STUDIES ON ORALLY ACTIVE CEPHALOSPORINS: II. SYNTHESIS AND STRUCTURE-ACTIVITY RELATIONS OF NEW [(E) OR (Z) 3-SUBSTITUTED CARBAMOYLOXY]-1-PROPENYL CEPHALOSPORINS

In an effort to find a new oral cephalosporin with well-balanced antibacterial spectrum, good oral absorbability and long plasma half-life, a series of oxyimino aminothiazolyl 3-[(E)- or (Z)-N-substituted carbamoyloxy]propenyl cephems was synthesized and evaluated for antibacterial activity and oral...

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Bibliographic Details
Published in:Journal of antibiotics 1994/12/25, Vol.47(12), pp.1526-1540
Main Authors: NEGI, SHIGETO, SASHO, MANABU, YAMANAKA, MOTOSUKE, SUGIYAMA, ISAO, KOMATSU, YUKI, TSURUOKA, AKIHIKO, KAMADA, ATSUSHI, TSUKADA, ITARU, HIRUMA, RYOICHI, KATSU, KANEMASA, MACHIDA, YOSHIMASA
Format: Article
Language:English
Subjects:
Administration, Oral
Animals
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Biological and medical sciences
Biological Availability
Cephalosporins - administration & dosage
Cephalosporins - chemistry
Cephalosporins - pharmacology
Magnetic Resonance Spectroscopy
Male
Medical sciences
Mice
Mice, Inbred ICR
Microbial Sensitivity Tests
Pharmacology. Drug treatments
Structure-Activity Relationship
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Summary:In an effort to find a new oral cephalosporin with well-balanced antibacterial spectrum, good oral absorbability and long plasma half-life, a series of oxyimino aminothiazolyl 3-[(E)- or (Z)-N-substituted carbamoyloxy]propenyl cephems was synthesized and evaluated for antibacterial activity and oral absorbability. The substituents of the carbamoyloxy group affected their in vitro activity and bioavailability after oral administration of their pivaloyloxymethyl esters at the C-4 position. The compound possessing an N, N-dimethylcarbamoyloxy moiety at the C-3 position showed good oral absorption and well-balanced antibacterial activity. In this report, the structure-activity relationships and the structure-oral absorbability relationships of 3-(N-substituted carbamoyloxy)-propenyl cephems are described.
ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.47.1526