Design, Synthesis, Antimicrobial and Antioxidant Activities of Novel Threonine-based Sulfonamide Derivatives

Aim:To systematically design, synthesize and evaluate the biological activities of new threonine-based sulfonamide derivatives in order to achieve improved drug potency.Methodology: Sulfamoyl carboxylic acidswere prepared by the reaction of threonine with the appropriate sulfonyl chloride while their acetylated, carboxamide and aniline derivatives were synthesized via Lumiere-Barbier acetylation, Schotten-Baumann ammonolysis and Buchwald-Hartwig cross-coupling methods respectively. The FTIR, 1H-NMR, 13C-NMR and elemental analytical data were employed in the structural characterization. In vitro andin silico antioxidant and antimicrobial studies were carried out.Results:Compounds 1b and 1d displayed thebest in vitro antibacterial activities againstEscherichia coli, Salmonella typhi, Staphylococcus aureus, Bacillus subtilis, Pseudomonas aeruginosa, and antifungal activities against Candida albicansandAspergillus niger. Compound 1f (IC50= 1.150±0.003μg/ml) exhibited the best in vitro antioxidant activity. Compound 1a had a higherin silicoantibacterial (-11.51 kcal/mol) binding energies than antibacterial reference drug, penicillin (-10.89 kcal/mol). Compound 1c had the highest in silicoantifungal binding energy (-10.48kcal/mol)comparable to ketoconazole(-10.85 kcal/mol). Conclusion: All the compounds were found to be potential antioxidant and antimicrobial drug candidates having complied with Lipinski’s rule of five.

Keywords

Threonine, sulfonamides, In silico, antimicrobial, antioxidant

Citation

Egbujor M. C., Okoro U. C., Nwobodo D.C., Ezeagu C.U., Amadi U.B., Okenwa-Ani C. G., Ugwu J.I., Okoye I.G., Abu I.P., Egwuatu P. I.. Design, Synthesis, Antimicrobial and Antioxidant Activities of Novel Threonine-based Sulfonamide Derivatives. Journal of Pharmaceutical Research International. 2020 May; 32(8): 51-61

URI

https://imsear.searo.who.int/handle/123456789/215736

Collections

Journal of Pharmaceutical Research International

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