title: A novel fluorinated derivative of diethylstilbestrol.
abstract: The synthesis of the 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 microgram/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.
mesh_terms: D000818:Animals; D001667:Binding, Competitive; D001681:Biological Assay; D004054:Diethylstilbestrol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000494:pharmacology; D005260:Female; D008722:Methods; D051379:Mice; D011960:Receptors, Estrogen / Q000378:metabolism; D014599:Uterus / Q000187:drug effects / Q000378:metabolism
chemical_list: D011960:Receptors, Estrogen; D004054:Diethylstilbestrol