Aza analogues of equol: novel ligands for estrogen receptor beta

Bioorg Med Chem. 2007 Sep 1;15(17):5828-36. doi: 10.1016/j.bmc.2007.05.071. Epub 2007 Jun 6.

Abstract

3-Aryl-tetrahydroquinolines, aza analogues of equol, are synthesized and evaluated for their binding properties to the estrogen receptors ERalpha and ERbeta. Several of these compounds exhibited binding selectivity for ER similar to that of genistein. Compounds 8c and 8d were found to have dual actions: antagonists for ERalpha and agonists for ERbeta in a yeast two-hybrid assay. These compounds have no estrogenic effects on the uterus and bone in vivo.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Animals
  • Aza Compounds / chemical synthesis*
  • Aza Compounds / chemistry
  • Aza Compounds / pharmacology*
  • Bone Density
  • Equol
  • Estrogen Receptor alpha / metabolism
  • Estrogen Receptor beta / metabolism*
  • Female
  • Humans
  • Isoflavones / chemical synthesis
  • Isoflavones / chemistry*
  • Isoflavones / pharmacology*
  • Ligands
  • Molecular Structure
  • Rats
  • Structure-Activity Relationship
  • Uterus / drug effects

Substances

  • 4',7-dihydroxy-3,4-dihydroisoflavone
  • Aza Compounds
  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Isoflavones
  • Ligands
  • Equol