Hartmann, Rolf W. and Buchborn, Helga and Kranzfelder, Gerhard and Schönenberger, Helmut and Bogden, Arthur E. (1981) Potential antiestrogens. Synthesis and evaluation of mammary tumor inhibiting activity of 1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes. Journal of medicinal chemistry 24 (10), pp. 1192-1197.
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The syntheses of the meso-1,2-dialkyl-1,2-bis(3'-hydroxyphenyl)ethanes [alkyl substituent: CH3 (I) [78682-42-5], C2H5 (II) [71953-72-5], C3H7 (III) [78682-43-6], C4H9 (IV) [78682-44-7], i-C4H9 (V) [78682-45-8], and C5H11 (VI) [78682-46-9]] and of d,l-3,4-bis(3'-hydroxyphenyl)hexane [71953-71-4] are described. In vitro these compds. inhibited the 3H-labeled estradiol [50-28-2] receptor interaction competitively, exhibiting Ka values of 0.20 * 109-0.11 * 106 M-1. In vivo the meso compds. reduced the estrone [53-16-7]-stimulated mouse uterine growth; the most effective compds. were II, III and IV (48, 50, and 45% inhibition, resp.). Compds., II-V showed weak estrogenic activity in the mouse uterine wt. test and in the vaginal cornification test. Compds. I, II, and III exhibited a dose-dependent growth inhibition on the MCF-7 human breast tumor cell line (10-9-10-6 M). These compds. also showed a marked dose-dependent inhibition on the DMBA-induced, hormone-dependent mammary carcinoma of the Sprague-Dawley rat corresponding to their assocn. consts.
|Additional information (public):||CAN 95:126403 2-3 Hormone Pharmacology 591-31-1 Role: RCT (Reactant), RACT (Reactant or reagent) (alkylation of); 71953-71-4P; 71953-72-5P; 78682-42-5P; 78682-43-6P; 78682-44-7P; 78682-45-8P; 78682-46-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and antiestrogenic and neoplasm-inhibiting activity of); 1678-03-1P; 23308-82-9P; 52956-27-1P; 60441-55-6P; 68266-37-5P; 78682-47-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and chlorination of); 68266-39-7P; 71953-69-0P; 78682-40-3P; 78682-41-4P; 78682-49-2P; 78682-50-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and ether cleavage of); 1742-00-3P; 58114-05-9P; 68266-31-9P; 68266-35-3P; 68266-38-6P; 78682-48-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reductive coupling of); 50-28-2 Role: BIOL (Biological study) (receptor binding of, dialkylbis(hydroxyphenyl)ethanes inhibition of); 53-16-7 Role: BIOL (Biological study) (uterus growth stimulation by, dialkylbis(hydroxyphenyl)ethanes inhibition of)|
|Institutions:||Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger|
|Keywords:||Neoplasm inhibitors (dialkylbis(hydroxyphenyl)ethanes as) Receptors Role: BIOL (Biological study) (estradiol binding by, dialkylbis(hydroxyphenyl)ethanes inhibition of) Estrogens Role: BSU (Biological study, unclassified), BIOL (Biological study) (inhibitors, dialkylbis(hydroxyphenyl)ethanes as) Molecular structure-biological activity relationship (antiestrogenic, of dialkylbis(hydroxyphenyl)ethanes) Mammary gland (neoplasm, dialkylbis(hydroxyphenyl)ethanes inhibition of) Molecular structure-biological activity relationship (neoplasm-inhibiting, of dialkylbis(hydroxyphenyl)ethanes) alkylbishydroxyphenylethane prepn antiestrogen phenylethane dialkylbishydroxy antiestrogen antitumor estrogen inhibitor dialkylbishydroxyphenylethane neoplasm inhibitor dialkylbishydroxyphenylethane|
|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 09:34|
|Last Modified:||12 Nov 2010 09:34|