Conversion of the phytoestrogen coumestrol into a selective estrogen receptor modulator (SERM) by attachment of an amine-containing sidechain

The naturally occurring estrogen mimetic coumestrol has been shown to stimulate proliferation of MCF-7 mammary tumor cells and to cause uterotrophic effects in ovariectomized (OVX) rats. Attachment of a basic amine-containing sidechain to C-6 of coumestrol converts this estrogen agonist into an antagonist in breast and uterine tissue, while maintaining its estrogen-like activity as a hypocholesterolemic agent.