Synthesis and antibacterial activity of O-methyl derivatives of azalide antibiotics: I. 4", 11 and 12-OMe derivatives via direct methylation

Bioorg Med Chem Lett. 1998 Mar 3;8(5):549-54. doi: 10.1016/s0960-894x(98)00070-5.

Abstract

A series of O-Me derivatives of 9-deoxo-8a-aza-8a-homoerythromycin has been prepared and evaluated for antibacterial activity. The relative rates of methylation of the four available hydroxyls (4", 6, 11 and 12) in 2',3'-bis-Cbz protected 9-deoxo-8a-aza-8a-homoerythromycin were compared to those given in a published report for the similarly protected 9a-azalide. An incongruity in the results prompted reinvestigation of the O-methylation of the 9a-azalide, and an error in structure assignment in the published report was discovered: the compound reported as the 6-OMe-9a-azalide has been determined to be the 12-OMe derivative.

MeSH terms

  • Anti-Bacterial Agents / chemical synthesis*
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / pharmacology
  • Erythromycin / analogs & derivatives*
  • Erythromycin / chemical synthesis
  • Erythromycin / chemistry
  • Erythromycin / pharmacology
  • Gram-Positive Bacteria / drug effects
  • Kinetics
  • Magnetic Resonance Spectroscopy
  • Methylation
  • Microbial Sensitivity Tests
  • Molecular Structure

Substances

  • Anti-Bacterial Agents
  • Erythromycin
  • 9-deoxy-9a-aza-9a-methyl-9a-homoerythromycin A