Synthesis and Antidiabetic Activity of Novel Molecules Containing p-Aminobenzoic Acid and Benzenesulfonamide Moiety

doi:10.6023/cjoc201204016

Abstract

A new class of target molecules containing p-aminobenzoic acid and benzenesulfonamide moiety is reported, based on the structural features of a series of analogues with strong biological activities previously synthesized by the group. By taking 4 discrete synthetic routes, the practical procedures and facile preparative routes for both the intermediates of IM1～IM3 and the target molecules of TM1 and TM2 were established. A total of 26 designed compounds were synthesized smoothly using the established synthetic approaches under mild reaction conditions, with low cost and high yields (64%～95%). The chemical structures of 21 new compounds were confirmed by ¹H NMR, ¹³C NMR and HRMS techniques. The bioassay test demonstrates weak antidiabetic activity for all the target molecules. This study has further expanded the application of alcohol/SOCl₂ system in the deacylation of N-arylacetamides and chloro-N-arylacetamides as well as esterification of carboxy group concomitantly, which is supportive to the structure optimization of novel molecules containing p-aminobenzoic acid and benzenesulfonamide moiety.

Key words: diabetes mellitus; p-aminobenzoic acid, sulfanilamide, peroxisome proliferator-activated receptors (PPAR), synthesis, activity

Cite this article

Yang Long, Yan Jufang, Fan Li, Chen Xin, Shangguan Ruiyan, Wang Linfa, Yang Dacheng. Synthesis and Antidiabetic Activity of Novel Molecules Containing p-Aminobenzoic Acid and Benzenesulfonamide Moiety[J]. Chin. J. Org. Chem., 2012, 32(10): 1908-1918.

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