Thyroid receptor ligands. Part 2: Thyromimetics with improved selectivity for the thyroid hormone receptor beta

Bioorg Med Chem Lett. 2004 Jul 5;14(13):3549-53. doi: 10.1016/j.bmcl.2004.04.032.

Abstract

A set of thyromimetics having improved selectivity for TR-beta1 were prepared by replacing the 3'-isopropyl group of 2 and 3 with substituents having increased steric bulk. From this limited SAR study, the most potent and selective compounds identified were derived from 2 and contained a 3'-phenyl moiety bearing small hydrophobic groups meta to the biphenyl link. X-ray crystal data of 15c complexed with TR-beta1 LBD shows methionine 442 to be displaced by the bulky R3' phenyl ethyl amide side chain. Movement of this amino acid side chain provides an expanded pocket for the bulky side chain while the ligand-receptor complex retains full agonist activity.

MeSH terms

  • 2-Propanol / chemistry
  • Amino Acids / chemistry
  • Binding Sites
  • Cell Line
  • Crystallography, X-Ray
  • Drug Design
  • Inhibitory Concentration 50
  • Ligands
  • Structure-Activity Relationship
  • Thyroid Hormone Receptors beta / drug effects
  • Thyroid Hormone Receptors beta / metabolism*
  • Thyroid Hormones / chemistry*
  • Thyroid Hormones / metabolism
  • Thyroid Hormones / pharmacology
  • Triiodothyronine / chemistry*
  • Triiodothyronine / metabolism
  • Triiodothyronine / pharmacology

Substances

  • Amino Acids
  • Ligands
  • Thyroid Hormone Receptors beta
  • Thyroid Hormones
  • Triiodothyronine
  • 2-Propanol

Associated data

  • PDB/1R6G