Synthesis and biological activity of novel 3-(2-propenyl)-cephalosporins. I.
The synthesis, antibacterial activity and oral absorption of novel cephalosporins (3a-3d) having a 2-propenyl group at the C-3 position are described. Diphenylmethyl 7-amino-3-(2-propenyl)-3-cephem-4-carboxylate HCl (4) prepared from 7-aminocephalosporanic acid in 12 steps was acylated with various acid moieties to give cephems 3a-3d. The cephems 3a-3c showed similar antibacterial activities as cefixime. However, these cephems were not well absorbed orally.
Kim
W J
WJ
Korea Research Institute of Chemical Technology, Daedeog-Danji, Daejeon.
Ko
K Y
KY
Kim
H
H
Oh
J
J
D000042:Absorption; D000284:Administration, Oral; D000475:Alkenes / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology*; D000818:Animals; D001419:Bacteria / Q000187:drug effects*; D020682:Cefixime; D002439:Cefotaxime / Q000031:analogs & derivatives / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology; D002506:Cephalexin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology; D002511:Cephalosporins / Q000138:chemical synthesis / Q000493:pharmacokinetics / Q000494:pharmacology* / Q000652:urine; D002845:Chromatography; D004353:Drug Evaluation, Preclinical; D007700:Kinetics; D051379:Mice; D008826:Microbial Sensitivity Tests; D015394:Molecular Structure; D051381:Rats
D000475:Alkenes; D002511:Cephalosporins; C028352:cefems; D020682:Cefixime; C013658:propylene; D002439:Cefotaxime; D002506:Cephalexin