Synthesis, antibacterial and lipoxygenase inhibition studies on some N-(4-{[(alkyl/aralkyl)(phenethyl)amino]sulfonyl}phenyl) acetamides

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.