Synthesis and preliminary pharmacological profile of some new 3,5-dihydro-4H-imidazol-4-one and α,β-dehydroamino acid derivatives

Abstract

A new series of 3,5-dihydro-4H-imidazol-4-one derivatives incorporating thiazole moiety have been readily prepared through the nucleophilic acyl substitution reactions of 5(4H)-oxazolones derivatives (2A-2J) with 4-(benzo[d]thiazol-2-yl) aniline (3) using a simple synthetic strategy under mild condition. Furthermore, the ring opening reaction of same components were examined to afford a new series of α,β-dehydroamino acid derivatives (4A-4J) in good yield. The preliminary pharmacological profile of all newly synthesized compounds were evaluated in vitro for their antibacterial and antifungal activities using micro broth dilution assay method, and it was revealed that most of the synthesized derivatives were exhibiting promising pharmacological activities against both strains. The structures of the newly synthesized 3,5- dihydro-4H-imidazol-4-one (5A-5J)) and α,β-dehydroamino acid derivatives (4A-4J) were expounded and elucidated on the bases of their FT-IR, 1H- and 13C –NMR spectral data.

Keywords

• Keywords: Imidazol-4-one, dehydroamino acid, thiazole, acyl substitution, antibacterial, antifungal