Molecular properties prediction, synthesis, and antimicrobial activity of bis(azolyl)sulfonamidoacetamides

Abstract

A library of bis(azolyl)sulfonamidoacetamides was prepared by the reaction of azolylsulfonylamines with azolylchloroacetamides in the presence of pyridine/4-(dimethylamino)pyridine (DMAP) under ultrasonication. The reaction proceeded well with DMAP, resulting in a higher yield of the products. The antimicrobial activity of the compounds indicated that N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl)amino}-2-oxoethyl)sulfamoyl]-4-phenylthiazol-2-yl}benzamide (22a), N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chlorophenyl)thiazol-2-yl}benzamide (22c), and N-{5-[N-(2-{[4-(4-chloro-1H-pyrrol-2-yl)-1H-imidazol-2-yl]amino}-2-oxoethyl)sulfamoyl]-4-(4-chloro-phenyl)-1H-imidazol-2-yl}benzamide (24c) exhibited a low minimal inhibitory concentration (MIC) against Bacillus subtilis, equal to the standard drug, chloramphenicol. Compounds 22c and 24c also showed low MICs against Aspergillus niger, equal to the standard drug, ketoconazole. The molecular properties of the synthesized molecules were studied to identify druglikeness properties of the target compounds. On the basis of molecular properties prediction, 19a, 19b, 20b, 20c, 21a-c, 22b, 22c, and 23a-c can be treated as drug candidates.

Keywords: antibacterial activity; antifungal activity; bis(azolyl)sulfonamidoacetamides; molecular properties; ultrasonication.