NOVEL FLUORINATED DERIVATIVE OF DIETHYLSTILBESTROL

The synthesis of a diethylstilbestrol (DES) derivative with fluorine atoms present in the positions ortho to the hydroxyl in each ring is described, In vitro studies in a system containing horse radish peroxidase /H2O2 demonstrate extensive oxidation of tetrafluorodiethylstilbestrol to the corresponding dienestrol derivative. Tetrafluorodiethylstilbestrol and DES had comparable In vivo uterotropic activities at a dose of 100 μg/ kg. Competitive binding experiments demonstrated 20-25 fold reduced interaction with the mouse uterine estrogen receptor. This compound may be useful as an experimental estrogen in distinguishing between the biological and toxic effects of DES. © 1979.