Synthesis and activity of 3-(isoxazolin-5-yl)- and 3-(isoxazol-4-yl)cephalosporins

Y Koyama; S P Huang; D Ikeda; S Kondo; T Takeuchi

doi:10.7164/antibiotics.45.1930

Synthesis and activity of 3-(isoxazolin-5-yl)- and 3-(isoxazol-4-yl)cephalosporins

J Antibiot (Tokyo). 1992 Dec;45(12):1930-8. doi: 10.7164/antibiotics.45.1930.

Authors

Y Koyama¹, S P Huang, D Ikeda, S Kondo, T Takeuchi

Affiliation

¹ Institute of Microbial Chemistry, Tokyo, Japan.

PMID: 1490886
DOI: 10.7164/antibiotics.45.1930

Abstract

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.

MeSH terms

Anti-Bacterial Agents / chemical synthesis*
Anti-Bacterial Agents / pharmacology
Cephalosporins / chemical synthesis*
Cephalosporins / pharmacology
Gas Chromatography-Mass Spectrometry
Gram-Negative Bacteria / drug effects
Gram-Positive Bacteria / drug effects
Isoxazoles / chemical synthesis*
Isoxazoles / pharmacology
Magnetic Resonance Spectroscopy
Microbial Sensitivity Tests

Substances

Anti-Bacterial Agents
Cephalosporins
Isoxazoles