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Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols

Hartmann, Rolf W. and Heindl, Aledander and Schönenberger, Helmut (1984) Ring-substituted 1,2-dialkylated 1,2-bis(hydroxyphenyl)ethanes. 2. Synthesis and estrogen receptor binding affinity of 4,4'-, 5,5'-, and 6,6'-disubstituted metahexestrols. Journal of medicinal chemistry 27 (5), pp. 577-585.

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Abstract

Sym. 4,4'-, 5,5'-, and 6,6'-disubstituted derivs. of the mammary tumor-inhibiting antiestrogen metahexestrol (meso-I, R = H) (II) were prepd. Reductive coupling of EtCOC6H4R with TiCl4/Zn followed by hydrogenation, or reductive coupling of EtCH(OH)C6H4R with TiCl3/LiAlH4, and sepn. of the diastereomers, or substitution reaction of II gave meso-I (R = Me, MeOCH2, EtOCH2, HOCH2, halo, NO2, OH, amino, etc.). In the calf uterine estrogen receptor binding assay meso-I had binding affinities 0.01-15% that of estradiol. Only meso-I (R = 6-Me) had a binding affinity > II. In the mouse uterine wt. test meso-I (R = 4-Me, 6-Cl) had strongly enhanced estrogenicity compared to II. meso-I (R = 4-F, 4-Me, 4-H2N, 6-Me) and II were antiestrogenic, giving 24-60% inhibition of estrone-stimulated uterine growth.

Item Type:

Article

Additional information (public):

CAN 100:156305 25-7 Benzene, Its Derivatives, and Condensed Benzenoid Compounds 71953-69-0 Role: RCT (Reactant), RACT (Reactant or reagent) (Friedel-Crafts acetylation of); 33719-74-3 Role: RCT (Reactant), RACT (Reactant or reagent) (Grignard carboxylation of); 82846-18-2 Role: RCT (Reactant), RACT (Reactant or reagent) (acid chloride prepn. from); 102-50-1 Role: RCT (Reactant), RACT (Reactant or reagent) (diazotization and fluorination of); 71953-72-5 Role: RCT (Reactant), RACT (Reactant or reagent) (estrogenic and antiestrogenic activity of); 367-83-9P; 578-39-2P; 82846-19-3P; 89106-53-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and Grignard ethylation of); 52238-48-9P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and alkali fusion of); 89106-15-0P; 89106-19-4P; 89106-20-7P; 89106-21-8P; 89106-23-0P; 89106-25-2P; 89106-26-3P; 89106-27-4P; 89106-29-6P; 89106-30-9P; 89106-32-1P; 89106-34-3P; 89106-37-6P; 89106-40-1P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogen receptor binding activity of); 89106-12-7P; 89106-22-9P; 89106-28-5P; 89106-43-4P; 89106-47-8P; 89106-50-3P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and estrogenic and antiestrogenic activity of); 71953-69-0P; 89106-13-8P; 89106-16-1P; 89106-33-2P; 89106-35-4P; 89106-38-7P; 89106-41-2P; 89106-44-5P; 89106-48-9P; 89106-51-4P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. and ether cleavage of); 89106-31-0P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrazine redn. of); 76473-05-7P; 89106-14-9P; 89106-17-2P; 89106-36-5P; 89106-45-6P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and hydrogenation of); 2338-54-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn. of); 29578-81-2P; 37951-49-8P; 41497-31-8P; 82846-20-6P; 89106-18-3P; 89106-39-8P; 89106-42-3P; 89106-46-7P; 89106-49-0P; 89106-52-5P; 89121-16-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and reductive self-coupling of); 82477-67-6P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, and acid chloride prepn. from); 89106-54-7P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of, and sodium salt prepn. from); 89106-24-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn., sapon., and alkylation of); 118-90-1 Role: RCT (Reactant), RACT (Reactant or reagent) (sulfonation of)

Institutions:

Chemistry and Pharmacy > Institute of Pharmacy > Retired Professors > Prof. Schönenberger

Projects:

SFB 234

Identification Number:

Value	Type
1984:156305	Other

Keywords:

Estrogens Role: RCT (Reactant), RACT (Reactant or reagent) (and inhibitors, metahexestrol derivs.) Molecular structure-biological activity relationship (antiestrogenic, of metahexestrol derivs.) Molecular structure-biological activity relationship (estrogenic, of metahexestrol derivs.) Coupling reaction (reductive, of phenylpropanols and propiophenones, mesohexestrol derivs. by) metahexestrol deriv prepn estrogen antiestrogen hexanediol diphenyl deriv

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 10:02