Discovery of novel indane derivatives as liver-selective thyroid hormone receptor β (TRβ) agonists for the treatment of dyslipidemia

Bioorg Med Chem. 2012 Jun 1;20(11):3622-34. doi: 10.1016/j.bmc.2012.03.056. Epub 2012 Apr 11.

Abstract

Thyromimetics that specifically target TRβ have been shown to reduce plasma cholesterol levels and avoid atherosclerosis through the promotion of reverse cholesterol transport in an animal model. We designed novel thyromimetics with high receptor (TRβ) and organ (liver) selectivity based on the structure of eprotirome (3) and molecular modeling. We found that indane derivatives are potent and dual-selective thyromimetics expected to avoid hypothyroidism in some tissues as well as heart toxicity. KTA-439 (29), a representative indane derivative, showed the same high human TRβ selectivity in a binding assay as 3 and higher liver selectivity than 3 in a cholesterol-fed rat model.

MeSH terms

  • Animals
  • Arginine / chemistry
  • Cholesterol / administration & dosage
  • Cholesterol / metabolism
  • Disease Models, Animal
  • Drug Design
  • Drug Evaluation, Preclinical
  • Dyslipidemias / drug therapy
  • Dyslipidemias / metabolism*
  • Humans
  • Indans / chemistry*
  • Ligands
  • Liver / drug effects
  • Liver / metabolism*
  • Male
  • Malonates / chemical synthesis
  • Malonates / chemistry
  • Models, Molecular
  • Molecular Mimicry*
  • Molecular Structure
  • Rats
  • Rats, Wistar
  • Small Molecule Libraries
  • Structure-Activity Relationship
  • Thyroid Hormone Receptors beta / agonists*
  • Thyroid Hormone Receptors beta / metabolism

Substances

  • Indans
  • Ligands
  • Malonates
  • Small Molecule Libraries
  • Thyroid Hormone Receptors beta
  • malonamic acid
  • Arginine
  • Cholesterol