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 (K_i: 3.68 µM) and hCA II (K_i: 9.23 µM).

• Benzylamine
• carbonic anhydrase
• enzyme inhibition
• sulfonamide