Estrogen receptor ligands. Part 4: The SAR of the syn-dihydrobenzoxathiin SERAMs

Bioorg Med Chem Lett. 2004 Jun 7;14(11):2741-5. doi: 10.1016/j.bmcl.2004.03.074.

Abstract

A series of estrogen receptor ligands based on a dihydrobenzoxathiin scaffold is described and evaluated for estrogen/anti-estrogen activity in both in vitro and in vivo models. The most active analogue, 22, was found to be 40-fold ERalpha selective in a competitive binding assay, and 22 demonstrated very potent in vivo antagonism of estradiol driven proliferation in an immature rat uterine weight gain assay.

MeSH terms

  • Animals
  • Binding, Competitive
  • Cell Line, Tumor
  • Cell Proliferation / drug effects
  • Estrogen Receptor alpha / chemistry*
  • Estrogen Receptor beta / chemistry
  • Female
  • Heterocyclic Compounds, 4 or More Rings / chemical synthesis
  • Heterocyclic Compounds, 4 or More Rings / pharmacokinetics
  • Heterocyclic Compounds, 4 or More Rings / pharmacology
  • Humans
  • Ligands
  • Organ Size
  • Oxathiins / chemical synthesis
  • Oxathiins / pharmacokinetics
  • Oxathiins / pharmacology*
  • Protein Binding
  • Rats
  • Rats, Sprague-Dawley
  • Selective Estrogen Receptor Modulators / chemical synthesis*
  • Selective Estrogen Receptor Modulators / pharmacokinetics
  • Selective Estrogen Receptor Modulators / pharmacology
  • Structure-Activity Relationship
  • Uterus / drug effects

Substances

  • Estrogen Receptor alpha
  • Estrogen Receptor beta
  • Heterocyclic Compounds, 4 or More Rings
  • Ligands
  • Oxathiins
  • Selective Estrogen Receptor Modulators
  • syn-dihydrobenzoxathiin