Synthesis and activity of 3-(isoxazolin-5-yl)- and 3-(isoxazol-4-yl)cephalosporins.
The 1,3-dipolar cycloaddition of nitrile oxide with 3-vinylcephalosporin provided diastereomeric isomers of 3-(isoxazolin-5-yl)cephalosporin. Cycloaddition of nitrile oxide with 3-(dimethylamino-vinyl)cephalosporin gave 3-(isoxazol-4-yl)cephalosporin. These semisynthetic cephalosporins with an aminothiazole in the C-7 side chain showed moderate antibacterial activities.
Koyama
Y
Y
Institute of Microbial Chemistry, Tokyo, Japan.
Huang
S P
SP
Ikeda
D
D
Kondo
S
S
Takeuchi
T
T
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000494:pharmacology; D002511:Cephalosporins / Q000138:chemical synthesis* / Q000494:pharmacology; D008401:Gas Chromatography-Mass Spectrometry; D006090:Gram-Negative Bacteria / Q000187:drug effects; D006094:Gram-Positive Bacteria / Q000187:drug effects; D007555:Isoxazoles / Q000138:chemical synthesis* / Q000494:pharmacology; D009682:Magnetic Resonance Spectroscopy; D008826:Microbial Sensitivity Tests
D000900:Anti-Bacterial Agents; D002511:Cephalosporins; D007555:Isoxazoles