Precursor-directed syntheses and biological evaluation of new elansolid derivatives

Chembiochem. 2012 Aug 13;13(12):1813-7. doi: 10.1002/cbic.201200228. Epub 2012 Jul 17.

Abstract

The antibiotic elansolid C1 (8) was isolated from Chitinophaga sancti strain FxGBF13 after fermentation in the presence of anthranilic acid. Remarkably, 8 was also obtained by addition of anthranilic acid to a crude fermentation extract containing the macrolide elansolid A2 (1*). This Michael-type conjugate addition allowed us to generate 21 new derivatives of elansolid C1 (9-29) by using various nucleophiles. Biological activities of all derivatives were evaluated against Staphylococcus aureus, Micrococcus luteus, and the mouse cell line L929.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Anti-Bacterial Agents / chemistry
  • Anti-Bacterial Agents / isolation & purification*
  • Anti-Bacterial Agents / pharmacology
  • Bacteria / chemistry
  • Cell Line
  • Cell Survival / drug effects
  • Complex Mixtures / chemistry
  • Drug Evaluation, Preclinical
  • Fermentation
  • Fibroblasts / drug effects*
  • Macrolides / chemistry
  • Macrolides / isolation & purification*
  • Macrolides / pharmacology
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Mice
  • Microbial Sensitivity Tests
  • Micrococcus luteus / drug effects*
  • Micrococcus luteus / growth & development
  • Staphylococcus aureus / drug effects*
  • Staphylococcus aureus / growth & development
  • ortho-Aminobenzoates / chemistry

Substances

  • Anti-Bacterial Agents
  • Complex Mixtures
  • Macrolides
  • elansolid C1
  • ortho-Aminobenzoates
  • anthranilic acid