ERbeta ligands. Part 4: Synthesis and structure-activity relationships of a series of 2-phenylquinoline derivatives

Bioorg Med Chem Lett. 2005 Oct 15;15(20):4520-5. doi: 10.1016/j.bmcl.2005.07.008.

Abstract

A new class of estrogen receptor beta (ERbeta) ligands based on the 2-phenylquinoline scaffold was prepared. Several analogues with C4 substitution displayed high affinity (3-5 nM) and significant selectivity (up to 83-fold) for ERbeta. The best compound, 13b, was profiled as a selective partial agonist for ERbeta at 1 muM in a cell-based transcriptional assay. Uterine weight bioassay of 13b indicated no activation of ERalpha in vivo.

MeSH terms

  • Benzoquinones / chemical synthesis*
  • Benzoquinones / chemistry
  • Benzoquinones / metabolism
  • Benzoquinones / pharmacology*
  • Estrogen Receptor beta / metabolism*
  • Models, Molecular
  • Radioligand Assay
  • Structure-Activity Relationship

Substances

  • Benzoquinones
  • Estrogen Receptor beta
  • phenylbenzoquinone