Synthesis and antibacterial activity of novel 2-methyl-1-oxacephalosporins.
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.
Okonogi
T
T
Pharmaceutical Research Center, Meiji Seika Kaisha, Ltd., Yokohama, Japan.
Shibahara
S
S
Murai
Y
Y
Yoshida
T
T
Inouye
S
S
Kondo
S
S
Christensen
B G
BG
D001419:Bacteria / Q000187:drug effects*; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D055598:Chemical Phenomena; D002621:Chemistry; D015394:Molecular Structure
D002511:Cephalosporins; C057304:L 656575