Synthesis and Biological Studies of Some New N-Substituted Derivatives of N-(1,3-Benzodioxol-5-yl)-4-methylbenzenesulfonamide

Sulfonamides are biologically active compounds with broad spectrum of activities. In the presented research, a small collection of N-alkyl/aralkyl substituted sulfonamides have been synthesized and investigated for inhibition of different bacterial strains. The 1,3-Benzodioxol-5-amine (1) was treated with tosyl chloride (2) in water under mild basic conditions to yield the molecule, N-(1,3-Benzodioxol-5-yl)-4-methylbenzenesulfonamide (3). The target compounds, 5a-i, were obtained by stirring 3 with different electrophiles, 4a-i, in the presence of N,N-dimethylformamide and sodium hydride. The structures of the synthesized compounds were established by spectroscopic techniques like IR, H-1-NMR and EI-MS. These compounds were assayed for their antimicrobial activities via screening against Gram-positive and Gram-negative bacteria. The most of the compounds showed moderate activity against P. aeruginosa relative to reference standard drug, ciprofloxacin.