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Bioorg Med Chem Lett. 2012 Jun 1;22(11):3713-7. doi: 10.1016/j.bmcl.2012.04.022. Epub 2012 Apr 11.

BC-spiro-estradiols. Synthesis and estrogen receptor binding affinity of four new estradiol isomers.

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  • 1Department of Chemistry, University of Ottawa, Ottawa, Canada.


The synthesis of four new isomers of estradiol in which the ring A to ring C planes are perpendicular to each other as a result of a spiro BC ring junction is described. Heterocyclic analogs and carbocyclic homologs of these compounds are also reported. Estrogen receptor binding studies show that the spiro compounds with the natural stereochemistry at C9 bind almost as strongly as estradiol but with greater β to α selectivity. These studies show that the estrogen receptors can readily accommodate isomers of estrogen with substantially different fixed shapes than the native ligand.

Copyright © 2012. Published by Elsevier Ltd.

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