Design, synthesis and biological evaluation of azithromycin glycosyl derivatives as potential antibacterial agents

Bioorg Med Chem Lett. 2013 Sep 15;23(18):5057-60. doi: 10.1016/j.bmcl.2013.07.042. Epub 2013 Jul 25.

Abstract

A series of 11,12-cyclic carbonate azithromycin-4″-O-carbamoyl glycosyl derivatives were designed, synthesized, and evaluated as antibacterial agents to search for target compounds with excellent activity. The results of preliminary antibacterial tests against eight strains in vitro revealed that all of the title compounds exhibited improved activities with broad spectrum compared with the parent compound. The glycosylated side chains may be the pharmacophores responsible for the improved activity.

Keywords: Antibacterial activity; Azithromycin; Glycosyl; Synthesis.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology*
  • Azithromycin / chemical synthesis
  • Azithromycin / chemistry
  • Azithromycin / pharmacology*
  • Dose-Response Relationship, Drug
  • Drug Design*
  • Escherichia coli / drug effects*
  • Glycosylation
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Staphylococcus / drug effects*
  • Structure-Activity Relationship

Substances

  • Anti-Bacterial Agents
  • Azithromycin