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Syntheses and evaluation of the potentially estrophilic cytostatics. 2,3-Epoxy-3,4-bis(4'-acetoxyphenyl)-4-hexene and 2,3,4,5-bisepoxy-3,4-bis(4'-acetoxyphenyl)hexane

Schneider, Martin R. ; Schönenberger, Helmut ; Michel, Ralf T. ; Fortmeyer, Hans P.


Acetylating (E,E)-[4-ROC6H4C(:CHMe)]2 [(E,E)-I, R = H] gave (E,E)-I (R = Ac), epoxidn. of which with 3-ClC6H4C(O)OOH gave 66% epoxide II, further epoxidn. of which gave diepoxide III. (E,E)-I (R = Ac), II, and III competitively inhibit the interaction of estradiol-t with its receptor, (E,E)-I (R = Ac) > II > III, and the growth of a human mammary carcinoma transplanted in thymus aplastia mice.

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