toxicity of chemicals. In this paper, we considered rat and mouse acute toxicity (LD₅₀) data of organophosphorous compounds (OPs) with diverse structures. Interspecies QSTTR (quantitative [...] Read more.

Median lethal concentration values are commonly used to express the relative risk related to the acute toxicity of chemicals. In this paper, we considered rat and mouse acute toxicity (LD₅₀) data of organophosphorous compounds (OPs) with diverse structures. Interspecies QSTTR (quantitative structure-toxicity–toxicity relationships) models were developed to predict the mouse oral acute toxicity using the multiple linear regression (MLR) approach. Descriptors were calculated from the OPs structures optimized by molecular mechanics calculations. Model validation was performed using several statistical parameters. The results suggest the suitability of the developed QSTTR models to reliably predict the acute toxicity of OPs. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 2930 KiB

Open AccessProceeding Paper

A Novel Synthetic Approach of Functionalised GO and CNT to Nanocomposite Containing Active Nanostructured Fillers for Classical Isocyanate Curing

by Lina Jadhav, Rahul Patil, Nikhil Borane, Satyendra Mishra, Ganapati D. Yadav, Dipak B. Patil and Vikas Patil

Chem. Proc. 2022, 8(1), 33; https://doi.org/10.3390/ecsoc-25-11679 - 13 Nov 2021

Viewed by 1214

Abstract

A novel synthetic method has been developed by utilizing the chemical reactivity of functionalized graphene and CNT with a covalent combination of chemically diverse GO/FCNT and toluene diisocyanate, thereby yielding a synergistic polymer nanocomposite. Comprehensive composite material has simultaneous covalent, as well as [...] Read more.

A novel synthetic method has been developed by utilizing the chemical reactivity of functionalized graphene and CNT with a covalent combination of chemically diverse GO/FCNT and toluene diisocyanate, thereby yielding a synergistic polymer nanocomposite. Comprehensive composite material has simultaneous covalent, as well as π-π, interactions confirming sp2-hybridized frameworks of graphene oxide and MWCNTs by Raman absorption spectra at 1345 and 1590 cm⁻¹ of D and G bands, respectively. Toluene diisocyanate and GO/FCNT inspired polymeric formulation was obtained by the classical curing reaction initiated by ultrasound sonication. This method allowed 50 wt.% doping of GO/FCNT without segregation and ensured good adhesion to the law steel surface. The large surface area and morphological character of GO and FCNT by SEM and TEM ensure stable and dispersed integrated molecules. This has advantages over high-temperature and hazardous curing reaction, and overcomes the problem of graphene exfoliation. It also does not allow CNT slipping within the bundle, which can cause falling apart at higher concentration. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1911 KiB

Open AccessProceeding Paper

Synthesis of Microcapsules with Beeswax Core and Phenol-Formaldehyde Shell by Taguchi Method

by Tejashree Amberkar and Prakash Mahanwar

Chem. Proc. 2022, 8(1), 34; https://doi.org/10.3390/ecsoc-25-11671 - 13 Nov 2021

Cited by 1 | Viewed by 977

Abstract

The Taguchi method was used to evaluate the effect of process parameters in the microencapsulation process of beeswax with resorcinol modified phenol-formaldehyde shell. An orthogonal array of 5³ was constructed to study the effect of process parameters’ core to shell ratio, surfactant [...] Read more.

The Taguchi method was used to evaluate the effect of process parameters in the microencapsulation process of beeswax with resorcinol modified phenol-formaldehyde shell. An orthogonal array of 5³ was constructed to study the effect of process parameters’ core to shell ratio, surfactant concentration and agitation speed on control parameter core content. The amount of core content is directly proportional to the heat storing capacity of microcapsules. Surfactant concentration, core to shell ratio, and agitation speed were optimized at 3%, 1:1, and 800 rpm, respectively. The microcapsules synthesized with optimized process parameters values possessed spherical morphology and heat transition enthalpy 148.93 J/g within temperature range 35–62 °C. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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11 pages, 7033 KiB

Open AccessProceeding Paper

Asymmetric Transfer Hydrogenation of Aryl Heteroaryl Ketones and o-Hydroxyphenyl Ketones Using Noyori-Ikariya Catalysts

by Ye Zheng, Jaime A. Martinez-Acosta, Mohammed Khimji, Luiz C. A. Barbosa, Guy J. Clarkson and Martin Wills

Chem. Proc. 2022, 8(1), 35; https://doi.org/10.3390/ecsoc-25-11774 - 14 Nov 2021

Viewed by 1894

Abstract

In 1995, Noyori and co-workers made a breakthrough with their design of practical ruthenium-based catalysts, which combined the homochiral TsDPEN ligand with a Ru(II) arene [...] Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1259 KiB

Open AccessProceeding Paper

Dysprosium(III)-Mediated Carboxylate Formation from a Schiff Base

by Julio Corredoira-Vázquez, Cristina González-Barreira, Ana M. García Deibe, Jesús Sanmartín-Matalobos and Matilde Fondo

Chem. Proc. 2022, 8(1), 36; https://doi.org/10.3390/ecsoc-25-11740 - 14 Nov 2021

Viewed by 1234

Abstract

This work describes an uncommon new case of imine hydrolysis, leading to the formation of a carboxylate group. The conditions of the media that favor this conversion, which seem to be mediated by the presence of Dy^III, are analyzed. The process [...] Read more.

This work describes an uncommon new case of imine hydrolysis, leading to the formation of a carboxylate group. The conditions of the media that favor this conversion, which seem to be mediated by the presence of Dy^III, are analyzed. The process brings about the formation of a dysprosium complex of formula {[(DyL₂)₂Na₂(H₂O)₈][Et₃NH]₂[DyL₂]₂}·14H₂O (1). Single X-ray characterization of the final product is reported. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 951 KiB

Open AccessProceeding Paper

An Efficient Synthesis and Antibacterial Activity of Some Novel 3,4–Dihydropyrimidin-2-(1H)-Ones

by Nilesh S. Pawar, Pramod N. Patil and Rajashri N. Pachpande

Chem. Proc. 2022, 8(1), 37; https://doi.org/10.3390/ecsoc-25-11720 - 14 Nov 2021

Viewed by 1237

Abstract

We have efficiently synthesized mono as well as bis and spiro cyclic products of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) by refluxing a reaction mixture of the three components in deep eutectic solvent (DES) to generating “libraries from libraries”. Synthesized Spiro fused heterotricyclic [...] Read more.

We have efficiently synthesized mono as well as bis and spiro cyclic products of 3,4-dihydropyrimidin-2(1H)-ones (DHPMs) by refluxing a reaction mixture of the three components in deep eutectic solvent (DES) to generating “libraries from libraries”. Synthesized Spiro fused heterotricyclic compounds containing urea moiety are potent against bacteria. Overall, in the antibacterial study, from the synthesized compounds, some of the 3,4–dihydropyrimidin-2-(1H)-one compounds were found to possess anti-bacterial efficacy. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 239 KiB

Open AccessProceeding Paper

Profiling the Nematicidal Activity of Linear and Cyclic Compounds on the Pinewood Nematode

by Jorge M. S. Faria, Pedro Barbosa, Cristina Moiteiro, Manuel Mota and Maria L. Inácio

Chem. Proc. 2022, 8(1), 38; https://doi.org/10.3390/ecsoc-25-11641 - 12 Nov 2021

Cited by 1 | Viewed by 1080

Abstract

The pinewood nematode (PWN), Bursaphelenchus xylophilus, has become one of the most damaging pests to forest health in Asia and Europe. In the screening for sustainable biopesticides, research has focused on highly active secondary metabolites. In the present work, 25 linear and [...] Read more.

The pinewood nematode (PWN), Bursaphelenchus xylophilus, has become one of the most damaging pests to forest health in Asia and Europe. In the screening for sustainable biopesticides, research has focused on highly active secondary metabolites. In the present work, 25 linear and cyclic pure compounds, commonly found in essential oils (EOs) and extracts, were preliminarily tested in direct contact bioassays against the PWN to understand how distinct chemical structures can be related to a stronger nematicidal activity. Their activity appeared to be strongly related to specific functional groups, isomerism, or the length of the linear carbon chain. Uncovering the variation in the structure–activity relationships of anti-PWN compounds contributes to the identification of the nematicidal mechanisms of action as a basis for improving sustainable pest management in forest ecosystems. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

9 pages, 1154 KiB

Open AccessProceeding Paper

Patentability of Biopolymer-Based Hydrogels

by Ahmed Fatimi

Chem. Proc. 2022, 8(1), 39; https://doi.org/10.3390/ecsoc-25-11653 - 13 Nov 2021

Cited by 6 | Viewed by 1441

Abstract

The most of the scientific literature shows that the studies on biopolymer-based hydrogels have a bright future. This work, in the form of a patentability study, englobes information present within patents (i.e., patent applications and granted patents) related to biopolymer-based hydrogels. The patentability [...] Read more.

The most of the scientific literature shows that the studies on biopolymer-based hydrogels have a bright future. This work, in the form of a patentability study, englobes information present within patents (i.e., patent applications and granted patents) related to biopolymer-based hydrogels. The patentability study describes the state of the art by introducing what has been patented in relation to biopolymer-based hydrogels regarding the preparation methods/process, formulations and applications. A detailed analysis is then given regarding the publication year, international patent classifications, inventors, applicants, owners, and jurisdiction. Furthermore, this work gives a competitive analysis of the past, present, and future trends in the biopolymer-based hydrogels and leads to various recommendations that could help one to plan and innovate a research strategy. The classification of patents reveals that most inventions intended for medicinal preparations characterized by special physical form, as well as materials characterized by their function or physical properties, such as hydrogels or hydrocolloids. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 813 KiB

Open AccessProceeding Paper

Photosynthesis-Inhibiting Activity of Fluorinated 2-Hydroxynaphthalene-1-carboxanilides

by Tomas Gonec, Michal Oravec and Josef Jampilek

Chem. Proc. 2022, 8(1), 40; https://doi.org/10.3390/ecsoc-25-11652 - 13 Nov 2021

Viewed by 824

Abstract

2-Hydroxy-N-phenylnaphthalene-1-carboxamide, three fluoro monosubstituted and five fluoro disubstituted 2-hydroxynaphthalene-1-carboxanilides were prepared by microwave-assisted synthesis and characterized. All the compounds were evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET inhibitory activity [...] Read more.

2-Hydroxy-N-phenylnaphthalene-1-carboxamide, three fluoro monosubstituted and five fluoro disubstituted 2-hydroxynaphthalene-1-carboxanilides were prepared by microwave-assisted synthesis and characterized. All the compounds were evaluated for their ability to inhibit photosynthetic electron transport (PET) in spinach (Spinacia oleracea L.) chloroplasts. The PET inhibitory activity of the discussed compounds proved to be in a wide range, from inactive N-(2,6-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC₅₀ = 904 μM to N-(2,5-difluorophenyl)-2-hydroxynaphthalene-1-carboxamide with an IC₅₀ of 44.2 μM, which was the most potent isomer of the series of evaluated compounds. Based on previous studies, it can be assumed that the mechanism of PET inhibition of these compounds is the inhibition of photosystem II in the thylakoid membrane. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 2379 KiB

Open AccessProceeding Paper

Exploring New Mitochondria-Targetable Theragnostic styrylBODIPYs

by Tania Mazuelo, Sergio Serrano, Fernando García-Garrido, Josué Jiménez, Carolina Díaz-Norambuena, Beatriz L. Maroto, Florencio Moreno, Jorge Bañuelos, Antonia R. Agarrabeitia, Ángeles Villanueva, Santiago de la Moya and María J. Ortiz

Chem. Proc. 2022, 8(1), 41; https://doi.org/10.3390/ecsoc-25-11677 - 13 Nov 2021

Cited by 1 | Viewed by 1042

Abstract

Two analogs of a previous mitochondria-targetable theragnostic styrylBODIPY have been designed, synthesized, and submitted to preliminary studies in order to explore their capability to act as new theragnostic agents with absorption in the red region. The new dyes are obtained through a straightforward [...] Read more.

Two analogs of a previous mitochondria-targetable theragnostic styrylBODIPY have been designed, synthesized, and submitted to preliminary studies in order to explore their capability to act as new theragnostic agents with absorption in the red region. The new dyes are obtained through a straightforward and low-cost synthetic protocol and have styryl moieties bearing non-delocalized cations (trimethylammonium) attached to the BODIPY through a spacer, or directly linked. Preliminary results of them in cell bioimaging showed internalization into HeLa cells and accumulation into mitochondria. Photodynamic therapy was also analyzed, demonstrating the viability of this red styrylBODIPY as mitochondria-targetable photo-theragnostic agent. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 1895 KiB

Open AccessProceeding Paper

Ultrasound Assisted Synthesis of 1,5-Disubstituted Tetrazoles Containing Propargyl or 2-Azidophenyl Moieties via Ugi-Azide Reaction

by Manuel A. Rentería-Gómez, César R. Solorio-Alvarado and Rocío Gámez-Montaño

Chem. Proc. 2022, 8(1), 42; https://doi.org/10.3390/ecsoc-25-11758 - 14 Nov 2021

Viewed by 1237

Abstract

A series of ten 1,5-disubstituted-1H-tetrazoles (1,5-DS-T) were synthesized via Ugi-azide isocyanide-based multicomponent reactions (IMCR) in low to good yields (30–85%), using propargyl amine or 2-azidobenzaldehyde as a component, and using ultrasound irradiation (USI) as an alternative energy source. 1,5-DS-T are useful [...] Read more.

A series of ten 1,5-disubstituted-1H-tetrazoles (1,5-DS-T) were synthesized via Ugi-azide isocyanide-based multicomponent reactions (IMCR) in low to good yields (30–85%), using propargyl amine or 2-azidobenzaldehyde as a component, and using ultrasound irradiation (USI) as an alternative energy source. 1,5-DS-T are useful heterocyclic moieties, present in many bioactive compounds and drugs. Moreover, 1,5-DS-T are used as bidentate ligands, in coordination chemistry, metal–organic framework science, bioimaging, photo-imaging, explosives, propellants, and high-energy materials. The generated products can be used as synthetic platforms for subsequent post-transformations. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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14 pages, 1565 KiB

Open AccessProceeding Paper

In Silico Evaluation of New Fluoroquinolones as Possible Inhibitors of Bacterial Gyrases in Resistant Gram-Negative Pathogens

by Manuel Alejandro Coba-Males, Javier Santamaría-Aguirre and Christian D. Alcívar-León

Chem. Proc. 2022, 8(1), 43; https://doi.org/10.3390/ecsoc-25-11753 - 14 Nov 2021

Viewed by 1650

Abstract

The work seeks to identify molecules with inhibitory activity against the DNA gyrase of Gram-negative microorganisms resistant to fluoroquinolones. Previously designed compounds were used to study antimicrobial potential in silico. Molecular docking was performed with nine new ciprofloxacin analog molecules, optimized through the [...] Read more.

The work seeks to identify molecules with inhibitory activity against the DNA gyrase of Gram-negative microorganisms resistant to fluoroquinolones. Previously designed compounds were used to study antimicrobial potential in silico. Molecular docking was performed with nine new ciprofloxacin analog molecules, optimized through the PM6/ZDO theory level, in GyrA wild type (WT) and mutant type (MT) of C. jejuni, E. coli (6RKU PDB ID), N. gonorrhoeae, P. aeruginosa, S. enteritidis, and S. typhi. The molecule with the highest affinity for GyrA was selected based on its binding free energy and inhibition constant. In addition, a retrospective docking was carried out, to guarantee the correct affinity of the ligand to the receptor at the defined binding site. The results show a molecule with greater affinity for GyrA in five microorganisms, showing a binding free energy of less than −7.0 kcal/mol, suggesting a good antibacterial activity in silico. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1872 KiB

Open AccessProceeding Paper

Organic–Inorganic Hybrid Sol–Gel Material Loaded with an Heterocyclic Aldehyde with Potential Application for Cu(II) Detection

by Rui P. C. L. Sousa, Susana P. G. Costa, Rita B. Figueira and Maria Manuela M. Raposo

Chem. Proc. 2022, 8(1), 44; https://doi.org/10.3390/ecsoc-25-11682 - 13 Nov 2021

Viewed by 1162

Abstract

Organic–inorganic hybrids (OIH) are a versatile type of material that joins organic and inorganic moieties in a polymeric matrix and can be easily synthesized by the sol–gel method. OIH can be doped with chemosensors to yield an ion-sensitive polymeric matrix that can be [...] Read more.

Organic–inorganic hybrids (OIH) are a versatile type of material that joins organic and inorganic moieties in a polymeric matrix and can be easily synthesized by the sol–gel method. OIH can be doped with chemosensors to yield an ion-sensitive polymeric matrix that can be used in the design of a more complex sensory device. Heterocyclic aldehydes show promising optical properties for supramolecular interactions with different ions through molecular recognition and changes in the optical signal. Cu(II) is a cation with biological and environmental relevance, being an appealing target for the design of chemosensors. Considering the group’s work on OIH materials and heterocyclic chromophores/fluorophores, this study reports the synthesis and characterization of an OIH based on Jeffamine THF-170 and 3-isocyanatopropyltriethoxysilane (3-ICPTES), doped with a previously synthesized heterocyclic aldehyde that features a naked-eye detection of Cu(II). Additionally, the OIH material shows color changes in the presence of Cu(II). Therefore, the obtained material shows promising properties to be used in the development of an optical fiber sensor for Cu(II) detection. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 558 KiB

Open AccessProceeding Paper

Synthesis of New Functionally Substituted Bicyclo[4.2.1]nona-2,4,7-trienes by Co(I)-Catalyzed [6π + 2π] Cycloaddition of 1-Benzoylcycloheptatriene

by Gulnara N. Kadikova, Lilya U. Dzhemileva and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 45; https://doi.org/10.3390/ecsoc-25-11631 - 12 Nov 2021

Viewed by 1021

Abstract

Functionally substituted bicyclo[4.2.1]nona-2,4,7-trienes were synthesized for the first time on the basis of the reaction of [6π + 2π] cycloaddition of hexyn-1 and 4-pentynenitrile to 1-benzoylcycloheptatriene under the action of the three-component catalytic system Co(acac)₂(dppe)/Zn/ZnI₂. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 413 KiB

Open AccessProceeding Paper

Synthesis and Antimicrobial Evaluation of Some New Pyrazole Derivatives Containing Thiazole Scaffolds

by Sachin V. Patil, Manjusha B. Suryavanshi, Deepak R. Nagargoje and Siddhant V. Kokate

Chem. Proc. 2022, 8(1), 46; https://doi.org/10.3390/ecsoc-25-11661 - 15 Nov 2021

Viewed by 1217

Abstract

In present work, one-pot synthesis of some new 2,4-disubstitued thiazolyl pyrazole derivatives was carried out. The reaction of different pyrazole 4-carbalaldehydes, thiosemicarbazides and α-haloketones in one pot afforded the target molecules. The synthesis was carried out via two methods: one conventional method, [...] Read more.

In present work, one-pot synthesis of some new 2,4-disubstitued thiazolyl pyrazole derivatives was carried out. The reaction of different pyrazole 4-carbalaldehydes, thiosemicarbazides and α-haloketones in one pot afforded the target molecules. The synthesis was carried out via two methods: one conventional method, whereby pyrazole 4-carbaldehydes, thiosemicarbazides, and α-haloketones were refluxed in ethanol; and a second way, where the reaction mixture was ground at RT. The rate of the reaction, yield of the products, and purity of the products were compared for both methods. All of the synthesized compounds were tested for their antimicrobial activities. It was found that most of the compounds showed good-to-moderate antibacterial as well as antifungal activities. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 429 KiB

Open AccessProceeding Paper

Co(I)-Catalyzed [4π + 2π] Cycloaddition of 1,2-Dienes to 1,3,5-Cyclooctatriene in the Synthesis of Previously Undescribed Tricyclo[4.2.2.0^2,5]Decenes

by Gulnara N. Kadikova, Lilya U. Dzhemileva and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 47; https://doi.org/10.3390/ecsoc-25-11633 - 12 Nov 2021

Viewed by 1141

Abstract

The catalytic [4π + 2π]-cycloaddition of monosubstituted and disubstituted 1,2-dienes to 1,3,5-cyclooctatriene under the action of Co(acac)₂(dppe)/Zn/ZnI₂ was performed for the first time to produce substituted tricyclo[4.2.2.0^2,5]dec-7-enes. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 815 KiB

Open AccessProceeding Paper

Quantitative Structure–Property Relationship for the Retention Index of Volatile and Semi-Volatile Compounds of Coffee

by Cristian Rojas, Christian D. Alcívar León, Elizabeth Contreras Aguilar, Paola V. Mazón Ayala and Doménica Muñoz

Chem. Proc. 2022, 8(1), 48; https://doi.org/10.3390/ecsoc-25-11731 - 14 Nov 2021

Cited by 1 | Viewed by 1654

Abstract

This study describes the development of a quantitative structure–property relationship to predict the retention indices of volatile and semi-volatile compounds identified in Arabica coffee samples from different geographical origins. The analytical method utilized rapid headspace solid-phase microextraction (HSSPME)–gas chromatography–time-of-flight mass spectrometry (GC-TOFMS) data [...] Read more.

This study describes the development of a quantitative structure–property relationship to predict the retention indices of volatile and semi-volatile compounds identified in Arabica coffee samples from different geographical origins. The analytical method utilized rapid headspace solid-phase microextraction (HSSPME)–gas chromatography–time-of-flight mass spectrometry (GC-TOFMS) data measured in divinylbenzene/carboxen/polydimethylsiloxane (DVB/CAR/PDMS) fiber. A total of 102 molecules were optimized with the PM6/ZDO level of theory in order to calculate several molecular descriptors. Ordinary least squares were coupled with genetic algorithm–supervised variable subset selection to find the best three descriptors. For model validation, the dataset was split into a training set (70%) and a test set (30%). The quality of the model was evaluated by means of the coefficient of determination and the root-mean-square error. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 741 KiB

Open AccessProceeding Paper

Unsaturated Fatty Acid 10H2DA Content in Serbian Royal Jelly and Its Effects on Motility of Colorectal Carcinoma Cell Lines

by Milena M. Jovanović, Dragana S. Šeklić, Milena D. Vukić, Nenad L. Vuković, Nevena S. Planojević and Snežana D. Marković

Chem. Proc. 2022, 8(1), 49; https://doi.org/10.3390/ecsoc-25-11636 - 12 Nov 2021

Viewed by 1095

Abstract

Royal jelly (RJ) is natural bee product with multiple medicinal properties that have been mainly attributed to its active compound fatty acid 10H2DA. Herein, we determined its content in RJ sampled in Serbia, and analyzed its anti-migratory activity on colorectal carcinoma cells. This [...] Read more.

Royal jelly (RJ) is natural bee product with multiple medicinal properties that have been mainly attributed to its active compound fatty acid 10H2DA. Herein, we determined its content in RJ sampled in Serbia, and analyzed its anti-migratory activity on colorectal carcinoma cells. This is the first report of the 10H2DA concentration in Serbian RJ, which is 0.92%. This acid was potent in inhibiting the motility of very aggressive HCT-116 cell line in dose-dependent manner. Further studies are needed to be conducted, especially more detailed research regarding application of this natural product compound as complementary drug in anti-cancer treatment. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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11 pages, 5718 KiB

Open AccessProceeding Paper

Resorufin-Based Colorimetric and Fluorescent Probe for Selective Detection of Mercury (II)

by Milind Shamrao Thakare, Dipak B. Patil, Siddhant V. Kokate and Nilesh S. Pawar

Chem. Proc. 2022, 8(1), 50; https://doi.org/10.3390/ecsoc-25-11779 - 14 Nov 2021

Viewed by 1279

Abstract

Environmental pollution crisis, particularly mercury ions (Hg²⁺) contamination, seriously threatens the health of all living organisms. Many studies have shown that even extremely low concentrations of Hg²⁺ can rigorously damage living organisms. Therefore, it is very much needed for real-time [...] Read more.

Environmental pollution crisis, particularly mercury ions (Hg²⁺) contamination, seriously threatens the health of all living organisms. Many studies have shown that even extremely low concentrations of Hg²⁺ can rigorously damage living organisms. Therefore, it is very much needed for real-time detection of Hg²⁺. To tackle mercury contamination and for its detection, we herewith proposed an intelligent design of a new fluorescent ‘turn-on’ probe, which was prepared based on the mercury-promoted hydrolysis of vinyl ether moiety. The probe rapidly reacted with mercury ions and showed good selectivity over other metal ions. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1417 KiB

Open AccessProceeding Paper

Synthesis of Triterpenoid-Derived α-Acyloxycarboxamides via Passerini Reaction

by Fidel Rodríguez-López, Hugo A. García-Gutiérrez and Rocío Gámez-Montaño

Chem. Proc. 2022, 8(1), 51; https://doi.org/10.3390/ecsoc-25-11785 - 14 Nov 2021

Viewed by 1174

Abstract

Herein we describe the synthesis of a small series of α-acyloxycarboxamides via a facile and efficient one-pot procedure, employing a plant-derived triterpenoid as carboxylic acid component. The products were obtained in overall yields of 25 to 79%, while we scoped the effect of [...] Read more.

Herein we describe the synthesis of a small series of α-acyloxycarboxamides via a facile and efficient one-pot procedure, employing a plant-derived triterpenoid as carboxylic acid component. The products were obtained in overall yields of 25 to 79%, while we scoped the effect of the nature of the aldehyde component on the reaction yields. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 330 KiB

Open AccessProceeding Paper

Transformation of Dialkyl-Substituted Alkynes under the Action of the TaCl₅-Mg and NbCl₅-Mg Reagent System

by Azat M. Gabdullin, Oleg S. Mozgovoj, Rita N. Kadikova, Ilfir R. Ramazanov and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 52; https://doi.org/10.3390/ecsoc-25-11680 - 13 Nov 2021

Viewed by 929

Abstract

A regioselective method for the preparation of p-tolyl-substituted alkanes is presented based on the reaction of dialkyl-substituted alkynes with four equivalents of TaCl₅ or NbCl₅ in the presence of stoichiometric amounts of metallic magnesium in toluene solution. It was found [...] Read more.

A regioselective method for the preparation of p-tolyl-substituted alkanes is presented based on the reaction of dialkyl-substituted alkynes with four equivalents of TaCl₅ or NbCl₅ in the presence of stoichiometric amounts of metallic magnesium in toluene solution. It was found that the reaction of 5-decyne with the TaCl₅-M reagent system (where M = Mg, Zn, Fe, Sm, Al, and Mn) in a toluene solution is accompanied by the selective formation of 1-(decan-5-yl)-4-methylbenzene in high yields (79–90%). The effect of solvents on the selectivity of the conversion of 5-decyne under the action of the TaCl₅-Mg reagent system has been studied. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

5 pages, 1573 KiB

Open AccessProceeding Paper

A Novel Heterocyclic Thiosemicarbazone: Synthesis, Characterization and Preliminary Sensing Studies for Ions

by Maria Lene F. Jardim, Maria Manuela M. Raposo and Susana P. G. Costa

Chem. Proc. 2022, 8(1), 53; https://doi.org/10.3390/ecsoc-25-11760 - 14 Nov 2021

Viewed by 1033

Abstract

Over the past few decades, interest in the fast and sensitive recognition and detection of molecules and ions with biological and/or environmental relevance has increased. Therefore, the search for new molecules capable of coordinating these analytes is an important topic of investigation, especially [...] Read more.

Over the past few decades, interest in the fast and sensitive recognition and detection of molecules and ions with biological and/or environmental relevance has increased. Therefore, the search for new molecules capable of coordinating these analytes is an important topic of investigation, especially concerning those with an optical response (via color or fluorescence changes). Thiosemicarbazones are versatile organic compounds due to their wide range of biological activities and interesting optical, electronic and redox properties. Additionally, they possess various binding sites, whose complexing ability can be tuned by the introduction of substituents of different electronic character. Having this in mind, we report the synthesis of a new thiosemicarbazone derivative functionalized with a quinoline moiety. The new compound was characterized by ¹H and ¹³C NMR, UV-vis absorption and fluorescence spectroscopies. Moreover, a preliminary chemosensory study was undertaken in acetonitrile solutions in the presence of relevant ions with biological, medicinal and environmental relevance, showing that this receptor has potential application as a fluorimetric chemosensor. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 1946 KiB

Open AccessProceeding Paper

Reaction of N-(tosylmethyl)ureas with NaCN: Synthetic and Mechanistic Aspects

by Anastasia A. Fesenko and Anatoly D. Shutalev

Chem. Proc. 2022, 8(1), 54; https://doi.org/10.3390/ecsoc-25-11759 - 14 Nov 2021

Viewed by 1649

Abstract

The reaction of NaCN with N-(tosylmethyl)ureas, prepared by condensation of urea with aldehydes and p-toluenesulfinic acid, was studied. Generally, this reaction afforded the corresponding α-ureido nitriles. Some mechanistic aspects of cyanide-anion amidoalkylation with N-(tosylmethyl)ureas were discussed based on DFT calculations. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 786 KiB

Open AccessProceeding Paper

Synthesis and Biological Evaluation of Some Substituted Benzimidazole Derivatives

by Sunila Patil, Parloop Bhatt, Hemant Suryawanshi, Javesh Patil and Rajesh Chaudhari

Chem. Proc. 2022, 8(1), 55; https://doi.org/10.3390/ecsoc-25-11764 - 14 Nov 2021

Viewed by 1292

Abstract

In the current research work, the title compounds 5-ethoxy-benzimidazole, were synthesized by nitration of phenacetin with concentrated nitric acid it gives N-(2-nitro-5-ethoxyphenyl) acetamide (I), which on reduction with alcohol gives 5-ethoxy-2-nitroaniline (II). Reaction of hydrazine hydrate with 5-ethoxy-2-nitroaniline produced 5-ethoxy ortho phenylene diamine [...] Read more.

In the current research work, the title compounds 5-ethoxy-benzimidazole, were synthesized by nitration of phenacetin with concentrated nitric acid it gives N-(2-nitro-5-ethoxyphenyl) acetamide (I), which on reduction with alcohol gives 5-ethoxy-2-nitroaniline (II). Reaction of hydrazine hydrate with 5-ethoxy-2-nitroaniline produced 5-ethoxy ortho phenylene diamine (III). The substituted acids reacted with 5-ethoxy ortho phenylene diamine then yielded the corresponding 5-ethoxy-benzimidazole (IV). The identification and characterization of the synthesized compounds were carried out by Elemental analysis, melting point, Thin Layer Chromatography, FT-IR, NMR and Mass data. The synthesized compounds were evaluated for anti-tubercular activity. The test compounds were subjected to in vitro screening by the tube dilution technique employing the human virulent H₃₇R_V strain of M. tuberculosis. The test compounds IVa, IVc and IVd showed significant anti-tubercular activity against H₃₇R_V strain of Mycobacterium tuberculosis. The minimum inhibitory concentration (MIC) values were found in the range of 0.8 to 12.5 μg/mL compared with the standard drugs Isoniazid. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 532 KiB

Open AccessProceeding Paper

Formulation and Evaluation of Verdant Tablets Containing Saponin-Coalesced Silver Nanoparticles Got from Fenugreek Seed Extract

by Javesh Patil, Hamid Sayyed, Hemant Suryawanshi and Bhavika Patil

Chem. Proc. 2022, 8(1), 56; https://doi.org/10.3390/ecsoc-25-11765 - 14 Nov 2021

Cited by 5 | Viewed by 1922

Abstract

Presently, nanoparticles are in demand due to several applications. Commercially used metallic nanoparticles are usually comprised of synthetic chemicals. These chemicals are noxious and combustible. Current research had the objective to explore the advantages of nanoparticles using herbal material; hence, we developed silver [...] Read more.

Presently, nanoparticles are in demand due to several applications. Commercially used metallic nanoparticles are usually comprised of synthetic chemicals. These chemicals are noxious and combustible. Current research had the objective to explore the advantages of nanoparticles using herbal material; hence, we developed silver nanoparticles of aqueous extract of Trigonellafoenum-graecum (Fenugreek) seeds and formulated them into tablets. Fenugreek seeds contain steroidal sapogenins and are responsible for the reduction of blood cholesterol levels, control diabetes, enhance breast milk production, digestion aid, and helps in weight loss hence prepared formulation can be recommended in all the above cases. The pre-compression parameters evaluated for formulations are bulk density, tapped density, Carr’s index, Hausner’s ratio, and angle of repose, and the results are 0.16 gm/cc, 0.86 gm/cc, 14.16, ratio 1.13 and 32°, respectively; whereas post-compression parameters are weight variation, friability, hardness, thickness, and disintegration, and the results are 0.504 gm, 0.2%, 3.21 gm/cm², 2.55 mm, and 7 min, respectively. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 495 KiB

Open AccessProceeding Paper

Synthesis and Antibacterial Activity of Thymyl Ethers

by Jagdish U. Patil, Pramod Nagraj Patil and Nilesh S. Pawar

Chem. Proc. 2022, 8(1), 57; https://doi.org/10.3390/ecsoc-25-11747 - 14 Nov 2021

Cited by 1 | Viewed by 1048

Abstract

In this paper, we report herein a simple and efficient synthesis method of thymyl ethers for structural modifications of natural products such as monoterpenoids and studies of ether derivatives of thymol in biological importance. Our investigations showed that thymol reacts very smoothly with [...] Read more.

In this paper, we report herein a simple and efficient synthesis method of thymyl ethers for structural modifications of natural products such as monoterpenoids and studies of ether derivatives of thymol in biological importance. Our investigations showed that thymol reacts very smoothly with different types of substituted acetanilides. The synthesized compounds were tested for their bacterial potency against four bacterial species. Such a structural modification will be beneficial to designing active molecules for pest management. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 391 KiB

Open AccessProceeding Paper

Stereoselective Synthesis and Cytotoxic Activity of Aromatic Polyether Macrodiolides Containing 1Z,5Z-Diene Moiety

by Ilgiz Islamov, Adelya Yusupova, Lilya U. Dzhemileva and Usein Dzhemilev

Chem. Proc. 2022, 8(1), 58; https://doi.org/10.3390/ecsoc-25-11763 - 15 Nov 2021

Viewed by 943

Abstract

The synthesis of previously undescribed aromatic polyether macrodiolides containing a 1Z,5Z-diene moiety was carried out in 56–72% yields and with >98% stereoselectivity. It has been shown that the synthesized macrodiolides exhibit higher cytotoxic activity in vitro against a number [...] Read more.

The synthesis of previously undescribed aromatic polyether macrodiolides containing a 1Z,5Z-diene moiety was carried out in 56–72% yields and with >98% stereoselectivity. It has been shown that the synthesized macrodiolides exhibit higher cytotoxic activity in vitro against a number of tumor cell lines (Jurkat, K562 and U937). Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1096 KiB

Open AccessProceeding Paper

Green Synthesis of Fluorescent Carbon Dots through Solvothermal Treatment of Buchnania lanzan Leaf Extract

by Pradip Jana and Abhimanyu Dev

Chem. Proc. 2022, 8(1), 59; https://doi.org/10.3390/ecsoc-25-11648 - 13 Nov 2021

Viewed by 1405

Abstract

In the present work, we synthesized fluorescent carbon dots (CDs) through solvothermal treatment of Buchnania lanzan leaf extract at 160 °C for 4 h in an oven. Here, Buchnania lanzan leaves served as a renewable source of carbon. The obtained blackish brown CD [...] Read more.

In the present work, we synthesized fluorescent carbon dots (CDs) through solvothermal treatment of Buchnania lanzan leaf extract at 160 °C for 4 h in an oven. Here, Buchnania lanzan leaves served as a renewable source of carbon. The obtained blackish brown CD solution was centrifuged, and the supernatant was filtered through a syringe filter (0.22 µm). Further, the CD solution was dried in a vacuum oven to obtain a powder. The synthesized CDs were characterized by different techniques including UV–visible spectroscopy, fluorescence spectroscopy, Fourier transform infrared (FTIR), zeta potential and X-ray diffraction (XRD). The as-prepared CD solution was found to be brownish colored in daylight while exhibiting green fluorescence under UV light. The UV–visible absorption spectrum displayed characteristic shoulder peaks of CDs at 257 nm and at 356 nm. In the fluorescence spectra, excitation-dependent emission behavior of the CDs was seen, which is one of the distinct characteristics of CDs. The negative zeta potential and characteristic peaks in FTIR suggested the presence of carbonyl, amine and hydroxyl functional groups on the CD surface. The XRD spectrum exhibited a broad peak at 2θ=19°, suggesting the amorphous nature of the CDs, similar to what has been reported in earlier works. As we synthesized surface-functionalized fluorescent carbon dots from a renewable and abundant precursor, this method can be highly useful in the large-scale synthesis of carbon dots with reduced costs and will find potential applications in the fields of drug delivery, bioimaging, etc. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 874 KiB

Open AccessProceeding Paper

Synthesis of Dibenzylbutane and 9,8′-Neo-Lignans via Cyclometalation of Allylbenzene by EtAlCl₂ and Mg in the Presence of Zr ansa-Complexes

by Pavel V. Kovyazin, Pavel V. Ivchenko, Ilya E. Nifant’ev and Lyudmila V. Parfenova

Chem. Proc. 2022, 8(1), 60; https://doi.org/10.3390/ecsoc-25-11776 - 14 Nov 2021

Viewed by 984

Abstract

The aim of the research is the development of a one-pot method for the synthesis of lignans, natural compounds that show a wide spectrum of biological activities. For this purpose, the ansa-zirconocenes of various structures were tested as catalysts of allylbenzene cyclometalation [...] Read more.

The aim of the research is the development of a one-pot method for the synthesis of lignans, natural compounds that show a wide spectrum of biological activities. For this purpose, the ansa-zirconocenes of various structures were tested as catalysts of allylbenzene cyclometalation with ethylaluminum dichloride (EtAlCl₂) and Mg. The effects of the organophosphorus compounds, hexamethylphosphoramide (HMPA) and triphenylphosphine (PPh₃), on the chemo- and regioselectivity of the reaction were studied. The use of η⁵-indenyl or fluorenyl ansa-complexes with ethanediyl or dimethylsilylene bridges, as well as a biscyclopentadienyl complex with Si-bound ligands as catalysts in the presence of HMPA, yields the formation of cyclometalation products in a total yield of 70%. Cyclometalation product composition is represented by two regioisomers, 3,4-dibenzyl- and 2,4-dibenzyl-substituted alumolanes, with a ratio of (1-2):1, in which hydrolysis provides corresponding dibenzylbutane lignan and 9,8′-neo-lignan. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 667 KiB

Open AccessProceeding Paper

Ti(O-iPr)₄-EtMgBr-Catalyzed Reaction of Dialkyl-Substituted Alkynes with Et₂Zn

by Azat M. Gabdullin, Oleg S. Mozgovoj, Rita N. Kadikova, Ilfir R. Ramazanov and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 61; https://doi.org/10.3390/ecsoc-25-11639 - 12 Nov 2021

Viewed by 1445

Abstract

For the first time, the Ti(O-iPr)₄-EtMgBr carbozincation of dialkyl-substituted alkynes with Et₂Zn was carried out. It was found that the reaction of 1,2-disubstituted alkynes (5-decyne, 4-octyne, 3-hexyne) with Et₂Zn is accompanied by the regioselective formation [...] Read more.

For the first time, the Ti(O-iPr)₄-EtMgBr carbozincation of dialkyl-substituted alkynes with Et₂Zn was carried out. It was found that the reaction of 1,2-disubstituted alkynes (5-decyne, 4-octyne, 3-hexyne) with Et₂Zn is accompanied by the regioselective formation of stereoisomeric tetra-alkyl-substituted hexa-1,3-diene derivatives in high yield. It was also found that the 2-zincoethylzincation of dialkyl-substituted alkynes in the presence of catalytic amounts of Ti(O-iPr)₄ and EtMgBr does not stop at the stage of ethylzincation of the triple bond, but is accompanied by the involvement of a second alkyne molecule with the formation of two stereoisomeric hexa-1,3-diene derivatives. The effect of the solvent on the carbozincation of the dilkyl-substituted alkynes under the conditions of titanium-magnesium catalysis was studied. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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11 pages, 7734 KiB

Open AccessProceeding Paper

Design, Development, and In Silico Study of Pyrazoline-Based Mycobactin Analogs as Anti-Tubercular Agents

by Gourav Rakshit, Sheikh Murtuja and Venkatesan Jayaprakash

Chem. Proc. 2022, 8(1), 62; https://doi.org/10.3390/ecsoc-25-11767 - 14 Nov 2021

Cited by 1 | Viewed by 1096

Abstract

The pathogenicity and virulence of Mycobacterium tuberculosis has further potentiated its infectiousness, making it a killer disease, as is evident from the WHO database. Eradicating the TB epidemic by 2030 is amongst the major health targets of the United Nations Sustainable Development Goals [...] Read more.

The pathogenicity and virulence of Mycobacterium tuberculosis has further potentiated its infectiousness, making it a killer disease, as is evident from the WHO database. Eradicating the TB epidemic by 2030 is amongst the major health targets of the United Nations Sustainable Development Goals (SDGs). The increase in multidrug-resistant TB (MDR-TB) cases has challenged and prompted the scientific community to develop novel chemotherapeutic agents with novel mechanisms of action. The goal can be achieved by “conditionally essential target” (CET)-based drug design. The research pertaining to the mycobactin biosynthesis pathway (MBP) relating to iron acquisition is in a nascent stage; the pathway serves as a promising endogenous target for novel lead compound discoveries (non-specific MBP inhibitors). As a continuation of our previous research, reported by Stirret et al., 2008 and Ferreras et al., 2011, in this study we further aim to explore the structural diversity of the previously identified active molecules as this could lead to the discovery of a more potent analog. Eventually, we designed a small library of mycobactin analogs retaining diaryl-substituted pyrazoline (DAP) as the basic scaffold and tested their in silico stabilities by molecular docking (AutoDock 4.2.6). Docking of the designed molecules was performed in the active site of the MbtA receptor (by analogy with the related structure, PDB: 1MDB) to evaluate the binding modes and inhibitory profiles. The lowest energy conformation of each docked ligand was analyzed with the BIOVIA Discovery Studio Visualizer. The docking results identified GM08 and GM09 as potent inhibitors which could therefore serve as good leads. The ADMET profile also revealed satisfactory results. Furthermore, what remains to be seen is the stability of each molecule by employing MD simulation along with intracellular activity. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1930 KiB

Open AccessProceeding Paper

A Thiophene-Based Dicyanovinyl as an Anion Chemosensor

by João P. Castro, Maria Manuela M. Raposo and Susana P. G. Costa

Chem. Proc. 2022, 8(1), 63; https://doi.org/10.3390/ecsoc-25-11769 - 14 Nov 2021

Viewed by 1090

Abstract

In recent years, push–pull dicyanovinyl derivatives have been reported for several optical applications, including as fluorescent probes for cyanide ion detection. In the presence of cyanide ions, this type of compound exhibits an ICT mechanism associated with the addition of the cyanide ion [...] Read more.

In recent years, push–pull dicyanovinyl derivatives have been reported for several optical applications, including as fluorescent probes for cyanide ion detection. In the presence of cyanide ions, this type of compound exhibits an ICT mechanism associated with the addition of the cyanide ion to the β position of the dicyanovinyl group, due to the strong electron-withdrawing effect of the cyano groups. These structural changes caused by the addition reaction are accompanied by changes in the probe’s absorption and emission. In this work, we report a thiophene-based dicyanovinyl derivative and its prospective application as an anion chemosensor. The photophysical characterization was carried out in acetonitrile and aqueous acetonitrile solutions. Preliminary sensing assays in the presence of various anions of biological, medicinal, and environmental relevance were conducted, and the interaction with CN⁻ was further explored through spectrophotometric titrations. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 580 KiB

Open AccessProceeding Paper

Azide-Alkyne Cycloaddition Catalyzed by a Glucose/Benedict Reagent System

by Jesús G. García Torres, Andrés F. Becerra-Buitrago, Luis Carlos García-Sánchez, Marco A. García-Eleno, M. V. Basavanag Unnamatla and Erick Cuevas-Yañez

Chem. Proc. 2022, 8(1), 64; https://doi.org/10.3390/ecsoc-25-11634 - 12 Nov 2021

Cited by 1 | Viewed by 1754

Abstract

Benedict’s Reagent is commonly used in identifying reducing sugars through a redox process where a Cu(I) species is generated. Despite the simplicity of this reaction, this has barely been investigated as a copper (I) source for catalytic processes. In this report, diverse organic [...] Read more.

Benedict’s Reagent is commonly used in identifying reducing sugars through a redox process where a Cu(I) species is generated. Despite the simplicity of this reaction, this has barely been investigated as a copper (I) source for catalytic processes. In this report, diverse organic azides and alkynes were reacted in the presence of catalytic amounts of a Glucose–Benedict Reagent system, obtaining the corresponding 1,2,3-triazoles through a simple and environmentally friendly synthetic procedure. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 451 KiB

Open AccessProceeding Paper

Synthesis and In Silico Evaluation of Potential Insecticide Activity of Benzamides

by Miguel A. F. Ribeiro, Tatiana F. Vieira, Maria José G. Fernandes, Renato B. Pereira, David M. Pereira, Elisabete M. S. Castanheira, A. Gil Fortes, Sérgio F. Sousa and M. Sameiro T. Gonçalves

Chem. Proc. 2022, 8(1), 65; https://doi.org/10.3390/ecsoc-25-11770 - 14 Nov 2021

Viewed by 1148

Abstract

In order to find alternative pesticides, a series of benzamide derivatives was synthesized. An in silico inverted virtual screening protocol considering the 13 common insecticide protein targets was used to evaluate the potential insecticide activity of these molecules and identify the most likely [...] Read more.

In order to find alternative pesticides, a series of benzamide derivatives was synthesized. An in silico inverted virtual screening protocol considering the 13 common insecticide protein targets was used to evaluate the potential insecticide activity of these molecules and identify the most likely targets. The results suggest important clues for the development of this class of derivatives as alternative insecticides. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1739 KiB

Open AccessProceeding Paper

Preparation and Characterization of a Three-Component Composite Based on Polymethylmetacrylate Applied as Bone Cement

by Saeedreza Kordbache, Edris Jamshidi and Faranak Manteghi

Chem. Proc. 2022, 8(1), 66; https://doi.org/10.3390/ecsoc-25-11678 - 13 Nov 2021

Viewed by 883

Abstract

A composite based on three components including PMMA (polymethyl metacrylate), HA (hydroxyl apatite) and LDH (layered double hydroxide) was prepared, characterized and applied as bone cement. Bone cement is a biomaterial used in clinical applications to fix joint replacements in hip and knee [...] Read more.

A composite based on three components including PMMA (polymethyl metacrylate), HA (hydroxyl apatite) and LDH (layered double hydroxide) was prepared, characterized and applied as bone cement. Bone cement is a biomaterial used in clinical applications to fix joint replacements in hip and knee joints. There are four types of bone cement, two of which are polymer-based and applied in dentistry and orthopedics, including: (a) acrylic cements based on PMMA; (b) preparation cements based on PPF (polypropyl fumarate). LDH, with the general formula of [M(II)_1-xM(III)_x(OH)₂]^x+·(Aⁿ⁻)_X/n·mH₂O, has M(II) and M(III) cations and an Aⁿ⁻ inter-layer anion. The importance of LDH is its planar layered structure. HA is a thermodynamically stable calcium phosphate similar to human hard tissues in morphology and composition. In this work, we prepare a Zr-CoLDH with a green method and mix it with PMMA and HA in a given ratio. In order to characterize the composite, XRD, FTIR and SEM analyses are performed. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 5126 KiB

Open AccessProceeding Paper

Synthesis and Structural Study of a New β-Turn Inducer Peptidomimetic Incorporating 1-Amino-1-Aminomethylcyclohexane

by María Campos, Victor M. Sánchez-Pedregal, Pablo López-Carracedo, Ramón J. Estévez and Juan C. Estévez

Chem. Proc. 2022, 8(1), 67; https://doi.org/10.3390/ecsoc-25-11684 - 14 Nov 2021

Viewed by 942

Abstract

A new β-turn inducer peptidomimetic incorporating 1-amino-1-aminomethylcyclohexane (compound 3) was synthetized and structurally studied. It was established that there is a rapid conformational equilibrium between the expected β-turn inducer structure and other extended conformations. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 715 KiB

Open AccessProceeding Paper

Synthesis of N-(hydroxymethylene)thioamides by N-hydroxymethylation of 2-cyanothioacrylamides

by Arina G. Levchenko, Polina G. Dahno and Victor V. Dotsenko

Chem. Proc. 2022, 8(1), 68; https://doi.org/10.3390/ecsoc-25-11799 - 14 Nov 2021

Viewed by 1028

Abstract

The condensation products of cyanothioacetamide with aldehydes—(E)-arylmethylenecyanothioacetamides—have proven to be readily available and multifunctional starting reagents in the chemistry of S,N-containing compounds. We decided to study the interaction of formaldehyde with thioamides as a possible way to obtain N-(hydroxymethylene)thioamides, which are promising thioamidoalkylating [...] Read more.

The condensation products of cyanothioacetamide with aldehydes—(E)-arylmethylenecyanothioacetamides—have proven to be readily available and multifunctional starting reagents in the chemistry of S,N-containing compounds. We decided to study the interaction of formaldehyde with thioamides as a possible way to obtain N-(hydroxymethylene)thioamides, which are promising thioamidoalkylating agents and new ligands for complexation. It was found that the reaction of thioamides and formaldehyde proceeds easily when the reagents are heated in the absence of catalysts in an aqueous-alcohol medium, and leads, with good yields, to the expected N-(hydroxymethylene)thioamides. The structure of N-(hydroxymethylene)thioamides 2 was confirmed by IR and NMR spectroscopy data. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 402 KiB

Open AccessProceeding Paper

Asian Hornet, Vespa velutina Lepeletier 1836 (Hym.: Vespidae), Venom Obtention Based on an Electric Stimulation Protocol

by Xesús Feás, M. Pilar Vázquez-Tato and Julio A. Seijas

Chem. Proc. 2022, 8(1), 69; https://doi.org/10.3390/ecsoc-25-11723 - 14 Nov 2021

Viewed by 954

Abstract

The yellow-legged Asian hornet (AH) (Vespa velutina Lepeletier 1836 (Hymenoptera: Vespidae)) is naturally distributed in China, Southeast Asia, and India; however, it has been detected outside of its native area, confirmed as being established in South Korea, Europe, and Japan. Health risks [...] Read more.

The yellow-legged Asian hornet (AH) (Vespa velutina Lepeletier 1836 (Hymenoptera: Vespidae)) is naturally distributed in China, Southeast Asia, and India; however, it has been detected outside of its native area, confirmed as being established in South Korea, Europe, and Japan. Health risks and deaths caused by AH stings have become a public health concern. In the present work, a quick, straightforward, and inexpensive method for obtaining AH venom by electric stimulation is described. The availability of AH venom will lead to improved diagnostic and therapeutic methods, mainly by venom immunotherapy (VIT) in patients allergic to this invasive species. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1323 KiB

Open AccessProceeding Paper

Palladacycles as Functionalized Metal-Ligand Precursors, Contain Tridentate [Csp², N, S] Ligands

by Basma Al Janabi, Jose Manuel Vila and Juan M. Ortigueira

Chem. Proc. 2022, 8(1), 70; https://doi.org/10.3390/ecsoc-25-11663 - 13 Nov 2021

Viewed by 941

Abstract

The reactivity of R–CH=N–(C6H4–2–SMe) with R = 4–Br–C6H5, R = 3–Br–C6H5, R = 2–Cl–C6H5 with palladium (II) salts was investigated in this study. We were able to prepare and characterize the cyclometallation complexes. The thioimines act as a [Csp2, phenyl, N, S] tridentate [...] Read more.

The reactivity of R–CH=N–(C6H4–2–SMe) with R = 4–Br–C6H5, R = 3–Br–C6H5, R = 2–Cl–C6H5 with palladium (II) salts was investigated in this study. We were able to prepare and characterize the cyclometallation complexes. The thioimines act as a [Csp2, phenyl, N, S] tridentate group, according to the X-ray crystal structures in the latter complex. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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12 pages, 3201 KiB

Open AccessProceeding Paper

Weak Donor, Strong Acceptor Thienopyrazine-Based Polymers for Fine Tuning of LUMO Levels—Suitable Materials for Energy and Storage Solutions

by Benedetta Maria Squeo, Elisa Lassi, Chiara Botta, Silvia Luzzati, Barbara Vercelli, Stefania Zappia and Mariacecilia Pasini

Chem. Proc. 2022, 8(1), 71; https://doi.org/10.3390/ecsoc-25-11742 - 14 Nov 2021

Viewed by 1448

Abstract

One approach creating and to tuning the energy levels of small band gap polymers or molecules is alternating donor-like (electron donating) and acceptor-like (electron withdrawing) monomers. Polymer for solar cells need to maintain a low highest occupied molecular orbital (HOMO) energy level in [...] Read more.

One approach creating and to tuning the energy levels of small band gap polymers or molecules is alternating donor-like (electron donating) and acceptor-like (electron withdrawing) monomers. Polymer for solar cells need to maintain a low highest occupied molecular orbital (HOMO) energy level in order to maximize the open circuit voltage (V_oc) and have a small band gap in order to maximize the short-circuit current (J_sh). Alternating a “weak donor” and a “strong acceptor” will maintain a low HOMO energy level and reduce the band gap via intramolecular charge transfer (ICT). Here we present the synthesis and characterization of a series of polymers based on thienopyrazine (acceptor) and carbazole (donor). We compared the optoelectronic properties of the classic polymer poly-carbazole-dithiophene-benzothiadiazole (PCDTBT) with one where benzothiadiazole was substituted with thienopyrazine and one where we randomly alternated thienopyrazine and benzothiadiazole as the acceptor unit while maintaining the same donor unit. The approach of alternating weak donor and strong acceptor moieties allowed us to obtain fine LUMO level modulation of the materials, opening the way to the design of new donor materials. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 2462 KiB

Open AccessProceeding Paper

Peptides Incorporating 3,4-Dihydroxyprolines: Synthesis and Structural Study

by Rosalino Balo, Alejandro Jiménez, David Reza, Ramón J. Estévez and Juan C. Estévez

Chem. Proc. 2022, 8(1), 72; https://doi.org/10.3390/ecsoc-25-11683 - 13 Nov 2021

Viewed by 940

Abstract

Although the most common types of secondary structures in proteins are helices and sheets, other types of structures also form, such as turns and loops. Turns play an important role, both structurally and functionally. With regard to the structural aspect, they intervene in [...] Read more.

Although the most common types of secondary structures in proteins are helices and sheets, other types of structures also form, such as turns and loops. Turns play an important role, both structurally and functionally. With regard to the structural aspect, they intervene in the folding of the peptide chain, favoring the formation of a specific tertiary, globular or fibrous structure. With regard to the functional aspect, the turns are mainly located in the region of the proteins most exposed to the environment and, therefore, influence various processes, such as molecular and cellular recognition as well as interactions between peptide structures and nonpeptide substrates or receptors. In addition, the turns serve as templates for the design of new drugs, antigens and pesticides. The serine−proline sequence, in terms of its ability to induce β-turns, is present in proteins that regulate gene expression and DNA binding. In addition, this sequence is recognized as a substrate by numerous kinases, representing a preferential site for protein phosphorylation. As an application of our work on the synthesis of dihydroxyprolines, we will discuss the ability of the dihydroxyproline−proline domain to induce the formation of β-turns similar to those induced by the serine−proline pair in synthetic peptides. To this end, it is proposed to incorporate the proline−dihydroxyproline dimer (in blue) into peptide II. This novel peptide supports the possibility of the formation of hydrogen bonds similar to those of peptide I, which incorporates the serine−proline sequence (in blue). Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 760 KiB

Open AccessProceeding Paper

Synthesis and Characterization of Amine-Functionalized Thiosemicarbazone Cyclopalladated Compounds

by Francisco Reigosa, María Teresa Pereira and José Manuel Vila

Chem. Proc. 2022, 8(1), 73; https://doi.org/10.3390/ecsoc-25-11762 - 14 Nov 2021

Viewed by 955

Abstract

Differences in the functional groups of the ligands can change the properties of the cyclometallated compounds and modify their suitability for various applications, such as catalysis and biomedicine. Herein, we report the synthesis and characterization of a new series of cyclometallated palladium compounds [...] Read more.

Differences in the functional groups of the ligands can change the properties of the cyclometallated compounds and modify their suitability for various applications, such as catalysis and biomedicine. Herein, we report the synthesis and characterization of a new series of cyclometallated palladium compounds bearing an amine-functionalized thiosemicarbazone. The synthesis of the ligands was achieved by condensation of the thiosemicarbazide and aminoacetophenone. The reaction of the ligands with an appropriate metallating agent gave rise to the tetranuclear cyclometallated compounds. The compounds were characterized by EA, ¹H-NMR and IR spectroscopy. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 4208 KiB

Open AccessProceeding Paper

An Convenient Synthesis of Ricinine and Its Analogues

by Didier Villemin, Florian Faucher, Nathalie Bar, Zahira Kibou and Noureddine Choukchou-Braham

Chem. Proc. 2022, 8(1), 74; https://doi.org/10.3390/ecsoc-25-11676 - 13 Nov 2021

Viewed by 1611

Abstract

Ricinine is an alkaloid of Ricinus communis that displays numerous biological properties. Ricinine (4-methoxy-1-methyl-2-oxo-dihydropyridine-3-carbonitrile)) and new N-analogues of Ricinine were obtained by the reaction of ethyl α-ethoxyethylidenecyanoacetate with various amines. Earlier, ethyl α-ethoxyethylidenecyanoacetate was easily prepared from ethyl cyanoacetate. Biologically, amines such as [...] Read more.

Ricinine is an alkaloid of Ricinus communis that displays numerous biological properties. Ricinine (4-methoxy-1-methyl-2-oxo-dihydropyridine-3-carbonitrile)) and new N-analogues of Ricinine were obtained by the reaction of ethyl α-ethoxyethylidenecyanoacetate with various amines. Earlier, ethyl α-ethoxyethylidenecyanoacetate was easily prepared from ethyl cyanoacetate. Biologically, amines such as tryptamine and histamine were used in order to introduce a second pharmacophore on the target molecule. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 734 KiB

Open AccessProceeding Paper

3R-Substituted and Norbornane-Annelated 1H-Phospholanoxides: Synthesis and Structure

by Alevtina L. Makhamatkhanova, Rimma R. Nurislamova, Vladimir A. D’yakonov and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 75; https://doi.org/10.3390/ecsoc-25-11708 - 14 Nov 2021

Cited by 1 | Viewed by 847

Abstract

A method for the synthesis of 3R-substituted and norbornane-annelated 1H-phospholan oxides has been developed. The method is based on the in situ substitution of the Al atom by the P atom in five-membered cyclic alumolanes using phosphorus trichloride. Substituted alumolanes were [...] Read more.

A method for the synthesis of 3R-substituted and norbornane-annelated 1H-phospholan oxides has been developed. The method is based on the in situ substitution of the Al atom by the P atom in five-membered cyclic alumolanes using phosphorus trichloride. Substituted alumolanes were prepared by the reaction of cycloalumination of aliphatic and aromatic α-olefins and norbornene derivatives with triethylaluminum in the presence of bis(cyclopentadienyl)zirconium(IV) dichloride catalyst. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 2649 KiB

Open AccessProceeding Paper

Synthesis and Characterization of a Dansyl-Based Fluorescent Probe for Analytical Purposes

by Jesús Sanmartín-Matalobos, Pilar Bermejo-Barrera, Yeneva Alves-Iglesias, Ana M. García-Deibe and Matilde Fondo

Chem. Proc. 2022, 8(1), 76; https://doi.org/10.3390/ecsoc-25-11775 - 14 Nov 2021

Cited by 2 | Viewed by 1460

Abstract

With the aim of investigating the development of an easily synthesized dansyl-based fluorescent probe for detecting heavy-metal-based nanomaterials in aqueous solution, we synthetized and characterized a Schiff-base ligand, which we named H₃L. It was derived from the reaction of 4-formyl-3-hydroxybenzoic acid [...] Read more.

With the aim of investigating the development of an easily synthesized dansyl-based fluorescent probe for detecting heavy-metal-based nanomaterials in aqueous solution, we synthetized and characterized a Schiff-base ligand, which we named H₃L. It was derived from the reaction of 4-formyl-3-hydroxybenzoic acid with N-(2-aminobenzyl)-5-(dimethylamino)naphthalene-1-sulfonamide. H₃L incorporates a suitable O,N-binding domain that can bind heavy-metal ions at the surface of the nanoparticles. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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16 pages, 8770 KiB

Open AccessProceeding Paper

Molecular Docking Study of Flavonoids to Block the Aryl Hydrocarbon Receptor

by Oscar Collado García, Hans De Winter, Paul Cos, Maria João Matos, Eugenio Uriarte, Gabriel Llaurado Maury, Jorrit De Waele, Glay Chinea Santiago and Enrique Molina

Chem. Proc. 2022, 8(1), 77; https://doi.org/10.3390/ecsoc-25-11766 - 14 Nov 2021

Cited by 1 | Viewed by 1921

Abstract

Anti-HIF flavonoids have been described for their antitumor activity by interfering with a presumed antioxidant mechanism through direct and indirect ways of overexpression of the hypoxia inducible factor (HIF-1α). The aryl hydrocarbon receptor (AhR) is a protein homologous to HIF-1α and is overexpressed [...] Read more.

Anti-HIF flavonoids have been described for their antitumor activity by interfering with a presumed antioxidant mechanism through direct and indirect ways of overexpression of the hypoxia inducible factor (HIF-1α). The aryl hydrocarbon receptor (AhR) is a protein homologous to HIF-1α and is overexpressed in smoking patients suffering from lung and breast cancer. The interaction of thirteen flavonoids with the AhR has been evaluated by molecular docking. The AhR:ARNT model obtained by SwissModel has been used for docking with the MOE 2019.01 program, as well as several servers for the determination of protein–protein interactions and alanine mutations. Different interaction sites were identified for blocking the AhR: functional ARNT, the interface between the bHLH and PAS-A domains, being important. The blocking capacity to AhR:ARNT proved to be between 50 and 60% for flavonoids 4′,7-dihydroxy-flavone, fisetin, luteolin, 5-hydroxy-2-(4′-hydroxy)-7-methoxy-flavonone, flavone, apigenin, galangin and 7-hydroxy-5-methoxy-flavonone. None of the flavonoids evaluated interact with the PAS-B domain (AhR active site). All the studied flavonoids interact with AhR, except flavone, and with ARNT except the compounds 3,7-dihydroxy-flavone and kaempferol. The best flavonoid for blocking the formation of the AhR:ARNT heterodimer proved to be fisetin, which is found in food sources such as strawberries, apples and grapes, and has shown the ability to reduce pro-cancer inflammatory markers in colorectal cancer patients and lung cancer. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 9416 KiB

Open AccessProceeding Paper

Design, Synthesis and Studies of Novel Imidazoles

by Priyanka Chandra, Swastika Ganguly and Manik Ghosh

Chem. Proc. 2022, 8(1), 78; https://doi.org/10.3390/ecsoc-25-11628 - 12 Nov 2021

Viewed by 1218

Abstract

Twenty-five novel imidazole analogs of 26(a–r) and 27(a–g) were designed, based on Quantitative Structure Activity Relationship (QSAR)studies. The designed compounds were subjected to molecular docking studies and predictive Absorption, Dissolution, Metabolism, Excretion (ADME) studies were performed. Molecular docking studies were performed in the [...] Read more.

Twenty-five novel imidazole analogs of 26(a–r) and 27(a–g) were designed, based on Quantitative Structure Activity Relationship (QSAR)studies. The designed compounds were subjected to molecular docking studies and predictive Absorption, Dissolution, Metabolism, Excretion (ADME) studies were performed. Molecular docking studies were performed in the active site of HIV-1-reverse transcriptase PDB ID: 1RT2 and glucosamine-fructose-6-phosphate animotransferase PDB ID: 2VF5. AutoDock tools v1.5.6 was used for the molecular docking studies. The binding mode analysis of the compounds was carried out. Docking studies suggested that all the compounds showed good interactions, i.e., H-bonding interactions and pi-pi interactions when compared to the standard compounds, i.e., nevirapine (in the case of PDB ID:1RT2) and metronidazole (in the case of PDB ID:2VF5). The predictive ADME studies also showed that all the compounds have drug-like properties. The results show that these compounds can be synthesized and further explored for their possible antimicrobial and antiviral activities. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 1849 KiB

Open AccessProceeding Paper

Microwave-Assisted Synthesis of Aryl Phosphonates and Tertiary Phosphine Oxides by the Hirao Reaction

by Bianka Huszár, Zoltán Mucsi and György Keglevich

Chem. Proc. 2022, 8(1), 79; https://doi.org/10.3390/ecsoc-25-11697 - 15 Nov 2021

Viewed by 913

Abstract

Our group described a green, “P-ligand-free”, Pd(OAc)₂- or NiCl₂-catalyzed synthesis under MW conditions. The reactivity of a few aryl derivatives in the Pd(OAc)₂-catalyzed, “P-ligand-free” P–C coupling reactions under MW condition was also studied. An induction period was [...] Read more.

Our group described a green, “P-ligand-free”, Pd(OAc)₂- or NiCl₂-catalyzed synthesis under MW conditions. The reactivity of a few aryl derivatives in the Pd(OAc)₂-catalyzed, “P-ligand-free” P–C coupling reactions under MW condition was also studied. An induction period was observed. Finally, the less known copper(I)-promoted reactions were investigated experimentally. The mechanism was explored by quantum chemical calculations. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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11 pages, 163285 KiB

Open AccessProceeding Paper

Computational Study of P, S and Se Analogues of Naphthalenediimide as Cathode Components in Batteries

by M. Pilar Vázquez-Tato, Francisco Meijide, José Vázquez Tato and Julio A. Seijas

Chem. Proc. 2022, 8(1), 80; https://doi.org/10.3390/ecsoc-25-11696 - 15 Nov 2021

Viewed by 766

Abstract

Several computational studies have been published to predict the behaviour of naphthalenediimides (NDI) in the transport of electrons in batteries, as well as their physical properties. This communication compares NDI with their analogues resulting from replacing the nitrogen atom by phosphorus, sulphur, or [...] Read more.

Several computational studies have been published to predict the behaviour of naphthalenediimides (NDI) in the transport of electrons in batteries, as well as their physical properties. This communication compares NDI with their analogues resulting from replacing the nitrogen atom by phosphorus, sulphur, or selenium. The calculations were performed with Gaussian 16 using the theory level B3LYP/6-311++g(d,p) in gas and in DMSO, which allows obtaining the values for IP, EA, HOMO, LUMO, Fukui indices, redox potential, and reorganization free energies. The results achieved indicate that the analogues studied could be an interesting alternative to naphthalenediimides, and that their experimental study may be new tools for lithium batteries. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 271 KiB

Open AccessProceeding Paper

Valorization of Orange Peels as a Source of Pectins

by Vanina A. Guntero and Cristián A. Ferretti

Chem. Proc. 2022, 8(1), 81; https://doi.org/10.3390/ecsoc-25-11700 - 14 Nov 2021

Viewed by 1042

Abstract

Pectin is a natural structural polymer that is extensively used in the food industry and in medicinal and pharmaceutical fields. Considering potential applications, in this study, microwave-assisted and conventional extraction were evaluated for the extraction of pectin from orange peel by acid hydrolysis [...] Read more.

Pectin is a natural structural polymer that is extensively used in the food industry and in medicinal and pharmaceutical fields. Considering potential applications, in this study, microwave-assisted and conventional extraction were evaluated for the extraction of pectin from orange peel by acid hydrolysis using citric acid as an extractant. For conventional extraction, temperatures higher than 60 °C and long extraction times were necessary to obtained pectin yields of 9.0%. Under conventional conditions of extraction, the degree of esterification of pectin was 55.0%. The extraction procedure assisted by microwave was optimized using an experimental design of 3 factors and 2 levels, and the effect of the operational variables’ influence on the pectin yield was analyzed. The optimization of the pectin extraction conditions showed that a temperature of 55 °C, an extraction time of 6 min, and a solid/liquid ratio of 0.02 mg/mL, were necessary to obtain pectin yields of 25.0%. Under the optimal extraction conditions, the degree of esterification of pectin was about 75%. According to the ANOVA analysis, time was the factor that had the greatest influence on the yields of pectin. These results showed that the microwave-assisted procedure to be obtained enabled pectin from the orange peel over mild operation conditions. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

8 pages, 568 KiB

Open AccessProceeding Paper

Synthetic Approach to Diversified Imidazo[2,1-b][1,3]thiazines and Its Evaluation as Non-Steroidal Anti-Inflammatory Agents

by Nataliia Slyvka, Serhii Holota, Lesya Saliyeva and Mykhailo Vovk

Chem. Proc. 2022, 8(1), 82; https://doi.org/10.3390/ecsoc-25-11692 - 14 Nov 2021

Viewed by 952

Abstract

The present work is devoted to the synthesis of imidazo[2,1-b][1,3]thiazine derivatives as possible anti-inflammatory agents. The synthetic approach to (2-pyridinyloxy) substituted imidazo[2,1-b][1,3]thiazines based on the interaction of the polysubstituted 2-chloropyridines with 3-hydroxy-imidazo[2,1-b][1,3]thiazines was proposed. Selective nucleophilic substitution [...] Read more.

The present work is devoted to the synthesis of imidazo[2,1-b][1,3]thiazine derivatives as possible anti-inflammatory agents. The synthetic approach to (2-pyridinyloxy) substituted imidazo[2,1-b][1,3]thiazines based on the interaction of the polysubstituted 2-chloropyridines with 3-hydroxy-imidazo[2,1-b][1,3]thiazines was proposed. Selective nucleophilic substitution in position 2 of a pyridine ring was observed in the mentioned reaction. The synthesized (2-pyridinyloxy) substituted imidazo[2,1-b][1,3]thiazines drug-like properties were studied in silico using SwissADME and anti-inflammatory activity in the carrageenan test in vivo. Hit-compounds with satisfactory drug-like and pharmacological features were identified as promising objects for forthcoming structure optimization and in-depth studies. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 576 KiB

Open AccessProceeding Paper

Eugenol Ester Derivatives: Synthesis, Insecticidal Activity and Computational Studies

by José R. A. Coelho, Tatiana F. Vieira, Renato B. Pereira, David M. Pereira, Elisabete M. S. Castanheira, A. Gil Fortes, Sérgio F. Sousa, Maria José G. Fernandes and M. Sameiro T. Gonçalves

Chem. Proc. 2022, 8(1), 83; https://doi.org/10.3390/ecsoc-25-11787 - 14 Nov 2021

Viewed by 1569

Abstract

Specific structural modifications in eugenol molecules can simultaneously improve the biological activity and reduce side effects of the respective analogues. The esterification of eugenol by two different experimental procedures, and subsequently the conversion of one of the esters into the corresponding oxirane, was [...] Read more.

Specific structural modifications in eugenol molecules can simultaneously improve the biological activity and reduce side effects of the respective analogues. The esterification of eugenol by two different experimental procedures, and subsequently the conversion of one of the esters into the corresponding oxirane, was carried out. All derivatives obtained were then evaluated for their effect on the viability of Sf9 (Spodoptera frugiperda) cells. In addition, a structured-based inverted virtual screening protocol was employed to identify the potential proteins associated with the observed insecticidal activity. The encouraging results obtained allowed us to establish a preliminary structure–activity relationship. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 1627 KiB

Open AccessProceeding Paper

Synthesis of New bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones via the Ugi-Zhu Reaction and Docking Studies on the Main Protease (M^Pro) from SARS-CoV-2

by Ivette Morales-Salazar, Sandra L. Castañón-Alonso, Daniel Canseco-González, Erik Díaz-Cervantes, Eduardo González-Zamora and Alejandro Islas-Jácome

Chem. Proc. 2022, 8(1), 84; https://doi.org/10.3390/ecsoc-25-11771 - 14 Nov 2021

Viewed by 995

Abstract

The synthesis of five new bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones in 30 to 40% yields through a domino sequence based on the Ugi-Zhu three-component reaction is described. Then, on the main protease M^Pro (PDB: 6lu7) from the SARS-CoV-2, the synthesized products and co-crystallized [...] Read more.

The synthesis of five new bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones in 30 to 40% yields through a domino sequence based on the Ugi-Zhu three-component reaction is described. Then, on the main protease M^Pro (PDB: 6lu7) from the SARS-CoV-2, the synthesized products and co-crystallized ligands of M^Pro were in silico evaluated using the docking technique, finding moderate to good binding energies and some interesting interactions, demonstrating that the ligand 8c can be considered as a drug candidate against the SARS-CoV-2-M^Pro due to its LE value (−5.96 kcal/mol), which is better than other synthesized and reported molecules in the literature. At the same time, hydrophobic interactions play a crucial role in the ligand target molecular couplings, demonstrated through a hydrophobicity surfaces analysis. Finally, 8a and 8b can also be considered as drug candidates. Thus, some synthesized bis-furanyl-pyrrolo[3,4-b]pyridin-5-ones may be used for further in vitro assays against the virus. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 244 KiB

Open AccessProceeding Paper

An Overview of Biotransformation for the Sustainability of Sweet-Tasting Proteins as Natural Sugar Replacers

by Emel Hasan Yusuf

Chem. Proc. 2022, 8(1), 85; https://doi.org/10.3390/ecsoc-25-11640 - 12 Nov 2021

Cited by 2 | Viewed by 1405

Abstract

According to WHO, sugar intake rates should be reduced due to the connection between sugar and diseases. However, reducing sugar in foods is a challenge both for food manufacturers and consumers. Therefore, sweet-tasting proteins may solve this problem with a sweet taste, health [...] Read more.

According to WHO, sugar intake rates should be reduced due to the connection between sugar and diseases. However, reducing sugar in foods is a challenge both for food manufacturers and consumers. Therefore, sweet-tasting proteins may solve this problem with a sweet taste, health benefits, and without caloric contents. Thus far, known natural sweet-tasting proteins are brazzein, curculin, thaumatin, monellin, miraculin, and mabinlin. Nevertheless, natural sources of sweet proteins might be extinct in the future due to overconsumption. Thus, biotransformation studies of sweet proteins are promising as they produce high yield rates, quality, fewer by-products, and more sustainable solutions. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

8 pages, 1324 KiB

Open AccessProceeding Paper

Greener Synthesis, In-Silico and Theoretical Analysis of Hydrazides as Potential Antituberculosis Agents (Part 1)

by Suraj N. Mali, Anima Pandey, Bapu R. Thorat and Chin-Hung Lai

Chem. Proc. 2022, 8(1), 86; https://doi.org/10.3390/ecsoc-25-11655 - 13 Nov 2021

Cited by 4 | Viewed by 1038

Abstract

Since several decades, our healthcare burden has been increased due to tremendous cases of multidrug-resistant (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) infections, especially in tropical countries. In the present study, we have synthesized ten hydrazides with the use of the greener Chitosan-derived catalyst. [...] Read more.

Since several decades, our healthcare burden has been increased due to tremendous cases of multidrug-resistant (MDR-TB) and extensively drug-resistant tuberculosis (XDR-TB) infections, especially in tropical countries. In the present study, we have synthesized ten hydrazides with the use of the greener Chitosan-derived catalyst. This catalyst accomplished the said condensation reaction within 15–30 min at room temperature conditions. All our synthesized compounds showed stronger affinities against Mycobacterium tb and bacterial targets, especially towards 1d7u, than the standard drug ciprofloxacin. One of our compounds retained a lower toxicity (electrophilicity index (ω) 3.1304), low chemical hardness (η: 2.1740), and high softness (S: 0.4600). In the realm of the development of more potent, effective, and safe antituberculosis agents with an effective greener synthesis, our current study would provide more insights on potent analogues containing hydrazine motifs in them. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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9 pages, 2958 KiB

Open AccessProceeding Paper

N,N-Dimethyl-4-amino-2,1,3-benzothiadiazole: Synthesis and Luminescent Solvatochromism

by Valentina Ferraro, Matteo Girotto and Marco Bortoluzzi

Chem. Proc. 2022, 8(1), 87; https://doi.org/10.3390/ecsoc-25-11658 - 13 Nov 2021

Cited by 1 | Viewed by 1502

Abstract

N,N-Dimethyl-4-amino-2,1,3-benzothiadiazole (BTD^NMe2) was synthesized from the commercially available 2,1,3-benzothiadiazole (BTD) by nitration in a sulfonitric mixture, followed by a reduction of the nitro group and subsequent methylation with iodomethane. BTD^NMe2 was fully characterized by means of nuclear [...] Read more.

N,N-Dimethyl-4-amino-2,1,3-benzothiadiazole (BTD^NMe2) was synthesized from the commercially available 2,1,3-benzothiadiazole (BTD) by nitration in a sulfonitric mixture, followed by a reduction of the nitro group and subsequent methylation with iodomethane. BTD^NMe2 was fully characterized by means of nuclear magnetic resonance (NMR) and infrared spectroscopy. The solutions of BTD^NMe2 in common organic solvents revealed to be appreciably luminescent in the visible range. The electronic transitions related to the absorption and emission properties were associated with the HOMO–LUMO energy gap by means of electrochemical measurements and DFT calculations. Finally, BTD^NMe2 was successfully used to prepare luminescent-doped poly(methyl methacrylate) samples. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 5192 KiB

Open AccessProceeding Paper

Synthesis of Bis-Hydrazine Using Heterogeneous Catalysis

by Nassima Medjahed, Zahira Kibou, Amina Berrichi, Redouane Bachir and Nourredine Choukchou-Braham

Chem. Proc. 2022, 8(1), 88; https://doi.org/10.3390/ecsoc-25-11706 - 14 Nov 2021

Viewed by 1330

Abstract

Hydrazine derivatives are known as a group of organic compounds containing C=N-N=C functional groups. This π-conjugated system enables electronic excitation in the visible and near-ultraviolet regions. This is of particular interest for many applications, such as corrosion inhibition dye-sensitized solar cells (DSSC), organogels, [...] Read more.

Hydrazine derivatives are known as a group of organic compounds containing C=N-N=C functional groups. This π-conjugated system enables electronic excitation in the visible and near-ultraviolet regions. This is of particular interest for many applications, such as corrosion inhibition dye-sensitized solar cells (DSSC), organogels, and fluorescent probes for analytical testing. In addition, many hydrazine derivatives show notable biological and therapeutic activities such as the treatment of tuberculosis, Parkinson’s disease, and hypertension. Schiff bases form a remarkable class of ligands because of their unique properties, such as stability under different conditions, diversity of donor sites, the flexibility of synthesis, and formation of ranges in various coordination geometries in a wide range of complexes. Their complexes have received widespread attention due to their wide range of applications, such as catalysis, electrochemistry, biological sciences, optics, guest chemistry, and molecular recognition. Therefore, from theoretical and practical points of view, the synthesis of hydrazine derivatives is an important issue. In the present study, we describe a new, efficient, and environmentally benign synthetic method for the formation of hydrazine derivatives with heterogeneous catalysis starting from ketones. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 524 KiB

Open AccessProceeding Paper

Comparative Study of the Effects of Aqueous Micellar Media Formed by Amphiphilic Ionic Liquids and Conventional Surfactants on Reactions of Synthetic Interest

by Jésica B. Soffietti, Claudia G. Adam and Claudia Della Rosa

Chem. Proc. 2022, 8(1), 89; https://doi.org/10.3390/ecsoc-25-11745 - 14 Nov 2021

Viewed by 769

Abstract

For polar Diels–Alder (DA) reactions, one of the most relevant aspects is its dependence on the reaction media; thus, in this work, the objective is to analyze the effect of aqueous micellar systems on the synthesis of compounds of biological interest. Based on [...] Read more.

For polar Diels–Alder (DA) reactions, one of the most relevant aspects is its dependence on the reaction media; thus, in this work, the objective is to analyze the effect of aqueous micellar systems on the synthesis of compounds of biological interest. Based on the system formed by isoprene and 2-nitrofuran, the experiments were carried out in micellar media formed by amphiphilic ionic liquid (N,N-dodecylmethylimidazolium bromide) and by conventional surfactants (SDS and CTAB). In this sense, there are few studies that involve DA reactions in micro-heterogeneous systems. The challenge is to have the knowledge about the behavior of ILs in order to take advantage of all their potentialities in order to replace a toxic molecular solvent with ILs, which allows the development of a methodology framed within the concepts of Green Chemistry. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 894 KiB

Open AccessProceeding Paper

Anion Colorimetric Chemosensor Based on a Benzimidazole-Functionalized BODIPY Derivative

by Raquel C. R. Gonçalves, Sónia C. S. Pinto, Susana P. G. Costa and Maria Manuela M. Raposo

Chem. Proc. 2022, 8(1), 90; https://doi.org/10.3390/ecsoc-25-11754 - 18 Jul 2022

Cited by 3 | Viewed by 1377

Abstract

A BODIPY derivative bearing a benzimidazole unit at position 2 and an electron donor group (anthracene) at the meso position was synthetized and characterized by the usual spectroscopic techniques. The evaluation of the compound as a colorimetric chemosensor was performed in solutions of [...] Read more.

A BODIPY derivative bearing a benzimidazole unit at position 2 and an electron donor group (anthracene) at the meso position was synthetized and characterized by the usual spectroscopic techniques. The evaluation of the compound as a colorimetric chemosensor was performed in solutions of acetonitrile/water (75:25) in the presence of several anions (HSO₄⁻, NO₃⁻, H₂PO₄⁻, CN⁻, BzO⁻, ClO₄⁻, Br⁻, F⁻, I⁻ and CH₃CO₂⁻) with biomedical and environmental relevance. The investigated BODIPY derivative demonstrated a selective color change from pink to yellow upon interaction with a hydrogen sulfate anion (HSO₄⁻). Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1219 KiB

Open AccessProceeding Paper

Synthesis and Characterization of a Water-Soluble Pentamethine Indocyanine Dye for Peptide Labeling

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

Chem. Proc. 2022, 8(1), 91; https://doi.org/10.3390/ecsoc-25-11768 - 18 Jul 2022

Viewed by 2260

Abstract

A water-soluble pentamethine cyanine dye was synthesized for further conjugation with peptides. The dye preparation was accomplished by solution-phase chemistry and the synthesized compounds were characterized by the usual techniques (nuclear magnetic resonance, UV-vis absorption and fluorescence spectroscopies and mass spectrometry). The photophysical [...] Read more.

A water-soluble pentamethine cyanine dye was synthesized for further conjugation with peptides. The dye preparation was accomplished by solution-phase chemistry and the synthesized compounds were characterized by the usual techniques (nuclear magnetic resonance, UV-vis absorption and fluorescence spectroscopies and mass spectrometry). The photophysical properties of cyanine 4 were studied in aqueous media, namely in phosphate-buffered saline (PBS) at pH 7.4. Sulfo-Cy5 carboxylic acid 4 exhibited a narrow absorption band and a high molar extinction coefficient (log ε = 5.11) at 646 nm. The wavelength of maximum fluorescence was found in the near-infrared (NIR) region at 661 nm. Therefore, due to its excellent spectral proprieties, good water solubility and emission in the NIR region, dye 4 can be employed in the synthesis of fluorescence resonance energy transfer (FRET) probes for studying enzymatic hydrolysis in vitro. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 2148 KiB

Open AccessProceeding Paper

Solvatochromic Behavior of Polarity Indicators in PILs and Their Mixtures with Molecular Solvents: Autoprotolysis and Its Relation to Acidity

by Claudia Guadalupe Adam, Lucía Gamba and Maria Virginia Bravo

Chem. Proc. 2022, 8(1), 92; https://doi.org/10.3390/ecsoc-25-11746 - 14 Nov 2021

Viewed by 1162

Abstract

It is interesting to know the behavior of Protic Ionic Liquids (PILs) within the binary mixture of molecular solvents, since it is usual to carry out processes such as organic and inorganic synthesis, or liquid–liquid extractions in the presence of another solvent. Moreover, [...] Read more.

It is interesting to know the behavior of Protic Ionic Liquids (PILs) within the binary mixture of molecular solvents, since it is usual to carry out processes such as organic and inorganic synthesis, or liquid–liquid extractions in the presence of another solvent. Moreover, on certain occasions, the absence of water is strictly required. In this sense, it is important to note that the addition of small amounts of IL to the molecular solvent allows a fine adjustment in its microscopic properties, obtaining “new solvent systems” with particular properties. The solvatochromic dyes are traditionally used as microscopic descriptors to determine the molecular microscopic properties of solvents, so we aim to re-evaluate the behavior of these probes and reconsider the validity of traditional polarity scales such as E_T(30) in alkylammonium-based PILs, as well as in their mixtures with molecular solvents, knowing that the real composition of these PILs depends on the equilibrium of autoprotolysis. The characterization of systems was completed in terms of a change in the ∆pKa of the precursor species of a PIL. A thermal analysis was also employed to determine the acid strength’s role in an ion’s complete formation in pure PILs. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 357 KiB

Open AccessProceeding Paper

Hybrid Molecules Based on Fullerene C₆₀ and Spiropyrans as a Promising Approach to the Creation of Anticancer Drugs

by Artur A. Khuzin, Liliya L. Khuzina, Airat R. Tuktarov and Usein M. Dzhemilev

Chem. Proc. 2022, 8(1), 93; https://doi.org/10.3390/ecsoc-25-11656 - 13 Nov 2021

Viewed by 833

Abstract

In this work, we present a novel spiropyran–containing photochromic pyrrolidinofullerene as a promising agent for the photodynamic therapy of cancer. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 5825 KiB

Open AccessProceeding Paper

Synthesis of 2-aminopyridine Lactones and Studies of Their Antioxidant, Antibacterial and Antifungal Properties

by Fadila Salhi, Nawel Cheikh, Didier Villemin and Nathalie Bar

Chem. Proc. 2022, 8(1), 94; https://doi.org/10.3390/ecsoc-25-11709 - 15 Nov 2021

Cited by 1 | Viewed by 825

Abstract

In the present work, the synthesis and biological activities of substituted 2-aminopyridine δ-lactone derivatives were achieved. 4,6,6-trimethyl-2-oxo-5,6-dihydro-2H-pyran-3-carbonitrile was synthesised from 4-hydroxy-4-methylpentan-2-one, followed by its transformation in enaminonitrile with DMFDMA. The antioxidant effects of substituted 2-aminopyridine δ-lactone derivatives were evaluated through DPPH assay and [...] Read more.

In the present work, the synthesis and biological activities of substituted 2-aminopyridine δ-lactone derivatives were achieved. 4,6,6-trimethyl-2-oxo-5,6-dihydro-2H-pyran-3-carbonitrile was synthesised from 4-hydroxy-4-methylpentan-2-one, followed by its transformation in enaminonitrile with DMFDMA. The antioxidant effects of substituted 2-aminopyridine δ-lactone derivatives were evaluated through DPPH assay and revealed a great antioxidant capacity. The antifungal and antibacterial activities were investigated by disc diffusion method against clinical Gram-negative bacteria and against clinical fungi. The study shows moderate to very good antibacterial and antifungal activities for the new substituted 2-aminopyridine δ-lactone derivatives. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 395 KiB

Open AccessProceeding Paper

Covalent Binding of C₆₀ Fullerene to Quadricyclanes A Synthetic Avenue to Hexamethanofullerenes with Promising Antitumor Activity

by Arslan Akhmetov, Zarema Sadretdinova, Lilya U. Dzhemileva, Airat Tuktarov and Usein Dzhemilev

Chem. Proc. 2022, 8(1), 95; https://doi.org/10.3390/ecsoc-25-11649 - 13 Nov 2021

Viewed by 801

Abstract

The Bingel–Hirsch reaction was used to synthesize two new hexamethanofullerenes containing six quadricyclane fragments. Preliminary experiments have established that the synthesized compounds have a high antitumor effect in combination with cisplatin on human T-lymphoblastic leukemia cells (Jurkat cells). Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 383 KiB

Open AccessProceeding Paper

Fullerenyl-1,2,3-Triazoles: Synthesis and Cytotoxic Activity

by Zarema R. Sadretdinova, Arslan R. Akhmetov, Lilya U. Dzhemileva, Vladimir A. D’yakonov, Airat Tuktarov and Usein Dzhemilev

Chem. Proc. 2022, 8(1), 96; https://doi.org/10.3390/ecsoc-25-11659 - 13 Nov 2021

Viewed by 747

Abstract

Through the reaction of fullerenylazide with terminal acetylenes, previously undescribed 1-butyl-2-triazolylfullerenes, in which the heterocyclic fragment was directly attached to the fullerene backbone, were synthesized for the first time. Water-soluble complexes of the synthesized adducts of fullerene with polyvinylpyrrolidone showed a high cytotoxic [...] Read more.

Through the reaction of fullerenylazide with terminal acetylenes, previously undescribed 1-butyl-2-triazolylfullerenes, in which the heterocyclic fragment was directly attached to the fullerene backbone, were synthesized for the first time. Water-soluble complexes of the synthesized adducts of fullerene with polyvinylpyrrolidone showed a high cytotoxic activity towards tumor cells of the Jurkat, K562, and U937 lines. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 989 KiB

Open AccessProceeding Paper

Effective Synthesis of a Novel Betulinic Acid Conjugate with Mitochondria-Targeting Cation F16

by Darya Nedopekina, Eldar Davletshin and Anna Spivak

Chem. Proc. 2022, 8(1), 97; https://doi.org/10.3390/ecsoc-25-11638 - 12 Nov 2021

Viewed by 1239

Abstract

Currently, mitochondria are considered as an attractive universal target in the development of new anticancer drugs. These organelles are essential in energy production, the regulation of cell death pathways, the generation of reactive oxygen species, as well as in the maintenance of calcium [...] Read more.

Currently, mitochondria are considered as an attractive universal target in the development of new anticancer drugs. These organelles are essential in energy production, the regulation of cell death pathways, the generation of reactive oxygen species, as well as in the maintenance of calcium homeostasis. Various approaches are being developed to deliver biologically active compounds into the mitochondria of tumour cells, including the conjugation of cytotoxic substances with mitochondria-targeted lipophilic cations. Among the currently known low molecular weight lipophilic cationic molecules, (E)-4(1H-indol-3-ylvinyl)-N-methylpyridinium iodide (F16) is of great interest. This mitochondria-toxic cationic compound with luminescent properties is selectively accumulated in mitochondria and can selectively trigger the apoptosis and necrosis of tumour cells, making it an attractive targeted agent for theranostic use. Meanwhile, betulinic acid, an available natural pentacyclic triterpenoid, has been considered as a promising scaffold for the development of new anticancer agents in recent years. The antitumour effect of this natural product arises from it affecting the mitochondria of tumour cells through the formation of reactive oxygen species. The present article details of an efficient synthesis of a novel multifunctional hybrid agent in which a cytotoxic triterpenoid, betulinic acid, is carbon-carbon bonded to the cationic F16 fragment at the C-2 position of ring A through a phenylethynyl spacer. The starting substrates in the synthesis were the C-2 propynyl derivative of betulinic acid and N-aryl-substituted 4-(1H-indol-3-ylvinyl)-pyridine. The derivative of betulinic acid with a terminal acetylenic group was prepared by the reaction of C-alkylation with propargyl bromide of potassium enoxytriethylborate generated from betulonic acid. To obtain the N-aryl-substituted analogue of F16, a CuI-catalyzed Ullmann-Goldberg reaction was applied. The synthesis of the target conjugate was successfully completed by the cross-coupling of the terpene and heterocyclic components according to Sonogashira in the presence of the CuI/Pd(PPh₃)₂ catalyst. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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10 pages, 1254 KiB

Open AccessProceeding Paper

Is the Impact of Ethylammonium Nitrate on Soil Basal Respiration Modified by Addition of Aluminium Salt to Improve the Performance in Electrochemical Applications?

by Teresa Sixto, María Eugenia Priano, Juan J. Parajó and Carmen Trasar-Cepeda

Chem. Proc. 2022, 8(1), 98; https://doi.org/10.3390/ecsoc-25-11789 - 14 Nov 2021

Viewed by 847

Abstract

Interest in the possible use of EAN in electronic devices has increased in recent years. EAN can be used directly as an electrolyte, but its application could potentially be optimized by mixing with a metal salt such as Al(NO₃)₃. [...] Read more.

Interest in the possible use of EAN in electronic devices has increased in recent years. EAN can be used directly as an electrolyte, but its application could potentially be optimized by mixing with a metal salt such as Al(NO₃)₃. Although ionic liquids (ILs) have been considered to cause little harm because they are non-volatile, they can have toxic effects on the terrestrial environment. In this study, the impact on soil basal respiration of EAN alone, a mixture of EAN and Al(NO₃)₃, and Al(NO₃)₃ alone was investigated using two soils with different organic matter contents. The Al(NO₃)₃ did not affect soil respiration in either soil, while EAN, either alone or mixed with Al(NO₃)₃ affected both soils. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 1092 KiB

Open AccessProceeding Paper

Synthesis and Biological Activity of New Derivatives of Isoindoline-1,3-dione as Non-Steroidal Analgesics

by Yulia A. Trukhanova, Denis A. Kolesnik, Elena V. Kuvaeva, Galina V. Ksenofontova, Marina V. Sopova and Igor P. Yakovlev

Chem. Proc. 2022, 8(1), 99; https://doi.org/10.3390/ecsoc-25-11773 - 14 Nov 2021

Cited by 1 | Viewed by 1522

Abstract

A simple method for the synthesis of new derivatives of isoindoline-1,3-dione is developed in this study, which consists of the interaction of N-arylbenzenecarboximidamides with phthalic anhydride in benzene at reflux. It was found that carrying out the reaction without heating leads to [...] Read more.

A simple method for the synthesis of new derivatives of isoindoline-1,3-dione is developed in this study, which consists of the interaction of N-arylbenzenecarboximidamides with phthalic anhydride in benzene at reflux. It was found that carrying out the reaction without heating leads to the formation of monoacylation products—phthalic acid amides. The structure of the isolated substances was proved using ¹H and ¹³C NMR spectroscopy. Acute toxicity and biological activity in silico were studied for all of the obtained compounds using the online programs GUSAR and PASS. For 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione and 2-((phenyl(phenylimino)methyl)carbamoyl)benzoic acid, an acute toxicity and biological activity in vivo was studied in laboratory mice. It was shown that the results of in silico and in vivo methods are comparable and indicate the low toxicity of the obtained compounds. It was revealed that 2-(phenyl(phenylimino)methyl)isoindoline-1,3-dione has a high analgesic activity, 1.6 times higher than the activity of the reference drug metamizole sodium. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1376 KiB

Open AccessProceeding Paper

Investigation of Interactions of ortho- and para-N-Aryl-Substituted 2-Trifluoromethylcinnamanilides

by Dominika Pindjakova, Lucia Vrablova, Tomas Strharsky, Jiri Kos and Josef Jampilek

Chem. Proc. 2022, 8(1), 100; https://doi.org/10.3390/ecsoc-25-11651 - 13 Nov 2021

Viewed by 756

Abstract

Unsubstituted (2E)-N-phenyl-3-[2-(trifluoromethyl)phenyl]prop-2-enamide and six other ortho- or para-halogen-substituted anilides of 2-(trifluoromethyl)cinnamic acid were prepared. As the benzene nucleus of cinnamic acid itself is substituted in C₍₂₎ position with a trifluoromethyl moiety that is spatially close to [...] Read more.

Unsubstituted (2E)-N-phenyl-3-[2-(trifluoromethyl)phenyl]prop-2-enamide and six other ortho- or para-halogen-substituted anilides of 2-(trifluoromethyl)cinnamic acid were prepared. As the benzene nucleus of cinnamic acid itself is substituted in C₍₂₎ position with a trifluoromethyl moiety that is spatially close to both the amide bond and the halogen (F, Cl, CF₃) ortho-substitution of the anilide ring, interesting intramolecular interactions can be expected. Other derivatives are substituted at the para-position of the anilide ring, so that intermolecular interactions can be expected. Thus, it can be assumed that predicted properties, especially lipophilicity, will differ significantly from experimentally determined values. All the discussed compounds were analyzed using the reversed-phase high-performance liquid chromatography method. The procedure was performed under isocratic conditions with methanol as an organic modifier in the mobile phase using an end-capped non-polar C18 stationary reversed-phase column. In the present study, the structure–lipophilicity relationships of the studied compounds are discussed. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1062 KiB

Open AccessProceeding Paper

Carbon Dots Synthesis from Coffee Grounds, and Sensing of Nitroanilines

by Bianca Moraes, Alexandra I. Costa, Patrícia D. Barata and José V. Prata

Chem. Proc. 2022, 8(1), 101; https://doi.org/10.3390/ecsoc-25-11777 - 14 Nov 2021

Viewed by 1300

Abstract

Fluorescent carbon dots (C-dots) were directly synthesized by a sustainable and ecofriendly one-pot microwave-assisted hydrothermal carbonization method from coffee grounds waste. The coffee grounds obtained from automatic coffee machines, after being heated at 190 °C for 1–4 h in the presence of nitrogen [...] Read more.

Fluorescent carbon dots (C-dots) were directly synthesized by a sustainable and ecofriendly one-pot microwave-assisted hydrothermal carbonization method from coffee grounds waste. The coffee grounds obtained from automatic coffee machines, after being heated at 190 °C for 1–4 h in the presence of nitrogen additives, furnished the desired carbon nanomaterials. Structural and photophysical properties of the as-synthesized nanomaterials were evaluated by FTIR, ¹H NMR, UV-Vis, and fluorescence spectroscopies. The ability of the C-dots to behave as probes for isomeric nitroanilines (ortho-, meta- and para-nitroaniline) was explored through fluorimetric titration experiments. High sensitivities and selectivities were obtained for the detection of nitroanilines in aqueous media. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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8 pages, 1277 KiB

Open AccessProceeding Paper

Amide-Stabilized Enols in the Enol-Ugi Reaction: A Five-Component Synthesis of Triamides

by Ana G. Neo, M. Teresa G. Castellano, José L. Ramiro and Carlos F. Marcos

Chem. Proc. 2022, 8(1), 102; https://doi.org/10.3390/ecsoc-25-11665 - 13 Nov 2021

Cited by 1 | Viewed by 1074

Abstract

In continuation with our research in the use of enols in multicomponent reactions with isocyanides (IMCR), for the first time we have used amide-stabilized enols as the acid component in enol-Ugi reactions. Thus, the reaction of 2-(hydroxy(phenylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione with aldehydes, amines and isocyanides provides [...] Read more.

In continuation with our research in the use of enols in multicomponent reactions with isocyanides (IMCR), for the first time we have used amide-stabilized enols as the acid component in enol-Ugi reactions. Thus, the reaction of 2-(hydroxy(phenylamino)methylene)-5,5-dimethylcyclohexane-1,3-dione with aldehydes, amines and isocyanides provides the expected enamine adducts. On the other hand, the use of analogous Meldrum’s acid-derived enols permits the synthesis of triamides by a five-component process with the participation of a molecule of solvent. These results confirm the great potential of the enol-Ugi reaction for the preparation of a wide variety of structures containing a peptidomimetic scaffolds. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 894 KiB

Open AccessProceeding Paper

Synthesis, Insecticidal Activity and Nanoencapsulation Studies of Alkoxy Alcohols from Eugenol

by Catarina M. M. Coelho, Maria José G. Fernandes, David M. Pereira, Renato B. Pereira, A. Gil Fortes, M. Sameiro T. Gonçalves and Elisabete M. S. Castanheira

Chem. Proc. 2022, 8(1), 103; https://doi.org/10.3390/ecsoc-25-11788 - 14 Nov 2021

Viewed by 889

Abstract

The synthesis of three alkoxy alcohols with different chains was carried out from eugenol oxirane. These derivatives were evaluated against their effect on the viability of the insect cell line Sf9 (Spodoptera frugiperda). The molecules under study displayed mild-cytotoxic activity towards [...] Read more.

The synthesis of three alkoxy alcohols with different chains was carried out from eugenol oxirane. These derivatives were evaluated against their effect on the viability of the insect cell line Sf9 (Spodoptera frugiperda). The molecules under study displayed mild-cytotoxic activity towards insect cells, equivalent to the commercial insecticide chlorpyrifos. Nanoencapsulation studies of the most active compound against Sf9 were performed using liposomes of egg-phosphatidylcholine containing 30% cholesterol. The encapsulation efficiency is around 93%, and the release profile for 24 h follows a Korsmeyer–Peppas model. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 1869 KiB

Open AccessProceeding Paper

Synthesis, Characterization and Preliminary Antibacterial Evaluation against Staphylococcus aureus of a New 2,4,5-Tri(hetero)arylimidazole Derivative Based on Azaindole Heterocycle

by Nuna L. P. Ramos, Rui Oliveira, Susana P. G. Costa and Maria Manuela M. Raposo

Chem. Proc. 2022, 8(1), 104; https://doi.org/10.3390/ecsoc-25-11781 - 14 Nov 2021

Viewed by 1297

Abstract

Imidazole derivatives are known for their varied biological applications, such as antibacterial, antifungal, antioxidant, antiviral, antiparasitic and anticancer compounds, among others. Therefore, numerous imidazole derivatives have been synthesized and developed in recent years as potential drugs in the treatment of several diseases. In [...] Read more.

Imidazole derivatives are known for their varied biological applications, such as antibacterial, antifungal, antioxidant, antiviral, antiparasitic and anticancer compounds, among others. Therefore, numerous imidazole derivatives have been synthesized and developed in recent years as potential drugs in the treatment of several diseases. In this communication, we report the synthesis of a new imidazole derivative, substituted at positions 2, 4 and 5 with heterocyclic groups, using a simple synthetic methodology and an easy purification procedure. The new compound was characterized by the usual spectroscopic techniques (NMR, UV-Vis absorption and emission). The evaluation of the novel imidazole derivative as a potential antibiotic drug was carried out against the Gram-positive bacterium Staphylococcus aureus, using the disk test diffusion method. The results showed a dose–response effect against the bacterium under study, revealing that the rational design of this imidazole derivative is quite promising to improve the antibacterial activity of imidazole derivatives. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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4 pages, 1048 KiB

Open AccessProceeding Paper

Cytotoxicity Studies of Eugenol Amino Alcohols Derivatives

by Cláudia Teixeira, Nuno F. S. Pinto, David M. Pereira, Renato B. Pereira, Maria José G. Fernandes, Elisabete M. S. Castanheira, António Gil Fortes and Maria Sameiro T. Gonçalves

Chem. Proc. 2022, 8(1), 105; https://doi.org/10.3390/ecsoc-25-11689 - 14 Nov 2021

Viewed by 899

Abstract

Eugenol is a phenylpropanoid displaying a wide range of biological activities. In this study, the cytotoxic activity of various β-amino alcohols derivatives from eugenol was evaluated in AGS (gastric cancer) and A549 (lung cancer) cell lines. The results show that some structural modifications [...] Read more.

Eugenol is a phenylpropanoid displaying a wide range of biological activities. In this study, the cytotoxic activity of various β-amino alcohols derivatives from eugenol was evaluated in AGS (gastric cancer) and A549 (lung cancer) cell lines. The results show that some structural modifications resulted in enhanced cytotoxic activity towards cancer cells. In addition, the activation of caspase-3 and hence apoptosis induced by these molecules, was also explored. Considering the obtained results, some structure/activity relationships can be drawn, which may guide future structural improvements for anticancer agents. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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7 pages, 2102 KiB

Open AccessProceeding Paper

Synthesis of 4′-Alkoxy-4-(ω-cinnamoylalkoxy)azobenzenes and Their Photoswitchable Behavior

by Abdullah Al-Hemyari, Muna Bufaroosha and Thies Thiemann

Chem. Proc. 2022, 8(1), 106; https://doi.org/10.3390/ecsoc-25-11685 - 14 Nov 2021

Viewed by 915

Abstract

In search of new thermotropic, photoswitchable materials, a number of 4′-alkoxy-4-(ω-cinnamoylalkoxy)azobenzenes were prepared. The synthetic procedure included O-alkylation of 4-nitrophenol, followed by reduction of the nitro group (H₂, Pd/C), diazotization of the aniline, and subsequent reaction with ω-hydroxyalkoxybenzenes, followed by [...] Read more.

In search of new thermotropic, photoswitchable materials, a number of 4′-alkoxy-4-(ω-cinnamoylalkoxy)azobenzenes were prepared. The synthetic procedure included O-alkylation of 4-nitrophenol, followed by reduction of the nitro group (H₂, Pd/C), diazotization of the aniline, and subsequent reaction with ω-hydroxyalkoxybenzenes, followed by a modified Appel-type esterification (BrCCl₃, PPh₃). The photochemical behavior of the substances was investigated. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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6 pages, 739 KiB

Open AccessProceeding Paper

Identification of Vitamin D₃ Hydroxylated Metabolites in Solanum glaucophyllum Leaves: Towards Its Biosynthetic Pathway Elucidation

by María Alejandra Sequeira, Marcos J. Lo Fiego, Juan Daniel Coria, María Julia Castro and María Belén Faraoni

Chem. Proc. 2022, 8(1), 107; https://doi.org/10.3390/ecsoc-25-11686 - 14 Nov 2021

Viewed by 1051

Abstract

Solanum glaucophyllum is a species of the Solanaceae family that causes enzootic calcinosis by vitamin D₃ intoxication in breeding cattle grazing in Argentina. Inspired by thrusting forward the study of the biosynthetic pathway of vitamin D₃ in S. glaucophyllum, the [...] Read more.

Solanum glaucophyllum is a species of the Solanaceae family that causes enzootic calcinosis by vitamin D₃ intoxication in breeding cattle grazing in Argentina. Inspired by thrusting forward the study of the biosynthetic pathway of vitamin D₃ in S. glaucophyllum, the aim of the present work is to provide knowledge of vitamin D₃ toxicity related to concentration in the mentioned species located throughout the Río Salado basin. We present the development of a reverse-phase high-performance liquid chromatography (RP-HPLC) method for the analysis of vitamin D₃ and its hydroxylated metabolites. An exhaustive optimization of the RP-HPLC method allowed us to perform calcitriol (1α,25-(OH)₂D₃) and calcidiol (25-OHD₃) identification, both metabolites obtained by the chemical hydrolysis of S. glaucophyllum leaves starting from its hydrophilic extract. These results allow the design of a monitoring scheme for S. glaucophyllum, achieving a more selective control of this weed to avoid cattle decline in the Río Salado basin. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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5 pages, 387 KiB

Open AccessProceeding Paper

Investigation of the Effect of Selected Piperazine-2,5-Diones on Cartilage-Related Cells

by Josef Jampilek, Jan Hosek and Pavel Bobal

Chem. Proc. 2022, 8(1), 108; https://doi.org/10.3390/ecsoc-25-11650 - 13 Nov 2021

Viewed by 832

Abstract

Various chronic inflammatory diseases have become a problem, especially in the Western world. Whether it concerns inflammation of visceral organs, joints, bones, etc., it is always a physiological reaction of the body, which always tries to eradicate harmful substances and restore tissue homeostasis. [...] Read more.

Various chronic inflammatory diseases have become a problem, especially in the Western world. Whether it concerns inflammation of visceral organs, joints, bones, etc., it is always a physiological reaction of the body, which always tries to eradicate harmful substances and restore tissue homeostasis. Unfortunately, prolonged or chronic inflammation often results in damage to the affected tissues. Diseases such as osteoarthritis, rheumatoid arthritis, and arthrosis, as well as cartilage damage, are very common. In addition to suppressing inflammation in the joints and around the cartilage, it is advantageous to administer compounds that are capable of stimulating cartilage growth and regenerating damaged tissue. Variously substituted piperazine-2,5-dione derivatives were investigated as compounds with a potential effect on cartilage regeneration. A series of assays were performed to evaluate their cytotoxicity, anti-inflammatory activity, and ability to potentiate chondrocyte proliferation and suppress synovial cell growth. The compounds proved to be completely non-toxic for all used types of cells up to the concentration of 20 µM. Unfortunately, their evaluated biological activity proved to be insignificant based on the comparison with untreated cells. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

7 pages, 2117 KiB

Open AccessProceeding Paper

Study of Diels–Alder Reactions of Purpurogallin Tetraacetate with Various Dienophiles

by Salima Dib, Bachir Mostefa-Kara, Didier Villemin and Nathalie Bar

Chem. Proc. 2022, 8(1), 109; https://doi.org/10.3390/ecsoc-25-11707 - 14 Nov 2021

Viewed by 1053

Abstract

Purpurogallin or (6E,8Z)-2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one is a benzotropolone possessing a dienic system and known to inhibit the TLR1/TLR2 activation pathway. We have recently described the easy green synthesis of purpurogallin from pyrogallol catalyzed by a copper complex or by vegetable oxidases. [...] Read more.

Purpurogallin or (6E,8Z)-2,3,4,6-tetrahydroxy-5H-benzo[7]annulen-5-one is a benzotropolone possessing a dienic system and known to inhibit the TLR1/TLR2 activation pathway. We have recently described the easy green synthesis of purpurogallin from pyrogallol catalyzed by a copper complex or by vegetable oxidases. The purpurogallin was acetylated and the tetra-acetate derivative thus obtained was engaged in a Diels–Alder reaction with various dienophiles (benzoquinone, maleic anhydride, ethylmaleimide, phenylmaleimide, etc.). The results obtained are presented and discussed. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 336 KiB

Open AccessProceeding Paper

New Synthesis of Imidazo[1,2-a]pyrimidines Catalyzed Using Gold Nanoparticles

by Djamila Benzenine, Zahira Kibou, Amina Berrichi, Redouane Bachir and Noureddine Choukchou-Braham

Chem. Proc. 2022, 8(1), 110; https://doi.org/10.3390/ecsoc-25-11690 - 14 Nov 2021

Viewed by 1139

Abstract

Heterocyclic compounds are abundant in natural products and bioactive compounds and play a huge role in the present repertoire of medicinal chemists due to their potential capability to modulate physicochemical properties. As a result, chemists have focused their efforts on the functionalization of [...] Read more.

Heterocyclic compounds are abundant in natural products and bioactive compounds and play a huge role in the present repertoire of medicinal chemists due to their potential capability to modulate physicochemical properties. As a result, chemists have focused their efforts on the functionalization of heterocycles. Nitrogen-containing fused heterocyclic compounds are important organic molecules. They are found in a variety of natural products, medicinal compounds and functional materials as structural fragments. The imidazo[1,2-a]pyrimidine skeleton is one of them, and it is linked to the pharmacological activity of related drugs. Anticancer activity medicines, anxiolytic drugs and anti-inflammatory activity pharmaceuticals all have this structural pattern. Many of them have biological, antifungal, antimicrobial, antiviral and anxiolytic properties, which are used in medications such as divaplon and fasiplon. This invention of a new approach to manufacturing 2-arylsubstituted imidazo[1,2-a]pyrimidines efficiently piqued our interest, given the powerful bioactivities of molecules with an imidazopyrimidine core. As a result, appropriate methods for manufacturing such molecules remain appealing. In this context, we would like to present a feasible green chemistry approach for the synthesis of 2-phenyl-imidazo[1,2-a]pyrimidines. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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3 pages, 573 KiB

Open AccessProceeding Paper

Radziszewski-Type Oxidation of 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles

by Polina G. Dahno, Arina G. Levchenko and Victor V. Dotsenko

Chem. Proc. 2022, 8(1), 111; https://doi.org/10.3390/ecsoc-25-11790 - 31 Oct 2022

Viewed by 1170

Abstract

Due to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles are prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with the simultaneous epoxidation and formation of epoxyamides. We found that the reaction proceeds in a non-selective way and yields [...] Read more.

Due to the presence of two acrylonitrile fragments, 3,5-di(α-cyanostyryl)-1,2,4-thiadiazoles are prone to react under Radziszewski reaction conditions (oxidative hydrolysis of nitriles to amides) with the simultaneous epoxidation and formation of epoxyamides. We found that the reaction proceeds in a non-selective way and yields a mixture of products of regioisomeric oxidation. Only in one case we succeeded to isolate the product of double epoxidation. The structure of the epoxyamides products was confirmed by IR and NMR spectroscopy data. Full article

(This article belongs to the Proceedings of The 25th International Electronic Conference on Synthetic Organic Chemistry)

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