Thyroid receptor ligands. Part 5: novel bicyclic agonist ligands selective for the thyroid hormone receptor beta

Bioorg Med Chem Lett. 2006 Mar 1;16(5):1240-4. doi: 10.1016/j.bmcl.2005.11.077. Epub 2005 Dec 9.

Abstract

Based on the examination of the crystal structure of rat TRbeta complexed with 3,5,3'-triiodo-l-thyronine (2) a novel TRbeta-selective indole derivative 6b was prepared and tested in vitro. This compound was found to be 14 times selective for TRbeta over TRalpha in binding and its beta-selectivity could be rationalized through the comparison of the X-ray crystallographic structures of 6b complexed with TRalpha and TRbeta.

MeSH terms

  • Animals
  • Crystallography, X-Ray
  • Cyclization
  • Humans
  • Indoles / chemistry*
  • Indoles / metabolism
  • Indoles / pharmacology*
  • Inhibitory Concentration 50
  • Ligands
  • Molecular Structure
  • Rats
  • Substrate Specificity
  • Thyroid Hormone Receptors beta / agonists*
  • Thyroid Hormone Receptors beta / chemistry
  • Thyroid Hormone Receptors beta / metabolism*
  • Thyroxine / chemical synthesis
  • Thyroxine / chemistry

Substances

  • Indoles
  • Ligands
  • Thyroid Hormone Receptors beta
  • Thyroxine