Synthesis, Characterization, Antibacterial, α-Glucosidase Inhibition and Hemolytic Studies on Some New N-(2,3- Dimethylphenyl)benzenesulfonamide Derivatives

  • Muhammad A. Abbasi
  • Mudassar Islam
  • Aziz-ur Rehman
  • Shahid Rasool
  • Kaniz Rubab
  • Ghulam Hussain
  • Irshad Ahmad
  • Muhammad Ashraf
  • Muhammad Shahid
  • Syed Adnan Ali Shah
Keywords: 2, 3-Dimethylaniline, Antibacterial activity, Anti-enzymatic activity, α-Glucosidase inhibitor, Hemolytic activity, Sulfonamides

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.

Keywords: 2,3-Dimethylaniline, Antibacterial activity, Anti-enzymatic activity, α-Glucosidase inhibitor, Hemolytic activity, Sulfonamides

Published
2016-04-08
Section
Articles

Journal Identifiers


eISSN: 1596-9827
print ISSN: 1596-5996