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ORIGINAL ARTICLE
Year : 2022  |  Volume : 17  |  Issue : 1  |  Page : 99-110

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


1 Department of Industrial Chemistry, Renaissance University, Ugbawka, Enugu State, Nigeria
2 Synthetic Organic Chemistry Division, Department of Pure and Industrial Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria
3 Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, Nsukka, Enugu State, Nigeria
4 Department of Pure and Industrial Chemistry, Kogi State University, Anyigba, Kogi State, Nigeria
5 Department of Biochemistry, Renaissance University, Ugbawka, Enugu State, Nigeria
6 Department of Microbiology, Renaissance University, Ugbawka, Enugu State, Nigeria
7 Department of Applied Microbiology and Brewing, Nnamdi Azikiwe University, P.M.B 5025 Awka, Anambra State, Nigeria

Correspondence Address:
Melford C Egbujor
Department of Industrial Chemistry, Renaissance University, Ugbawka, Enugu State
Nigeria
Sunday N Okafor
Department of Pharmaceutical and Medicinal Chemistry, University of Nigeria, Nsukka, Enugu State
Nigeria
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Source of Support: None, Conflict of Interest: None


DOI: 10.4103/1735-5362.329930

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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.


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