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

Abstract

E-3,4-bis(3',4'-diacetoxyphenyl)hex-3-ene (I) [84675-77-4], E-4(4'-acetoxyphenyl)-3(3',4'-diacetoxyphenyl)hex-3-ene (II) [84675-78-5], and E-4(3'-acetoxyphenyl)-3(3',4'-diacetoxyphenyl)hex-3-ene (III) [84675-79-6] were synthesized by known methods and were tested for biol. effects with respect to their estradiol receptor affinity, uterotropic and antiuterotropic properties, and antitumor activity. All 3 compds. inhibited the interaction of 3H-labeled estradiol [50-28-2] with its receptor. The relative binding affinity values increased in the order; I (1.0) < III (7.6) < II (21.7). In the immature mouse uterine wt. bioassay, the uterotropic activity of the 3 compds. was weak. I and III, but not II, exhibited significant antiuterotropic properties. All 3 compds. inhibited the growth of a postmenopausal hormone-dependent human mammary carcinoma serially implanted in nude mice.