Synthesis and biological investigation of new 4''-malonyl tethered derivatives of erythromycin and clarithromycin

Bioorg Med Chem Lett. 2006 Mar 15;16(6):1506-9. doi: 10.1016/j.bmcl.2005.12.033. Epub 2006 Jan 4.

Abstract

A new approach to 4''-substituted derivatives of erythromycin and clarithromycin was developed by converting them into corresponding 4''-malonic monoesters. Subsequent carbodiimide coupling with alcohols and amines provided new macrolide derivatives that are capable of binding to 50S ribosomal subunits and inhibiting protein synthesis in cell-free system.

Publication types

  • Research Support, N.I.H., Extramural
  • Research Support, Non-U.S. Gov't

MeSH terms

  • Cell-Free System
  • Clarithromycin / analogs & derivatives
  • Clarithromycin / chemical synthesis*
  • Clarithromycin / metabolism
  • Erythromycin / analogs & derivatives
  • Erythromycin / chemical synthesis*
  • Erythromycin / metabolism
  • Protein Synthesis Inhibitors / chemical synthesis
  • Protein Synthesis Inhibitors / metabolism
  • RNA, Ribosomal, 23S / metabolism
  • Ribosomes / drug effects
  • Ribosomes / metabolism*

Substances

  • Protein Synthesis Inhibitors
  • RNA, Ribosomal, 23S
  • Erythromycin
  • Clarithromycin