Dataset Information

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

ABSTRACT:

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.

SUBMITTER: Egbujor MC

PROVIDER: S-EPMC8621839 | biostudies-literature | 2022 Feb

REPOSITORIES: biostudies-literature

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Publications

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

Egbujor Melford C MC Okoro Uchechukwu C UC Okafor Sunday N SN Egu Samuel A SA Amasiatu Ifeanyi S IS Egwuatu Pius I PI Umeh Odera R OR Ibo Eziafakaego M EM

Research in pharmaceutical sciences 20211111 1

<h4>Background and purpose</h4>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.<h4>Experimental approach</h4>The reaction of <i>p</i>-toluenesulphonyl chloride with cysteine afforded 2-{[(4-methylphenyl)sulphonyl]amino}-3-sulphanylpropanoic acid <b>(3)</b> which was acetylated based on Lumiere-Barbier method using acetic anhydride. The ammonolysis of the ...[more]

PMID: 34909048

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Dataset Information

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

Background and purpose

Experimental approach

Findings/results

Conclusion and implication

Publications

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

Similar Datasets

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