Structure-activity study of estrogenic agonists bearing dicarba-closo-dodecaborane. Effect of geometry and separation distance of hydroxyl groups at the ends of molecules

Bioorg Med Chem Lett. 1999 Dec 6;9(23):3313-8. doi: 10.1016/s0960-894x(99)00596-x.

Abstract

Dicarba-closo-dodecaboranes (carboranes), which have spherical geometry and hydrophobicity, are applicable as a hydrophobic pharmacophore of biologically active molecules. We have investigated structure-activity relations based on the structure of the potent estrogenic agonist, 1-hydroxymethyl-12-(4-hydroxyphenyl)-1,12-dicarba-closo-d odecaborane, which we have previously reported. The geometry and separation distance of the phenolic and alcoholic hydroxyl groups play a critical role in the appearance of biological activity.

MeSH terms

  • Animals
  • Boron Compounds / chemistry*
  • Boron Compounds / metabolism
  • Boron Compounds / pharmacology*
  • COS Cells
  • Estrogens / agonists*
  • Hydroxyl Radical
  • Molecular Structure
  • Rats
  • Receptors, Estrogen / agonists
  • Receptors, Estrogen / metabolism
  • Structure-Activity Relationship

Substances

  • 1-hydroxymethyl-12-(4-hydroxyphenyl)-1,12-dicarbadodecaborane
  • Boron Compounds
  • Estrogens
  • Receptors, Estrogen
  • Hydroxyl Radical