Abstract
The research endeavor was aimed to synthesize N-alkyl/aralkylated-N-(4-ethoxyphenyl)2,3-dihydrobenzo-[1,4]-dioxine-6-sulfonamides and to evaluate their enzyme inhibitory potential. The target molecules were synthesized in two steps. The first step involved the reaction of 4-ethoxyaniline (1) with N-2,3-dihydrobenzo[1,4]-dioxin-6-sulfonyl chloride (2) under dynamic pH control maintained by 10% aqueous Na2CO3 to yield N-(4-ethoxyphenyl)-2,3-dihydrobenzo-[1,4]dioxine-6-sulfonamide (3). In second step parent compound 3 was reacted with various alkyl/aralkyl halides (4a-l) in N,N' -dimethylformamide and catalytic amount of lithium hydride to accomplish some new N-alkyl/aralkylated- N-(4-ethoxyphenyl)-2,3-dihydrobenzo-[1,4]-dioxine-6-sulfonamides (5a-l). Probable structures of the synthesized compounds were characterized by contemporary spectral techniques i.e. IR, H-1-NMR and EIMS and were finally evaluated for enzyme inhibitory potential against alpha-glucosidase and urease. The synthesized compounds exhibited moderate to weak therapeutic potential throughout the series.