Substituted isoxazole analogs of farnesoid X receptor (FXR) agonist GW4064

Bioorg Med Chem Lett. 2009 Jun 1;19(11):2969-73. doi: 10.1016/j.bmcl.2009.04.047. Epub 2009 Apr 18.

Abstract

Starting from the known FXR agonist GW 4064 1a, a series of alternately 3,5-substituted isoxazoles was prepared. Several of these analogs were potent full FXR agonists. A subset of this series, with a tether between the isoxazole ring and the 3-position aryl substituent, were equipotent FXR agonists to GW 4064 1a, with the 2,6-dimethyl phenol analog 1t having greater FRET FXR potency than GW 4064 1a.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Fluorescence Resonance Energy Transfer
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology
  • Rats
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / metabolism
  • Structure-Activity Relationship

Substances

  • Isoxazoles
  • Receptors, Cytoplasmic and Nuclear
  • farnesoid X-activated receptor
  • GW 4064