Chiang Mai Journal of Science

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Synthesis and Biological Evaluation of Sulfamoyl Carboxamide Derivatives from Sulfur-containing α-Amino acids

Melford C. Egbujor, Uchechukwu C. Okoro, Attah S. Egu, Vivian I. Okonkwo, Sunday N. Okafor, Chigbundu N. Emeruwa, Pius I. Egwuatu, Odera R. Umeh, Mercy I. Eziafakaego, Ifeanyi S. Amasiatu and David C. Nwobodo
* Author for corresponding; e-mail address: nwobododave@gmail.com, egbujormc@gmail.com
Volume: Vol.49 No.4 (July 2022)
Research Article
DOI: https://doi.org/10.12982/CMJS.2022.070
Received: 8 March 2022, Revised: 21 May 2022, Accepted: 25 May 2022, Published: -

Citation: Egbujor M.C., Okoro U.C., Egu A.S., Okonkwo V.I., Okafor S.N., Emeruwa C.N., et al., Synthesis and biological evaluation of sulfamoyl carboxamide derivatives from sulfur-containing α-amino acids, Chiang Mai Journal of Science, 2022; 49(4): 1100-1115. DOI 10.12982/CMJS.2022.070.

Abstract

    A series of new sulfamoyl carboxamide analogs were synthesized using sulfur-containing amino acids and sulfonyl chloride. The characterization of the compounds was done using FTIR, 1H-NMR, 13C-NMR, and elemental analysis. Their antioxidant, antimalarial, antimicrobial activities and molecular docking were evaluated. Compounds 5h (MIC, 0.3, 0.5, 0.3 and 0.4 mg/mL) was the most potent antibacterial agent against Staphylococcus aureus, Escherichia coli, Bacillus subtilis and Salmonella typhi, compounds 5a (MIC, 0.7 mg/mL) and 5g (MIC, 0.7m g/mL) were most potent against Pseudomonas aeruginosa while compound 5e (MIC, 0.5 and 0.8 mg/mL) had the best in vitro antifungal activity against Aspergillus niger and Candida albicans. Compound 5d (1C50 = 1.128 μg/mL) displayed an antioxidant activity comparable with ascorbic acid (1C50 = 1.000 μg/mL) and compound 5e (4, 14, 4%) effected the most significant reduction in the percentage malaria parasitaemia comparable with artemeter lumefantrin (5, 4, 4%) after 5 days of treatment of the mice. From the molecular docking results, compound 5c had a strong molecular interaction with the appropriate drug target, Escherichia coli DNA gyrase complexed with 1-ethyl-3-[8-methyl-5-(2-methyl-pyridin-4-yl) isoquinolin-3-yl]urea (PDB code: 5MMN). The title compounds displayed signifi cant antimicrobial, antioxidant and antimalarial activities.

Keywords: antimalarial, antimicrobial, antioxidant, carboxamide, sulphonamide, methionine, cysteine, molecular docking

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