Discovery of a novel series of 6-azauracil-based thyroid hormone receptor ligands: potent, TR beta subtype-selective thyromimetics

Bioorg Med Chem Lett. 2003 Feb 10;13(3):379-82. doi: 10.1016/s0960-894x(02)00947-2.

Abstract

In this communication, we wish to describe the discovery of a novel series of 6-azauracil-based thyromimetics that possess up to 100-fold selectivities for binding and functional activation of the beta(1)-isoform of the thyroid receptor family. Structure-activity relationship studies on the 3,5- and 3'-positions provided compounds with enhanced TR beta affinity and selectivity. Key binding interactions between the 6-azauracil moiety and the receptor have been determined through of X-ray crystallographic analysis.

MeSH terms

  • Crystallography, X-Ray
  • Drug Design
  • Humans
  • Indicators and Reagents
  • Ligands
  • Models, Molecular
  • Molecular Mimicry
  • Protein Binding
  • Protein Conformation
  • Receptors, Thyroid Hormone / drug effects*
  • Structure-Activity Relationship
  • Thyroid Hormones / pharmacology*
  • Uracil / analogs & derivatives*
  • Uracil / chemistry*
  • Uracil / pharmacology

Substances

  • Indicators and Reagents
  • Ligands
  • Receptors, Thyroid Hormone
  • Thyroid Hormones
  • Uracil
  • azauracil