Enzyme Inhibition and In Silico Studies of New Synthetic N-Substituted- (4-Bromophenyl)-4-Ethoxybenzenesulfonamides

Abstract

A series of new N-substituted-(4-bromophenyl)-4-ethoxybenzenesulfonamides (5a-o) were synthesized and evaluated for enzyme inhibition potential. The task was accomplished by the reaction of 4-bromobenzenesulfonyl chloride a. with 4-ethoxyaniline b. to get the intermediate 4-bromophenyl-4-ethoxybenzenesulfonamide in the first step. The compound 3 on further reaction with different electrophiles (4a-o) yielded the target compounds 5a-o, which were characterized with the help of FTIR, 1 H-, 13 C-NMR spectroscopic and EI-MS & HR-EI-MS spectrometric data. These sulfonamides (5a-o) were evaluated for their acetylcholinesterase (AChE) and α -glucosidase inhibitory potential. Compounds 5l, 5n, 5g, 5j and 5h exhibited excellent potential against AChE with IC 50 values of 52.63 ± 0.14, 82.75 ± 0.16, 92.13 ± 0.15, 92.52 ± 0.16 and 98.72 ± 0.12 µM, respectively. Compounds 5h, 5j, 5c, 5d and 5l were found potent inhibitors of α -glucosidase with IC 50 values of 57.38 ± 0.19, 123.36 ± 0.19, 123.42 ± 0.19, 124.35 ± 0.15 and 124.74 ± 0.18 µM, respectively. The activity results were also substantiated by in silico studies.