Synthesis and evaluation of antibacterial and antifungal activities of 4-thiazolidinones and 2-azetidinones derivatives from chalcone

Abstract

(E)-3-(thiophen-2-yl)-1-(4-methylphenyl)-prop-2-en-1-one 1 was obtained from the reaction of thiophene-2-aldehyde with p-methyl acetophenone. The treatment of 1 with guanidine nitrate produced 4-thiophen-2-yl-6-(4-methylphenyl)-pyrimidin-2-ylamine 2. The synthesis of N-substituted benzylidine-4-(4-methylphenyl)-6-(thiophen-2-yl) pyrimidin-2-amines 3a–j was performed by the treatment of compound 2 with the corresponding aromatic aldehydes. The reaction of 3a–j with thioglycolic acid and thiolactic acid formed the corresponding 3-[4-(4-methyl-phenyl)-6-thiophen-2-yl-pyrimidin-2-yl]-2-(substituted-phenyl)-thiazolidin-4-ones 4a–j and 3-[4-(4-methyl-phenyl)-6-thiophen-2-yl-pyrimidin-2-yl]-2-(substituted-phenyl)-5-methyl-thiazolidin-4-ones 5a–j and with chloroacetylchloride, it gives 3-chloro-1-[4-(4-methyl-phenyl)-6-thiophen-2-yl-pyrimidin-2-yl]-4-(substituted-phenyl)-azetidin-2-ones 6a–j. Newer analogues were characterized by infrared spectrum, 1H nuclear magnetic resonance, 13C nuclear magnetic resonance spectroscopy and elemental analyses. The newly synthesized analogues were then examined for their antimicrobial activity against some bacterial and fungal strains as two Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa), two Gram-positive bacteria (Staphylococcus aureus, Streptococcus pyogenes) and two fungal species (Candida albicans, Aspergillus niger, Aspergillus Clavatus) to develop a novel class of antimicrobial agents.