Conformationally constrained farnesoid X receptor (FXR) agonists: heteroaryl replacements of the naphthalene

Bioorg Med Chem Lett. 2011 Feb 15;21(4):1206-13. doi: 10.1016/j.bmcl.2010.12.089. Epub 2010 Dec 23.

Abstract

To improve on the drug properties of GSK8062 1b, a series of heteroaryl bicyclic naphthalene replacements were prepared. The quinoline 1c was an equipotent FXR agonist with improved drug developability parameters relative to 1b. In addition, analog 1c lowered body weight gain and serum glucose in a DIO mouse model of diabetes.

MeSH terms

  • Animals
  • Binding Sites
  • Blood Glucose / metabolism
  • Crystallography, X-Ray
  • Diabetes Mellitus, Experimental / metabolism
  • Dogs
  • Fluorescence Resonance Energy Transfer
  • Humans
  • Isoxazoles / chemical synthesis
  • Isoxazoles / chemistry*
  • Isoxazoles / pharmacokinetics
  • Ligands
  • Mice
  • Molecular Conformation
  • Naphthalenes / chemistry*
  • Protein Structure, Tertiary
  • Quinolines / chemical synthesis
  • Quinolines / chemistry*
  • Quinolines / pharmacokinetics
  • Rats
  • Receptors, Cytoplasmic and Nuclear / agonists*
  • Receptors, Cytoplasmic and Nuclear / metabolism
  • Weight Gain / drug effects

Substances

  • Blood Glucose
  • GSK 2324
  • Isoxazoles
  • Ligands
  • Naphthalenes
  • Quinolines
  • Receptors, Cytoplasmic and Nuclear
  • farnesoid X-activated receptor
  • naphthalene