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

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. (c) 2010. Published by Elsevier Inc. All rights reserved.