Synthesis of Novel 4-Thiazolidinones as Antibacterial Agents

Abstract

Amino function of 2-Amino-1,3,4-thiadiazole-5-thiol (1) has been diazotized by hydrochloric acid and sodium nitrite. The generating thiadiazolyldiazonium chloride was directly reacted with sodium phenoxide of salicylaldehyde affording azo copound (2) that containing aldehyde function. Compound (2) has been condensed with aromatic amines (3-nitroaniline, 2-nitroaniline, 4-aminophenol, 3-aminophenol, and 2-aminophenol utilizing microwave method in ethyl alcohol to give the imine compounds (3a-3e), correspondingly. Cyclization reaction of Schiff bases (3a-3e) and a mercaptoacetic acid usage microwave method in dimethylformamide gave easy thiazolidin-4-one derivatives (4a-4e), respectively. Antibacterial activities of 4-thiazolidinone compounds were tested using Gram-positive and Gram-negative bacteria. The outcomes indicated that thiazolidinone derivatives (4c, 4d, and 4e) possess greater activity against Gram-positive bacteria comparing to standard antibiotic (amoxicillin-clavulanate), whereas derivatives (4c and 4e) appeared better impact than the control drug athwart Gram-negative germs.