Synthesis and biological activity of new 5-O-sugar modified ketolide and 2-fluoro-ketolide antibiotics

Bioorg Med Chem Lett. 2005 Mar 1;15(5):1307-10. doi: 10.1016/j.bmcl.2005.01.027.

Abstract

A series of new triazole-containing ketolides and 2-fluoro-ketolides in which the 5-O-desosamine was replaced by unnatural sugars were synthesized and evaluated against relevant macrolide-sensitive and macrolide-resistant respiratory pathogens. Excellent in vitro antibacterial activities were demonstrated for ketolide analogues having the 6'-OBz-3'-dimethylamino-glucose and 6'-OBz-4'-deoxy-3'-dimethylamino-glucose substituents.

Publication types

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

MeSH terms

  • Amino Sugars / chemistry*
  • Anti-Bacterial Agents* / chemical synthesis
  • Anti-Bacterial Agents* / pharmacology
  • Ketolides* / chemical synthesis
  • Ketolides* / pharmacology
  • Microbial Sensitivity Tests
  • Molecular Conformation
  • Stereoisomerism
  • Structure-Activity Relationship

Substances

  • Amino Sugars
  • Anti-Bacterial Agents
  • Ketolides
  • desosamine