Synthesis of 17 alpha-substituted ethynylestradiols: potential ligands for drug vectors

Steroids. 2010 Jul;75(7):489-98. doi: 10.1016/j.steroids.2010.03.004. Epub 2010 Mar 17.

Abstract

17alpha-substituted ethynylestradiols, derived from estrone, were converted to their corresponding 17 alpha-(bromo- or iodo-propargyl)estrone intermediates. Nucleophilic substitution onto these moieties with malonate diester followed by hydrolysis and complexation with cis-Pt(Me(2)en)I(2) (Me(2)en=N,N-dimethylethylenediamine) gave cis-Pt(Me(2)en)(2-(3-(17beta-estradiol-17 alpha-yl)-prop-2-ynyl)malonato) 7, thus demonstrating that these estrogen-derived compounds can be used to synthesize stable Pt(II) complexes. The 3-(17beta-estradiol-17 alpha-yl)-prop-2-ynyl-1-sulfanylethylthiol 23 was also prepared.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Drug Carriers
  • Ethinyl Estradiol / chemical synthesis*
  • Ethinyl Estradiol / chemistry
  • Ligands
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Models, Chemical*
  • Molecular Structure

Substances

  • Drug Carriers
  • Ligands
  • Ethinyl Estradiol