Original Article

Synthesis, Antibacterial and Lipoxygenase Inhibition Studies on Some N-(4-{[(Alkyl/aralkyl)(phenethyl)amino]sulfonyl}phenyl) acetamides

  • Muhammad A ABBASI
  • Rabia KHIZER
  • Aziz-ur- REHMAN
  • Sabahat Z SIDDIQUI
  • Kaniz RUBAB
  • Rabia MALIK
  • Irshad AHMAD
  • Syed Adnan A. SHAH

Received Date: 06.11.2014 Accepted Date: 26.03.2015 Turk J Pharm Sci 2015;12(3):257-266

In the present study, 2-phenyl-1-ethanamine (phenethyl amine;1) was reacted with 4-acetamido benzenesulfonyl chloride (2) in the presence of 10% aqueous Na2CO3 to achieve N-{4-[(phenethylamino)sulfonyl]phenyl}acetamide (3) which was further reacted with different alkyl/aralkyl halides, 4a-f, in polar aprotic solvent, N,N-dimethylformamide (DMF) and sodium hydride as base to afford various N-substituted derivatives of 3. Structural elucidation of N-{4-[(phenethylamino)sulfonyl] phenyl}acetamide derivatives, 5a-f, was done by IR,1H-NMR and mass spectral analysis. Parent molecule 3, as well as N-substituted derivatives 5a, 5b, 5e and 5f revealed good to moderate antibacterial potential against various Gram-positive and Gram-negative bacterial strains as compared to standard, ciprofloxacin. Moreover, N-­-(4-­-{[(4-­-chlorobenzyl)(phenethyl)amino]sulfonyl}phenyl) acetamide (5c) proved to be a possible inhibitor of lipoxygenase enzyme having IC50 of 135.31±0.81 μM relative to Baicalein which was taken as a reference.

Keywords: Phenethyl amine, 4-acetamidobenzenesulfonyl chloride, Antibacterial activity, Lipoxygenase