Conformationally constrained farnesoid X receptor (FXR) agonists: Naphthoic acid-based analogs of GW 4064

Bioorg Med Chem Lett. 2008 Aug 1;18(15):4339-43. doi: 10.1016/j.bmcl.2008.06.073. Epub 2008 Jun 28.

Abstract

Starting from the known FXR agonist GW 4064 1a, a series of stilbene replacements were prepared. The 6-substituted 1-naphthoic acid 1b was an equipotent FXR agonist with improved developability parameters relative to 1a. Analog 1b also reduced the severity of cholestasis in the ANIT acute cholestatic rat model.

MeSH terms

  • Administration, Oral
  • Animals
  • Carboxylic Acids / chemical synthesis*
  • Carboxylic Acids / chemistry
  • Carboxylic Acids / pharmacology*
  • Cholestasis / drug therapy*
  • Cholestasis / metabolism
  • Cholestasis / pathology
  • Crystallography, X-Ray
  • DNA-Binding Proteins / agonists*
  • DNA-Binding Proteins / chemistry
  • Disease Models, Animal
  • Dogs
  • Gastric Mucosa / metabolism
  • Haplorhini
  • Isoxazoles / chemical synthesis*
  • Isoxazoles / chemistry
  • Isoxazoles / pharmacology*
  • Mice
  • Molecular Conformation
  • Molecular Structure
  • Naphthalenes / chemical synthesis*
  • Naphthalenes / chemistry
  • Naphthalenes / pharmacology*
  • Rats
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / chemistry
  • Stomach / drug effects
  • Structure-Activity Relationship
  • Transcription Factors / agonists*
  • Transcription Factors / chemistry

Substances

  • Carboxylic Acids
  • DNA-Binding Proteins
  • Isoxazoles
  • Naphthalenes
  • Receptors, Cytoplasmic and Nuclear
  • Transcription Factors
  • farnesoid X-activated receptor
  • 1-naphthoic acid
  • GW 4064