79578-62-4

Usage

Uses

Used in Pharmaceutical Industry:
4-(2-Bromoethoxy)-4'-hydroxybenzophenone is used as a key intermediate in the preparation of estrogen receptor modulators for the treatment of various hormone-related conditions. Its ability to interact with estrogen receptors makes it a promising candidate for the development of drugs that can help regulate hormonal balance and alleviate symptoms associated with estrogen deficiency or imbalance.

Preparation

Preparation by reaction of 4-hydroxybenzoic acid with b-bromophenetole, in solution of a polyphosphoric acid/85% phosphoric acid/zinc chloride mixture. The solution was heated to 50–60°, phosphorous trichloride was added during 1 h and the mixture heated for 20 h at 70° (74%).

Upstream product

• 557-91-5 1,1-Dibromoethane 
• 737816-47-6 C₂₁H₂₇BrO₃Si 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-41-2 4-bromo-phenol 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 185223-77-2 [4-(2-Bromo-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methanone 
• 589-10-6 phenoxyethyl bromide 
• 99-96-7 4-hydroxy-benzoic acid 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 106-93-4 ethylene dibromide 

Downstream Products

• 147323-02-2 E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene 
• 110025-28-0 (E/Z)-4-[1-[4-[2-(methylamino)ethoxy]phenyl]-2-phenyl-1-buten-1-yl]-phenol 
• 185223-81-8 (4-{(E)-1-[4-(2-Bromo-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenoxy)-acetic acid 
• 141777-00-6 (E,Z)-4-<1-(p-hydroxyphenyl)-2-phenyl-1-butenyl>phenoxyacetic acid 

Relevant academic research and scientific papers

NOVEL COMPOUNDS HAVING ESTROGEN RECEPTOR ALPHA DEGRADATION ACTIVITY AND USES THEREOF

The present disclosure relates to novel compounds having estrogen receptor alpha degradation activity, pharmaceutical compositions containing such compounds, and their use in prevention and treatment of cancer and related diseases and conditions.

PROCESS FOR PREPARING (Z)-ENDOXIFEN OF HIGH PURITY

Disclosed is a process for preparing (Z)-endoxifen, comprising (i) recrystallizing an input crystalline solid comprising a mixture of (Z)-endoxifen (1) and (E)-endoxifen (2) from a first solvent to provide a first crystalline solid and a first mother liqu

Design and synthesis of norendoxifen analogues with dual aromatase inhibitory and estrogen receptor modulatory activities

Both selective estrogen receptor modulators and aromatase inhibitors are widely used for the treatment of breast cancer. Compounds with both aromatase inhibitory and estrogen receptor modulatory activities could have special advantages for treatment of br

7-NITROINDOLINE DERIVATIVES AND THEIR USES

7-nitroindoline compounds are disclosed that comprise a triplet sensitising group such as substituted or unsubstituted benzophenone group and can be used to cage effector species. In particular, the inclusion of a triplet sensitising group linked to the 4 or 5 position of a 7-nitroindoline derivative provides compounds which can be photolysed to release the effector species with unexpectedly enhanced photolysis efficiency. The triplet sensitising group may be linked directly to the 7-nitroindoline or via a spacer group. In some examples, the triplet sensitising group and/or the spacer group can be selected to enhance other properties of the caged compound such as its solubility, spectroscopic properties or stability (e.g. stability of the linkage between the nitroindoline moiety and the triplet sensitiser). This can help to improve the performance of the caged compound, especially in aqueous environments containing dissolved oxygen.

Estrogenic triarylethylene acetic acids: Effect of structural variation on estrogen receptor affinity and estrogenic potency and efficacy in MCF-7 cells

Triarylethylenecarboxylic acids exemplified by (E,Z)-2-{4-[1-(p- hydroxyphenyl)-2-phenyl]-1-butenyl}phenoxyacetic acid (8) are a new class of estrogen receptor (ER) ligands capable of tissue selective estrogen agonist and antagonist effects. We report the syntheses of 8 and of analogues incorporating structural features known or anticipated to facilitate ER affinity in triarylethylenes. These studies revealed that the p- hydroxyphenyl moiety, ethylenic bond, and ether oxygen of 8 were all critical for high ER affinity. Although a 1,1-bisphenolic analogue bearing the p- (oxyacetic acid) moiety on its 2-phenyl ring, 12, had low ER affinity, it exhibited estrogenic potency approaching that of 8 in MCF-7 cells. Unlike 8 which was a partial agonist with weak antagonist potency, 12 was a full agonist. A similar profile of potency/efficacy in MCF-7 cells was seen in 9, an ethylenic bond saturated analogue of 8. Growth-promoting effects of 8, 9, and 12 were fully antagonized by the antiestrogen tamoxifen, suggesting that such effects were mediated solely via ER. Thus, our studies in MCF-7 cells have confirmed the estrogenicity of 8 and have enabled identification of two analogues with favorable estrogenic potency and full estrogen efficacy. On this basis, these three (triarylethylene)acetic acids have been selected for more intensive animal studies of their extrareproductive tract estrogenic effects.

Triarylethylene carboxylic acids with estrogenic activity

Nonsteroidal estrogenic triarylethylene carboxylic acids of the formula STR1 wherein R is (CH 2) m O or (CH 2) n, where m is an integer from 1 to 4 and n is an integer from 0 to 4, X is hydrogen or hydroxyl, Y is methyl, ethyl, chlorine, or bromine, and wherein the RCOOH and X moieties are either meta or para to the phenyl ethylene linkage. Examples of active compounds include 4-hydroxytamoxifen acid, 3-hydroxytamoxifen acid, 4-[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]benzoic acid and 4-[1-(p-hydroxyphenyl)-2-phenyl-1-butenyl]phenylacetic acid. Compositions containing these triarylethylene carboxylic acids can be administered to patients to alleviate medical conditions associated with a deficiency of estrogen, including osteoporosis, premenstrual syndrome, vasomotor symptoms associated with menopause, atrophic vaginitis, Kraurosis vulvae, female hypogonadism, primary ovarian failure, excessive hair growth and prThe U.S. Government has certain rights in this invention by virtue of grants from the National Institutes of Health.