Design and evaluation of fragment-like estrogen receptor tetrahydroisoquinoline ligands from a scaffold-detection approach

J Med Chem. 2011 Apr 14;54(7):2005-11. doi: 10.1021/jm1011116. Epub 2011 Mar 7.

Abstract

A library of small tetrahydroisoquinoline ligands, previously identified via structure- and chemistry-based hierarchical organization of library scaffolds in tree-like arrangements, has been generated as novel estrogen receptor agonistic fragments via traditional medicinal chemistry exploration. The approach described has allowed for the rapid evaluation of a structure-activity relationship of the ligands concerning estrogen receptor affinity and estrogen receptor β subtype selectivity. The structural biological insights obtained from the fragments aid the understanding of larger analogues and constitute attractive starting points for further optimization.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Design*
  • Estrogen Receptor alpha / agonists
  • Estrogen Receptor alpha / antagonists & inhibitors
  • Estrogen Receptor alpha / chemistry
  • Estrogen Receptor alpha / metabolism*
  • Estrogen Receptor beta / agonists
  • Estrogen Receptor beta / antagonists & inhibitors
  • Estrogen Receptor beta / chemistry
  • Estrogen Receptor beta / metabolism*
  • Ligands
  • Models, Molecular
  • Protein Structure, Tertiary
  • Small Molecule Libraries / chemistry
  • Small Molecule Libraries / metabolism
  • Small Molecule Libraries / pharmacology
  • Substrate Specificity
  • Tetrahydroisoquinolines / chemistry*
  • Tetrahydroisoquinolines / metabolism*
  • Tetrahydroisoquinolines / pharmacology

Substances

  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Ligands
  • Small Molecule Libraries
  • Tetrahydroisoquinolines

Associated data

  • PDB/3OMO
  • PDB/3OMP
  • PDB/3OMQ