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 2β-methyl group into the 1-oxacephem nucleus increased the stability...

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Published inJournal of antibiotics Vol. 43; no. 4; pp. 357 - 371
Main Authors OKONOGI, TSUNEO, SHIBAHARA, SEIJI, MURAI, YASUSHI, YOSHIDA, TAKASHI, INOUYE, SHIGEHARU, KONDO, SHINICHI, CHRISTENSEN, BURTON G.
Format Journal Article
LanguageEnglish
Published Tokyo JAPAN ANTIBIOTICS RESEARCH ASSOCIATION 1990
Japan Antibiotics Research Association
Subjects
Antibacterial agents
Antibiotics. Antiinfectious agents. Antiparasitic agents
Bacteria - drug effects
Biological and medical sciences
Cephalosporins - chemical synthesis
Cephalosporins - pharmacology
Chemical Phenomena
Chemistry
Medical sciences
Molecular Structure
Pharmacology. Drug treatments
Antibacterial agent
Chemical synthesis
In vitro
Biological activity
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Summary: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 2β-methyl group into the 1-oxacephem nucleus increased the stability to β-laetamases. OCP-9-176 (7b) having the (l-methylpyridinium-4-yl)thiomethyl group at C-3 showed potent antibacterial activity and a broad spectrum.
Bibliography:ObjectType-Article-1
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ISSN:0021-8820
1881-1469
DOI:10.7164/antibiotics.43.357