title: Synthesis and evaluation of catechol analogs of diethylstilbestrol on a hormone-dependent human mammary carcinoma implanted in nude mice.
abstract: 3,4-Bis(3',4'-diacetoxyphenyl)hex-3-ene (5a), 4(4'-acetoxyphenyl)-3(3',4'-diacetoxyphenyl)hex-3-ene (5b), and 4(3'-acetoxyphenyl)-3(3',4'-diacetoxyphenyl)hex-3-ene (5c) were synthesized according to the method of Dodds et al. (1939). All compounds inhibited the interaction of 3H-estradiol with its receptor. The relative binding affinity (RBA) values increased in the order: 5a (1.0) less than 5c (7.6) less than 5b (21.7). In the immature mouse uterine weight bioassay, the uterotrophic activity of 5a-c was only weak. 5a and 5c, but not 5b, exhibited significant antiuterotrophic properties. All compounds significantly inhibited the growth of a postmenopausal hormone-dependent human mammary carcinoma serially implanted in nude mice.
mesh_terms: D000818:Animals; D001943:Breast Neoplasms / Q000378:metabolism*; D004054:Diethylstilbestrol / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000378:metabolism*; D002393:Estrogens, Catechol / Q000138:chemical synthesis / Q000378:metabolism*; D005260:Female; D006801:Humans; D051379:Mice; D008819:Mice, Nude; D009368:Neoplasm Transplantation; D009374:Neoplasms, Experimental; D009376:Neoplasms, Hormone-Dependent / Q000378:metabolism*; D009929:Organ Size / Q000187:drug effects; D011959:Receptors, Estradiol; D011960:Receptors, Estrogen / Q000378:metabolism; D014599:Uterus / Q000187:drug effects
chemical_list: D002393:Estrogens, Catechol; D011959:Receptors, Estradiol; D011960:Receptors, Estrogen; D004054:Diethylstilbestrol