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Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 3. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of 2,2'-disubstituted butestrols and 6,6'-disubstituted metabutestrols

Hartmann, Rolf W. and Heindl, Alexander and Schwarz, Walter and Schönenberger, Helmut (1984) Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 3. Synthesis, estrogen receptor binding affinity, and evaluation of antiestrogenic and mammary tumor inhibiting activity of 2,2'-disubstituted butestrols and 6,6'-disubstituted metabutestrols. Journal of medicinal chemistry 27 (7), pp. 819-824.

Full text not available from this repository.

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.

Item Type:

Article

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 > Retired Professors > Prof. Schönenberger

Projects:

SFB 234

Identification Number:

Value	Type
1984:417541	Other

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

Subjects:

500 Science > 540 Chemistry & allied sciences

Status:

Published

Refereed:

Yes, this version has been refereed

Created at the University of Regensburg:

Yes

Owner:

Petra Gürster

Deposited On:

12 Nov 2010 10:01