Synthesis and carbonic anhydrase isoenzymes I and II inhibitory effects of novel benzylamine derivatives

Abstract

Synthesis and carbonic anhydrase inhibitory properties of novel diarylmethylamines 22–25 and sulfonamide derivatives 26–28 were investigated. Acylation of methoxy-substituted benzenes with benzene carboxylic acids, reduction of ketones with NaBH4, conversion of alcohols to azides, Pd-C catalyzed hydrogenation of azides afforded title compounds 22–25. Compounds 22, 24 and 25 were converted to sulfonamide derivatives 26–28 with MeSO2Cl. The inhibitory effects of novel benzylamine derivatives 22–28 were tested on human carbonic anhydrase (hCA, EC 4.2.1.1) isozymes hCA I and II. The results demonstrated that compound 28 was found to be the best inhibitor against both hCA I (Ki: 3.68 µM) and hCA II (Ki: 9.23 µM).