Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents

Background and purpose: The preponderance of microbial infections remains a global challenge. In the present study, synthesis of novel cysteine-based antimicrobial agents and their biological evaluation is reported. Experimental approach: The reaction of p-toluenesulphonyl chloride with cysteine aff...

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Autores principales:	Melford C Egbujor, Uchechukwu C Okoro, Sunday N Okafor, Samuel A Egu, Ifeanyi S Amasiatu, Pius I Egwuatu, Odera R Umeh, Eziafakaego M Ibo
Formato:	article
Lenguaje:	EN
Publicado:	Wolters Kluwer Medknow Publications 2022
Materias:	antimicrobial activity; carboxamide; cysteine; molecular docking; sulphonamide. Pharmacy and materia medica RS1-441
Acceso en línea:	https://doaj.org/article/0d64314ccf004a3fa80c7ece308bcf91
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spelling	oai:doaj.org-article:0d64314ccf004a3fa80c7ece308bcf912021-11-19T12:17:04ZDesign, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents1735-53621735-941410.4103/1735-5362.329930https://doaj.org/article/0d64314ccf004a3fa80c7ece308bcf912022-01-01T00:00:00Zhttp://www.rpsjournal.net/article.asp?issn=1735-5362;year=2022;volume=17;issue=1;spage=99;epage=110;aulast=Egbujorhttps://doaj.org/toc/1735-5362https://doaj.org/toc/1735-9414Background and purpose: The preponderance of microbial infections remains a global challenge. In the present study, synthesis of novel cysteine-based antimicrobial agents and their biological evaluation is reported. Experimental approach: The reaction of p-toluenesulphonyl chloride with cysteine afforded 2-{[(4-methylphenyl)sulphonyl]amino}-3-sulphanylpropanoic acid [3] which was acetylated based on Lumiere-Barbier method using acetic anhydride. The ammonolysis of the acetylated compound [4] gave the carboxamide derivative [5] which reacted with aniline, aminopyridine and diaminopyrimidine via nickel catalyzed Buchwald-Hartwig amidation reaction to afford compounds 6a, 6b, and 6c, respectively. The compounds were characterized using FTIR, 1H-NMR, 13C-NMR, and elemental analysis. The in vitro antimicrobial activities were determined. Their physicochemical properties were generated in silico and the molecular docking studied bacterial and fungal infections. Findings/Results: Compounds 4, 6b, and 6c exhibited excellent in vitro antibacterial activities while compound 4 had the best antifungal activities. From the in silico antimicrobial results, compound 3 had a better binding affinity (-10.95 kcal/mol) than penicillin (-10.89 kcal/mol) while compounds 3 and 4 had binding affinities (-10.07 and -10.62kcal/mol) comparable to ketoconazole (-10.85 kcal/mol). Conclusion and implication: All the synthesized compounds exhibited significant antibacterial and antifungal activities and were confirmed to be potential antimicrobial agents.Melford C EgbujorUchechukwu C OkoroSunday N OkaforSamuel A EguIfeanyi S AmasiatuPius I EgwuatuOdera R UmehEziafakaego M IboWolters Kluwer Medknow Publicationsarticleantimicrobial activity; carboxamide; cysteine; molecular docking; sulphonamide.Pharmacy and materia medicaRS1-441ENResearch in Pharmaceutical Sciences, Vol 17, Iss 1, Pp 99-110 (2022)
institution	DOAJ
collection	DOAJ
language	EN
topic	antimicrobial activity; carboxamide; cysteine; molecular docking; sulphonamide. Pharmacy and materia medica RS1-441
spellingShingle	antimicrobial activity; carboxamide; cysteine; molecular docking; sulphonamide. Pharmacy and materia medica RS1-441 Melford C Egbujor Uchechukwu C Okoro Sunday N Okafor Samuel A Egu Ifeanyi S Amasiatu Pius I Egwuatu Odera R Umeh Eziafakaego M Ibo Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
description	Background and purpose: The preponderance of microbial infections remains a global challenge. In the present study, synthesis of novel cysteine-based antimicrobial agents and their biological evaluation is reported. Experimental approach: The reaction of p-toluenesulphonyl chloride with cysteine afforded 2-{[(4-methylphenyl)sulphonyl]amino}-3-sulphanylpropanoic acid [3] which was acetylated based on Lumiere-Barbier method using acetic anhydride. The ammonolysis of the acetylated compound [4] gave the carboxamide derivative [5] which reacted with aniline, aminopyridine and diaminopyrimidine via nickel catalyzed Buchwald-Hartwig amidation reaction to afford compounds 6a, 6b, and 6c, respectively. The compounds were characterized using FTIR, 1H-NMR, 13C-NMR, and elemental analysis. The in vitro antimicrobial activities were determined. Their physicochemical properties were generated in silico and the molecular docking studied bacterial and fungal infections. Findings/Results: Compounds 4, 6b, and 6c exhibited excellent in vitro antibacterial activities while compound 4 had the best antifungal activities. From the in silico antimicrobial results, compound 3 had a better binding affinity (-10.95 kcal/mol) than penicillin (-10.89 kcal/mol) while compounds 3 and 4 had binding affinities (-10.07 and -10.62kcal/mol) comparable to ketoconazole (-10.85 kcal/mol). Conclusion and implication: All the synthesized compounds exhibited significant antibacterial and antifungal activities and were confirmed to be potential antimicrobial agents.
format	article
author	Melford C Egbujor Uchechukwu C Okoro Sunday N Okafor Samuel A Egu Ifeanyi S Amasiatu Pius I Egwuatu Odera R Umeh Eziafakaego M Ibo
author_facet	Melford C Egbujor Uchechukwu C Okoro Sunday N Okafor Samuel A Egu Ifeanyi S Amasiatu Pius I Egwuatu Odera R Umeh Eziafakaego M Ibo
author_sort	Melford C Egbujor
title	Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
title_short	Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
title_full	Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
title_fullStr	Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
title_full_unstemmed	Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
title_sort	design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents
publisher	Wolters Kluwer Medknow Publications
publishDate	2022
url	https://doaj.org/article/0d64314ccf004a3fa80c7ece308bcf91
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Design, synthesis, and molecular docking of cysteine-based sulphonamide derivatives as antimicrobial agents

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