Synthesis, characterization, antibacterial, α-glucosidase inhibition and hemolytic studies on some new n-(2,3-Dimethylphenyl)benzenesulfonamide derivatives

Abstract

Purpose: To synthesize a series of new N-(2,3-dimethylphenyl)benzenesulfonamide derivatives with pharmacological analysis. Methods: N-(2,3-Dimethylphenyl)benzenesulfonamide (3) was synthesized by the reaction between 2,3-dimethylaniline (1) and benzenesulfonyl chloride (2) in aqueous basic medium. Compound 3 was further treated with various alkyl/aralakyl halides (4a-m) to yield new compounds, 5a-m, in a weak basic aprotic polar organic medium. The proposed structures of synthesized compounds were confirmed using proton-nuclear magnetic resonance (1H-NMR), infra-red spectroscopy (IR) and electron impact mass spectrometry (EIMS). The synthesized compounds were screened for in vitro antibacterial, antienzymatic and hemolytic activities using standard procedures. Results: All the synthesized compounds showed moderate to high activity against Gram-positive and Gram-negative bacterial strains. The molecules 5g and 5j exhibited good inhibition of α-glucosidase enzyme with half-maximal inhibitory concentration (IC50) of 59.53 ± 0.01 and 55.31 ± 0.01 μmoles/L, respectively, relative to acarbose with IC50 of 38.25 ± 0.12 μmoles/L. All the compounds exhibited cytotoxicity levels ranging from 27.20 ± 0.24 to 5.20 ± 0.41%, relative to Triton X-100. Conclusion: Compound 5f is the most potent antibacterial while 5j is the best α-glucosidase inhibitor; 5e showed the least cytotoxicity.