Preparation and antibiotic activity of monobactam analogues of nocardicins

Prep Biochem Biotechnol. 1999 Aug;29(3):257-72. doi: 10.1080/10826069908544928.

Abstract

A series of diverse beta-lactam analogues of nocardicins with interesting antimicrobial properties were prepared. Coupling of glucosamine to these compounds improved their water solubility. Aminoacid derivatives produced a stereoinduction on the quaternary enantiotopic carbon of the starting compound 1. Evaluation of their antimicrobial activity showed that the introduction of alpha-amninoacids to monobactams increased their activity. The importance of asymmetric carbon is exemplified by the higher antibiotic activity of L-alpha-aminoacids than the D-series. No significant difference was observed between fluorinated and non-fluorinated monobactams.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Ampicillin / pharmacology
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Candida albicans / drug effects
  • Chemistry, Pharmaceutical / methods
  • Gram-Negative Bacteria / drug effects*
  • Gram-Positive Bacteria / drug effects*
  • Isomerism
  • Lactams*
  • Magnetic Resonance Spectroscopy
  • Microbial Sensitivity Tests
  • Models, Chemical
  • Monobactams / chemical synthesis*
  • Monobactams / chemistry
  • Monobactams / pharmacology*
  • Penicillins / pharmacology

Substances

  • Anti-Bacterial Agents
  • Lactams
  • Monobactams
  • Penicillins
  • nocardicin
  • Ampicillin