Synthesis, Spectral Characterization and Biological Screening of N-Substituted Derivatives of N-(1-Hydroxy-2-methylpropan-2-yl)benzenesulfonamide

Abstract

In the present study, a series of N-substituted derivative of N-(1-hydroxy-2-methylpropan-2-yl)benzenesulfonamide was synthesized. Firstly, the reaction of 2-amino-2-methyl propan-1-ol (1) with benzenesulfonyl chloride (2) yielded N-(1-hydroxy-2-methylpropan-2-yl)benzene sulfonamide (3) and secondly on treatment with different electrophiles (4a-i) in the presence of N,N-dimethyl formamide and sodium hydride which act as a base furnished into N-substituted derivatives of N-(1-hydroxy-2-methylpropan-2-yl)benzenesulfonamide (5a-i). All these derivatives along with their parent compounds were characterized by IR, EI-MS and ¹H NMR spectra. These compounds were assayed for their antioxidant activities by using 2,2-diphenyl-1-picrylhydrazil (DPPH) scavenging and other biological activities via screening them against acetylcholinesterase, butyrylcholinesterase and lipoxygenase enzymes, however, these showed prominent activity against butyrylcholinesterase enzyme. It is clearly evident from the results that compounds, N-(butan-2-yl)-N-(1-hydroxy-2-methylpropan-2-yl)benzene sulfonamide (5e) and N-(allyl)-N-(1-hydroxy-2-methylpropan-2-yl)benzenesulfonamide (5f) were found to be potent inhibitor having IC₅₀ value of 65.47 ± 0.69 and 79.36 ± 0.92 μmol, respectively, relative to eserine, a reference standard with IC₅₀ value of 0.85 ± 0.001 μmol. These two compounds 5e and 5f were also showed good scavenging activity against DPPH.