Schneider, M. R. and Schönenberger, Helmut and Michel, R. T. and Fortmeyer, H. P. (1982) Synthesis and evaluation of catechol analogs of diethylstilbestrol on a hormone-dependent human mammary carcinoma implanted in nude mice. Journal of cancer research and clinical oncology 104 (3), pp. 219-227.
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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.
|Additional information (public):||CAN 98:119855 2-4 Mammalian Hormones 91-16-7 Role: RCT (Reactant), RACT (Reactant or reagent) (acylation of); 4927-54-2P; 4927-55-3P; 84675-71-8P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and alkylation of); 56-53-1DP; 84675-77-4P; 84675-78-5P; 84675-79-6P Role: BAC (Biological activity or effector, except adverse), BSU (Biological study, unclassified), SPN (Synthetic preparation), BIOL (Biological study), PREP (Preparation) (prepn. and biol. activity of); 75513-68-7P; 84675-75-2P; 84675-76-3P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and ether cleavage and acetylation of); 84675-72-9P; 84675-73-0P; 84675-74-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reaction with Et magnesium bromide and dehydration of); 50-28-2 Role: BIOL (Biological study) (receptor binding of, DES catechol analogs interaction in)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Neoplasm inhibitors (DES catechol analogs) Uterus (DES catechol analogs effect on growth of) Receptors Role: BIOL (Biological study) (estradiol binding by, DES catechol analog interaction in) Carcinoma (of mammary gland, DES catechol analogs inhibition of) Mammary gland (neoplasm, carcinoma, DES catechol analogs inhibition of) DES catechol analog prepn estrogen carcinoma mammary inhibition DES analog uterus growth DES catechol analog|
|Subjects:||500 Science > 540 Chemistry & allied sciences|
|Refereed:||Yes, this version has been refereed|
|Created at the University of Regensburg:||Yes|
|Deposited On:||12 Nov 2010 09:21|
|Last Modified:||12 Nov 2010 09:21|