title: Synthesis and activity of potent 3-(isoxazolidin-5-yl)- and 3-(isoxazolidinium-5-yl)cephalosporins.
abstract: The syntheses and in vitro antibacterial activities of 3-(isoxazolidin-5-yl)- and 3-(isoxazolidinium-5-yl)cephalosporins are described. 1,3-Dipolar cycloaddition of 3-vinylcephalosporin with nitrone gave diastereomeric isomers of 3-(isoxazolidin-5-yl)cephalosporin. The antibacterial activities of 3'-(S)-isomers were superior to those of 3'-(R)-isomers. The quaternarization of isoxazolidine ring increased the antibacterial activity. Among them, compound 10b with a hydroxyimino group in the C-7 side chain showed potent activities against staphylococci and compound 10f with an N-hydroxypyridone exhibited an excellent antipseudomonal activity.
authors: Institute of Microbial Chemistry, Tokyo, Japan.
authors: S P
authors: SP
authors: Huang
authors: Y
authors: Y
authors: Koyama
authors: D
authors: D
authors: Ikeda
authors: S
authors: S
authors: Kondo
authors: T
authors: T
authors: Takeuchi
mesh_terms: D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology*; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology*; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007536:Isomerism; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology*; D009682:Magnetic Resonance Spectroscopy; D013058:Mass Spectrometry; D008826:Microbial Sensitivity Tests; D013055:Spectrophotometry, Infrared
chemical_list: D000900:Anti-Bacterial Agents; D002511:Cephalosporins; D007555:Isoxazoles