Synthesis and antibacterial activity of some imidazole-5-(4H)one derivatives

In the present study, several substituted oxazolones were synthesized by condensation of benzoylglycine with different aldehydes. From such oxazolones, substituted imidazolones were synthesized by condensation with ethylenediamine, urea and 4-N,N-dimethylaminoaniline. All these synthesized compounds produced significant antibacterial activities. Furthermore, compounds containing -CH(2)CH(2)NH(2), -CONH(2) and -C(6)H(4)-N(CH(3))(2) groups as substitutents on the imidazolones were found to be potent antibacterial agents. Thus, among the twelve compounds, 1-(2-aminoethyl)-2-phen yl-4-(4-(dimethylamino)benzylidene)imidazole-5-(4H)one (4d), 1-carboxamido-2-phenyl-4-(4-(dimethylamino)benzylidene)imidazole-5-(4H)one (4e) and 1-(4-(N,N-dimethylamino)phenyl)-2-phenyl-4-(4-(dimethylamino)benzylidene)imidazole-5-(4H)one (4f) were found to have a significant higher antibacterial activity than the other substituted imidazolones. Compound 4e was the most active one in this series.