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

• Published in: Tropical Journal of Pharmaceutical Research
• Main Author: Abbasi M.A.; Islam M.; Aziz-ur-Rehman; Rasool S.; Rubab K.; Hussain G.; Ahmad I.; Ashraf M.; Shahid M.; Shah S.A.A.
• Format: Article
• Language: English
• Published: University of Benin 2016
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-84962385188&doi=10.4314%2ftjpr.v15i3.22&partnerID=40&md5=68aa30fb5598e85b168cb7bc53343725

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. © Pharmacotherapy Group, Faculty of Pharmacy, University of Benin, Benin City, 300001 Nigeria. All rights reserved.