Synthesis and antibacterial activity of novel 2-methyl-1-oxacephalosporins

J Antibiot (Tokyo). 1990 Apr;43(4):357-71. doi: 10.7164/antibiotics.43.357.

Abstract

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 2 beta-methyl group into the 1-oxacephem nucleus increased the stability to beta-lactamases. OCP-9-176 (7b) having the (1-methylpyridinium-4-yl)thiomethyl group at C-3 showed potent antibacterial activity and a broad spectrum.

MeSH terms

  • Bacteria / drug effects*
  • Cephalosporins / chemical synthesis*
  • Cephalosporins / pharmacology
  • Chemical Phenomena
  • Chemistry
  • Molecular Structure

Substances

  • Cephalosporins
  • L 656575