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.
Saravanan
Sampath
S
Department of Medicinal Chemistry, Nandha College of Pharmacy, Erode, India. saravecp@yahoo.co.in
Selvan
Perumal Senthamil
PS
Gopal
Natesan
N
Gupta
Jayanta Kumar
JK
De
Biplap
B
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D001419:Bacteria / Q000187:drug effects* / Q000254:growth & development; D007093:Imidazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D013329:Structure-Activity Relationship
C507462:1-carboxamido-2-phenyl-4-(4-(dimethylamino)benzylidene)imidazole-5-(4H)one; D000900:Anti-Bacterial Agents; D007093:Imidazoles; C117197:imidazolone