Studies in antifertility agents. 50. Stereoselective binding of d- and l-centchromans to estrogen receptors and their antifertility activity

Centchroman [dl-3,4-trans-2,2-dimethyl-3-phenyl-4-[p-(beta-pyrrolidinoethoxy)phenyl] - 7-methoxychroman hydrochloride], an antifertility agent under clinical evaluation, has been resolved into its optical enantiomers. The cytosol estrogen receptor binding affinity and estrogenic, antiestrogenic and antiimplantation activities of the two enantiomers have been determined. The enantiomers display a 7-fold difference in receptor affinity, and a corresponding difference in stimulation of the uterine growth and antiimplantation activity was observed in rats.