Synthetic N-Alkyl/aralkyl-4-methyl-N-(naphthalen-1-yl)benzenesulfonamides as Potent Antibacterial Agents

Abstract

The current research effort involved the reaction of napthalen-1-amine (1) with 4-methylbenzenesulfonyl chloride (2) under dynamic pH control at 9-10, maintained with 10% aqueous Na2CO3 to obtain 4-methyl-N-(naphthalen-1-yl) benzenesulfonamide (3). The parent molecule 3 was further substituted at N-atom with alkyl/aralkyl halides (4a-f) in polar aprotic solvent; N,Ndimethylformamide, and lithium hydride which acts as a base, to achieve N-alkyl/aralkyl-4-methyl-N-(naphthalen-1yl)benzenesulfonamides (5a-f). All the synthesized compounds were structurally elucidated by IR, H-NMR and EIMS spectral techniques. All the derivatives were further screened for antibacterial and anti-enzymatic potential against various bacterial strains and enzymes, respectively, and were found to be potent antibacterial agents and moderate to weak enzyme inhibitors.