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| Item type: | Article | ||||
|---|---|---|---|---|---|
| Journal or Publication Title: | Journal of medicinal chemistry | ||||
| Publisher: | American Chemical Society | ||||
| Volume: | 28 | ||||
| Number of Issue or Book Chapter: | 9 | ||||
| Page Range: | pp. 1295-1301 | ||||
| Date: | 1985 | ||||
| Additional Information (public): | CAN 103:81258 1-3 Pharmacology 829-20-9; 2150-40-5; 24826-74-2; 41068-36-4; 54810-63-8; 73502-03-1; 74457-86-6; 96826-41-4; 96826-42-5 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with Me iodide); 74-88-4 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard reaction of, with methoxyacetophenones); 7428-99-1P; 55311-42-7P; 72667-90-4P; 91968-30-8P; 96826-25-4P; 96826-26-5P; 96826-27-6P; 96826-28-7P; 96826-29-8P; 96826-30-1P; 96826-31-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and autocoupling of); 96826-23-2P; 96826-24-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogen receptor binding affinity of); 74385-27-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogen receptor-binding affinity and estrogenic activity of); 96826-17-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic and antiestrogenic and mammary tumor-inhibiting activities of); 96826-21-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic receptor binding affinity binding of); 96826-19-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic receptor binding affinity of); 96826-18-5P; 96826-20-9P; 96844-92-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic-antiestrogenic activity of); 96826-22-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic-antiestrogenic and mammary tumor-inhibiting activities of); 32445-98-0P; 74385-22-1P; 96826-32-3P; 96826-33-4P; 96826-34-5P; 96826-35-6P; 96826-36-7P; 96826-37-8P; 96826-38-9P; 96826-39-0P; 96826-40-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and ether cleavage of); 74385-30-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and relative binding affinity and estrogenic-antiestrogenic activity of) | ||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger | ||||
| Identification Number: |
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| Keywords: | Receptors Role: BIOL (Biological study) (for estrogens, tetramethylbis(hydroxyphenyl)ethanes binding by) Estrogens Role: BSU (Biological study, unclassified), BIOL (Biological study) (inhibitors, tetramethylbis(hydroxyphenyl)ethanes, receptor binding in relation to) Neoplasm inhibitors (tetramethylbis(hydroxyphenyl)ethanes) Molecular structure-biological activity relationship (antiestrogenic, of tetramethylbis(hydroxyphenyl)ethanes) Mammary gland (neoplasm, inhibition of, by tetramethylbis(hydroxyphenyl)ethanes) Molecular structure-biological activity relationship (neoplasm-inhibiting, of tetramethylbis(hydroxyphenyl)ethanes) methylbishydroxyphenylethane prepn antiestrogen antitumor butestrol deriv prepn antiestrogen antitumor metabutestrol deriv prepn antiestrogen antitumor antiestrogen butestrol metabutestrol deriv mammary antitumor butestrol metabutestrol deriv structure activity methylbishydroxyphenylethane | ||||
| Dewey Decimal Classification: | 500 Science > 540 Chemistry & allied sciences | ||||
| Status: | Published | ||||
| Refereed: | Yes, this version has been refereed | ||||
| Created at the University of Regensburg: | Yes | ||||
| Item ID: | 17652 |
Abstract
The title compds. I (R = R1 = H, Cl, F, Me, MeO, OH) prepd. by coupling the corresponding substituted 2-(methoxyphenyl)-2-propanol using TiCl3/LiAlH4 and subsequent ether cleavage of the products, were evaluated for estrogenic, antiestrogenic, and mammary tumor-inhibiting activities. The relative binding affinity was detd. by displacement of [3H]estradiol after incubation with calf uterine ...
Abstract
The title compds. I (R = R1 = H, Cl, F, Me, MeO, OH) prepd. by coupling the corresponding substituted 2-(methoxyphenyl)-2-propanol using TiCl3/LiAlH4 and subsequent ether cleavage of the products, were evaluated for estrogenic, antiestrogenic, and mammary tumor-inhibiting activities. The relative binding affinity was detd. by displacement of [3H]estradiol after incubation with calf uterine cytosol. Estrogenic and antiestrogenic activities were detd. by stimulation of uterine growth and inhibition of the uterine growth stimulated by estrone. Tumor-inhibiting effect was detd. by using the DMBA-induced, hormone-dependent mammary adenocarcinoma of the SD-rat. Most compds. showed an increase in uterotrophic and a decrease in antiuterotrophic activity compared to the unsubstituted ones. 2,3-Bis(2-fluoro-4-hydroxyphenyl)-2,3-dimethylbutane (I, R = 2-fluoro; R1 = 4-OH) [96826-17-4] showed a strong, dose-dependent antitumor activity exceeding that of the parent 2,3-bis-(4-hydroxyphenyl)-2,3-dimethylbutane (I, R = H; R1 = 4-OH) [74385-27-6]; at 5 mg/kg/day reduced total tumor area by 47% and caused a complete remission in 74% of the tumors. Structure-activity relations are discussed.
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