Synthetic N-aralkylated-N-(2,4-dimethylphenyl)benzenesulfonamides: As potent anti-bacterial agents

• Published in: Journal of the Chemical Society of Pakistan
• Main Author: Siddiqui S.Z.; Sarwar A.; Abbasi M.A.; Aziz-Ur-Rehman; Hussain M.; Irshad M.; Shah S.A.A.
• Format: Article
• Language: English
• Published: Chemical Society of Pakistan 2016
• Online Access: https://www.scopus.com/inward/record.uri?eid=2-s2.0-85009833752&partnerID=40&md5=220f3fef835255e93a46f0bfe6e8753b

The current research effort embodies the assessment of anti-bacterial potential of some N-substituted sulfonamides. The synthetic methodology was triggered by reaction of 2,4-dimethylaniline (1) with benzenesulfonyl chloride (2) at pH 9-10 in aqueous sodium carbonate (10 %) to generate N-(2,4-dimethylphenyl)benzenesulfonamide (3) which was further treated with different aralkylated halides (4a-e) in polar aprotic medium; N, N-dimethylformamide (DMF) and lithium hydride (LiH) which acts as base under stirring at room temperature for 3 hours to afford N-aralkylated-N-(2,4-dimethylphenyl)benzenesulfonamides (5a-e). The proposed structures of sulfonamides were explicated via contemporary spectral methods e.g. IR, 1H-NMR, 13C-NMR and EIMS. Moreover, they were analyzed against different Gram (-) and (+) bacterial strains to unravel their inhibitory potential. The amalgamation of sulfonamide moiety with different aralkyl halides resulted in good anti-bacterial activity compared to standard; Ciprofloxacin. N-2-bromobenzyl-N-(2,4-dimethylphenyl)benzenesulfonamide (5d) and N-2-phenylpropyl-N-(2,4-dimethylphenyl)benzenesulfonamide (5b) contributed significantly which may be attributed to the successful and fruitful N-insertion of 2-bromobenzyl and 2-phenylpropyl moieties on parent sulfonamide. © 2016, Chemical Society of Pakistan. All rights reserved.