Benzopyrans as selective estrogen receptor beta agonists (SERBAs). Part 2: structure-activity relationship studies on the benzopyran scaffold

Bioorg Med Chem Lett. 2007 Jul 1;17(13):3570-4. doi: 10.1016/j.bmcl.2007.04.051. Epub 2007 Apr 25.

Abstract

Benzopyrans are selective estrogen receptor (ER) beta agonists (SERBAs), which bind the ER subtypes alpha and beta in opposite orientations. Here we describe structure-activity relationship studies that led to the discovery of bezopyran 5b. X-ray crystal structures of 5b and a non-selective analog 5c in ERalpha help explain the observed selectivity of the benzopyran platform.

MeSH terms

  • Benzopyrans / pharmacology*
  • Chemistry, Pharmaceutical / methods*
  • Crystallography, X-Ray
  • Drug Design
  • Estrogen Receptor alpha / chemistry
  • Estrogen Receptor beta / agonists*
  • Estrogen Receptor beta / chemistry
  • Female
  • Humans
  • Ligands
  • Male
  • Models, Chemical
  • Models, Molecular
  • Selective Estrogen Receptor Modulators / pharmacology*
  • Structure-Activity Relationship
  • Transcription Factors / metabolism

Substances

  • Benzopyrans
  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Ligands
  • Selective Estrogen Receptor Modulators
  • Transcription Factors