Facile, highly efficient, and clean one-pot synthesis of acridine sulfonamide derivatives at room temperature and their inhibition of human carbonic anhydrase isoenzymes

Abstract

Reaction of dimedone, 4-amino-N-(diamino- methylene)benzenesulfonamide, and aromatic aldehydes was successfully realized using sulfuric acid as a cheap catalyst. Synthesis of novel acridine sulfonamide compounds was performed providing high yields in water as the solvent at room temperature. This method has several advantages such as use of a green solvent, high yields, and efficient one-pot procedure. In addition, human carbonic anhydrase isoenzymes (hCA I and hCA II) were purified from erythrocyte cells by affinity chromatography. The inhibi- tory effects of acetazolamide and the newly synthesized acridine sulfonamides on hydratase and esterase activities of these isoenzymes was studied in vitro. The esterase IC50 values of the new compounds are 47.2-230.1 lM for hCA I and 50.1-275.0 lM for hCA II.