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| Item type: | Article | ||||
|---|---|---|---|---|---|
| Journal or Publication Title: | Journal of medicinal chemistry | ||||
| Publisher: | American Chemical Society | ||||
| Volume: | 27 | ||||
| Number of Issue or Book Chapter: | 7 | ||||
| Page Range: | pp. 819-824 | ||||
| Date: | 1984 | ||||
| Additional Information (public): | CAN 101:17541 2-2 Mammalian Hormones 456-49-5 Role: RCT (Reactant), RACT (Reactant or reagent) (Friedel-Crafts acylation of); 586-37-8; 591-31-1; 705-15-7; 77344-69-5 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 arom. carbonyl compds.); 56724-09-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and Grignard reaction with Me iodide); 2962-14-3P; 5776-76-1P; 65026-51-9P; 65026-54-2P; 74457-89-9P; 74457-90-2P; 74457-91-3P; 78682-42-5P; 78682-49-2P; 89691-22-5P; 89691-23-6P; 89691-24-7P; 89691-25-8P; 89691-26-9P; 89691-27-0P; 89691-28-1P; 89691-29-2P; 89691-30-5P; 89691-31-6P; 89691-32-7P; 89691-33-8P; 89691-34-9P; 89691-35-0P; 89691-36-1P; 89691-37-2P; 89691-38-3P; 89691-39-4P; 89691-40-7P; 89691-41-8P; 89691-43-0P; 89691-44-1P; 89691-45-2P; 89691-46-3P; 89691-47-4P; 89691-48-5P; 89691-49-6P; 89691-50-9P; 89691-51-0P; 89691-52-1P; 89691-53-2P; 89691-54-3P; 89691-55-4P; 89691-56-5P; 89709-53-5P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and antiestrogenic and estrogenic activity of); 73502-04-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn. of); 829-19-6P; 3319-15-1P; 23308-82-9P; 41038-40-8P; 74457-86-6P; 74457-87-7P; 89691-59-8P; 89691-60-1P; 89691-61-2P; 89691-62-3P; 89691-65-6P; 89691-66-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reductive coupling of); 100-06-1; 552-41-0; 3168-59-0; 24826-74-2; 41068-29-5; 41068-36-4; 89691-67-8 Role: RCT (Reactant), RACT (Reactant or reagent) (redn. of) | ||||
| Institutions: | Chemistry and Pharmacy > Institute of Pharmacy > Alumni or Retired Professors > Prof. Schönenberger | ||||
| Projects: | SFB 234 | ||||
| Identification Number: |
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| Keywords: | Estrogens Role: BIOL (Biological study) (and inhibitors, butestrols and metabutestrols as) Neoplasm inhibitors (bis(hydroxymethylphenyl)butane as, of mammary gland) Receptors Role: BIOL (Biological study) (for estrogen, butestrols and metabutestrols binding by) Molecular structure-biological activity relationship (antiestrogenic, of butestrols and metabutestrols) Molecular structure-biological activity relationship (estrogen receptor-binding, of butestrols and metabutestrols) Mammary gland (neoplasm, bis(hydroxymethylphenyl)butane inhibition of) antiestrogen butestrol metabutestrol prepn estrogen receptor binding butestrol metabutestrol antitumor butanebis hydroxymethylphenyl structure activity butestrol metabutestrol antiestrogen | ||||
| 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: | 17647 |
Abstract
The title butestrols and metabutestrols I (R = H, Br, Cl, F, OH, Me, MeO, Et; R1 = 4- or 5- -OH and -MeO) prepd. by reductive coupling of the appropriate 1-phenylethanols with TiCl3/LiAlH4, and cleavage of the obtained meso-methoxy derivs. were evaluated for binding affinity to calf uterine estrogen receptor, estrogenicity, and antiestrogenicity. All compds. but one showed high relative binding ...
Abstract
The title butestrols and metabutestrols I (R = H, Br, Cl, F, OH, Me, MeO, Et; R1 = 4- or 5- -OH and -MeO) prepd. by reductive coupling of the appropriate 1-phenylethanols with TiCl3/LiAlH4, and cleavage of the obtained meso-methoxy derivs. were evaluated for binding affinity to calf uterine estrogen receptor, estrogenicity, and antiestrogenicity. All compds. but one showed high relative binding affinity values 1-29% of that of estradiol. meso-2,3-Bis(5-hydroxy-2-methylphenyl)butane (I; R = Me, R1 = 5-OH) [89691-38-3] showed high estradiol receptor affinity, antiestrogenic and weak estrogenic properties, and inhibition of tumor growth on induced, hormone-dependent mammary carcinoma. Structure-activity relations are discussed.
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