Synthetic N-aralkylated-N-(2,4-dimethylphenyl)benzenesulfonamides: as potent anti-bacterial agents. | [Journal of Chemical Society of Pakistan • 2016]

Author(s):

1. Sabahat Zahra Siddiqui: Department of Chemistry, Government College University, Lahore, Pakistan

2. Afzaal Sarwar: Department of Chemistry, Government College University, Lahore, Pakistan

3. Muhammad Athar Abbasi: Department of Chemistry, Government College University, Lahore, Pakistan

4. Aziz-Ur-Rehman : Department of Chemistry, Government College University, Lahore, Pakistan

5. Mazhar Hussain: Department of Chemistry, Government College University, Lahore, Pakistan

6. Muhammad Irshad: Department of Pharmacy, The Islamia University of Bahawalpur, Bahawalpur, Pakistan

7. Syed Adnan Ali Shah: Research Institute of Natural Products for Drug Discovery RiND, NMR Facility Division, Faculty of Pharmacy, Universiti Teknologi MARA UiTM, Puncak Alam Campus, Bandar Puncak Alam, Selangor D. E. Malaysia

Abstract:

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 Naralkylated-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.

Page(s): 1151-1158

DOI: DOI not available

Published: Journal: Journal of Chemical Society of Pakistan, Volume: 38, Issue: 6, Year: 2016

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