Studies on cephalosporin antibiotics. IV. Synthesis, antibacterial activity and oral absorption of new 3-(2-substituted-vinylthio)-7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2- (carboxymethoxyimino)acetamido]cephalosporins.
A series of new 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-(carboxymethoxyimino)ace tamido] cephalosporins (1) having various substituted-vinylthio groups at the C-3 position of the cephen nucleus was synthesized and evaluated for antibacterial activity and oral absorption in rats in comparison with cefixime. Of these, the cephalosporins (1a and 1c) with a lower alkoxycarbonylvinylthio group (Z-form) at the C-3 position showed a potent antibacterial activity against Gram-negative bacteria, improved activity against Staphylococcus aureus as well as good oral absorption in rats. The structure-activity relationships of 1 are also presented.
Yokoo
C
C
Research Center, Taisho Pharmaceutical Co., Ltd., Saitama, Japan.
Goi
M
M
Onodera
A
A
Fukushima
H
H
Nagate
T
T
D000284:Administration, Oral; D000818:Animals; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000493:pharmacokinetics / Q000494:pharmacology; D007408:Intestinal Absorption; D008297:Male; D008826:Microbial Sensitivity Tests; D051381:Rats; D011919:Rats, Inbred Strains; D013329:Structure-Activity Relationship
D002511:Cephalosporins