title: Synthesis and antibacterial activity of novel 2-methyl-1-oxacephalosporins.
abstract: New 2-methyl-1-oxacephem compounds having 2-(2-aminothiazol-4-yl)-2-(alkoxyimino)acetamido substituents at C-7 and various C-3 side chains were synthesized starting from (3R,4S)-phenyloxazolinoazetidinone (8). Introduction of the 2 beta-methyl group into the 1-oxacephem nucleus increased the stability to beta-lactamases. OCP-9-176 (7b) having the (1-methylpyridinium-4-yl)thiomethyl group at C-3 showed potent antibacterial activity and a broad spectrum.
authors.affiliation: Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
authors.forename: T
authors.initials: T
authors.lastname: Okonogi
authors.forename: S
authors.initials: S
authors.lastname: Shibahara
authors.forename: Y
authors.initials: Y
authors.lastname: Murai
authors.forename: T
authors.initials: T
authors.lastname: Yoshida
authors.forename: S
authors.initials: S
authors.lastname: Inouye
authors.forename: S
authors.initials: S
authors.lastname: Kondo
authors.forename: B G
authors.initials: BG
authors.lastname: Christensen
mesh_terms: D001419:Bacteria / Q000187:drug effects*; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D015394:Molecular Structure
chemical_list: D002511:Cephalosporins; C057304:L 656575