Synthesis and evaluation of catechol analogs of diethylstilbestrol on a hormone-dependent human mammary carcinoma implanted in nude mice.

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.