Synthesis and antimicrobial activity of some new sugar-based monocyclic beta-lactams

Molecules. 2004 Jan 31;9(1):29-38. doi: 10.3390/90100029.

Abstract

The syntheses of some new sugar-based monocyclic beta-lactams possessing several other functionalities in addition to the carbohydrate moiety are described. The key step was the Staudinger [2+2] cycloaddition of chiral carbohydrate Schiff base 5 with phthalimidoacetyl chloride to yield the sugar-based monocyclic beta-lactam 6 as a single isomer. Treatment of protected beta-lactams 6 and 8 with methylhydrazine afforded the free amino beta-lactams 9 and 10. Acylation of these free amino beta-lactams with benzoyl, phenoxyacetyl, cinnamoyl and phenylacetyl chloride in the presence of pyridine afforded beta-lactams 11a-d and 12a-d. Some of these novel beta-lactams were found to be active against Staphilococcus citrus, Klebsiella pneumoniae, Escherichia coli and Bacillus subtilis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / metabolism
  • Carbohydrates / chemistry*
  • Galactose / chemistry
  • Humans
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Molecular Structure
  • Monobactams / chemical synthesis*
  • Monobactams / chemistry
  • Monobactams / metabolism

Substances

  • Anti-Bacterial Agents
  • Carbohydrates
  • Monobactams
  • Galactose