Orally active cephalosporins. II. Synthesis and structure-activity relationships of new 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-cephalospori ns with 1,2,3-triazole in C-3 side chain

J Antibiot (Tokyo). 1993 Jan;46(1):177-92. doi: 10.7164/antibiotics.46.177.

Abstract

The synthesis, antibacterial activity and oral absorbability of 7 beta-[(Z)-2-(2-aminothiazol-4-yl)-2-hydroxyiminoacetamido]-3 -(1H-1,2, 3-triazol-4-yl)thiomethylthio-3-cephem-4-carboxylic acid (1g) and related compounds are described. Their oral absorbability was influenced by the spacer length between C-3 of a cephem nucleus and C-4' of 1,2,3-triazole. The SCH2S structure was also found to contribute to their good oral absorption. The quantitative relationship between the bioavailability and the spacer length of cephalosporins (1a-1n) is discussed.

MeSH terms

  • Absorption
  • Animals
  • Bacteria / drug effects
  • Biological Availability
  • Cephalosporins / chemical synthesis*
  • Cephalosporins / pharmacokinetics
  • Female
  • Macaca fascicularis
  • Magnetic Resonance Spectroscopy
  • Male
  • Mice
  • Mice, Inbred ICR
  • Microbial Sensitivity Tests
  • Mouth Mucosa / metabolism*
  • Spectrophotometry, Infrared
  • Structure-Activity Relationship

Substances

  • Cephalosporins