51777-15-2

Usage

Uses

Used in Pharmaceutical Industry:
4-(DiMethylaMinoethoxy)benzophenone is used as a photo-degradation product for Tamoxifen (T006000), which is a medication with multiple applications in the treatment of various conditions. As a SERM, it can be employed for hormone regulation, while its protein kinase C inhibitor and anti-angiogenetic properties make it useful in the treatment of certain cancers by inhibiting cell growth and blood vessel formation.
Used in Research and Development:
In the field of research and development, 4-(DiMethylaMinoethoxy)benzophenone serves as a valuable compound for studying the degradation of Tamoxifen and its potential effects on the drug's efficacy and safety. This knowledge can contribute to the development of improved drug formulations and delivery systems, as well as a better understanding of the drug's mechanism of action.
Used in Quality Control and Analysis:
4-(DiMethylaMinoethoxy)benzophenone can be utilized in the quality control and analysis of Tamoxifen and its formulations. By monitoring the presence and concentration of 4-(DiMethylaMinoethoxy)benzophenone, researchers and pharmaceutical companies can ensure the stability, purity, and overall quality of Tamoxifen products, ultimately contributing to their safety and effectiveness for patients.

InChI:InChI=1/C17H19NO2/c1-18(2)12-13-20-16-10-8-15(9-11-16)17(19)14-6-4-3-5-7-14/h3-11H,12-13H2,1-2H3

Upstream product

• 141-52-6 sodium ethanolate 
• 107-99-3 2-(dimethylamino)ethyl chloride 
• 1137-42-4 4-Hydroxybenzophenone 
• 4584-46-7 (2-chloroethyl)dimethylamine hydrochloride 
• 1391906-41-4 2-(dimethylamino)ethyl ethyl carbonate 
• 108-01-0 2-(N,N-dimethylamino)ethanol 
• 105-58-8 Diethyl carbonate 
• 101665-51-4 Sodium; 4-benzoyl-phenolate 

Downstream Products

• 4258-30-4 4-(2-dimethylamino-ethoxy)-benzhydrol 
• 51360-32-8 1-Phenyl-1-phenylethylene 
• 10540-29-1 tamoxifen 
• 748-97-0 1-(4-(2-(dimethylamino)ethoxy)phenyl)-1,2-diphenylbutan-1-ol 
• 556834-75-4 (E,Z)-3-[4-(2-dimethylaminoethoxy)phenyl]-2,3-diphenylacrylonitrile 
• 141854-25-3 1,2-diphenyl-1-[4-[2-(N,N-dimethylamino)ethoxy]phenyl]butane-1,4-diol 
• 10540-29-1 tamoxifen 
• 556834-76-5 (E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-one 
• 556834-77-6 (E,Z)-4-[4-(2-dimethylaminoethoxy)phenyl]-3,4-diphenyl-but-3-en-2-ol 
• 13002-65-8 (E)-tamoxifen 

Relevant academic research and scientific papers

Mustard Carbonate Analogues as Sustainable Reagents for the Aminoalkylation of Phenols

N,N-dialkyl ethylamine moiety can be found in numerous scaffolds of macromolecules, catalysts, and especially pharmaceuticals. Common synthetic procedures for its incorporation in a substrate relies on the use of a nitrogen mustard gas or on multistep syntheses featuring chlorine hazardous/toxic chemistry. Reported herein is a one-pot synthetic approach for the easy introduction of aminoalkyl chain into different phenolic substrates through dialkyl carbonate (β-aminocarbonate) chemistry. This new direct alcohol substitution avoids the use of chlorine chemistry, and it is efficient on numerous pharmacophore scaffolds with good to quantitative yield. The cytotoxicity via MTT of the β-aminocarbonate, key intermediate of this synthetic approach, was also evaluated and compared with its alcohol precursor.

Alkylating method of 4-hydroxybenzophenone

The invention discloses an alkylating method of 4-hydroxybenzophenone. The method is characterized in that an alkylating agent and 4-hydroxybenzophenone are alkylated in the presence of anion exchangeresin and phase transfer catalyst; then simple post-processing is carried out after reaction so as to obtain the high-yield and high-purity target product. According to the method, the reaction system is capable of improving the alkylating reaction performance through the anion exchange resin and the phase transfer catalyst, so that the byproducts are greatly decreased while the reaction is spedup, and as a result, the difficulty in post-processing and purifying can be reduced, and an alkylating product whose purity is 99% or more can be obtained through simple post-processing. With the adoption of the method, the problems of column chromatography and purifying, long reaction time and low yield in the prior art can be solved; the method is applicable to industrial production. The formulais shown in the description.

Design and synthesis of triarylacrylonitrile analogues of tamoxifen with improved binding selectivity to protein kinase C

The clinical selective estrogen receptor modulator tamoxifen is also a modest inhibitor of protein kinase C, a target implicated in several untreatable brain diseases such as amphetamine abuse. This inhibition and tamoxifen's ability to cross the blood br

POLYMORPHIC FORM OF TOREMIFENE CITRATE AND PROCESS FOR ITS PREPARATION

The present invention provides a polymorphic form of toremifene citrate and processes for its preparation. It also relates to an improved process for the preparation of the Z isomer of the toremifene base, free of E isomer, and its pharmaceutically acceptable salts.

Wittig-Horner approach for the synthesis of tamoxifen

A stereoselective synthesis of Z-tamoxifen, a tetra-substituted alkene with antiestrogenic activity, is described. The Wittig-Horner reaction has been employed as the key step to establish the olefin stereochemistry. Copyright Taylor & Francis, Inc.

Flexible estrogen receptor modulators: Design, synthesis, and antagonistic effects in human MCF-7 breast cancer cells

Although many series of estrogen receptor antagonists continue to be produced, the majority are direct structural analogues of existing modulators. To examine the tolerance of the estrogen receptor toward flexible ligands, a series of novel flexible estrogen receptor antagonists were prepared and their antiproliferative effects on human MCF-7 breast tumor cells investigated. Each of these compounds deviated from the traditional triphenylethylene backbone associated with common tamoxifen analogues through the introduction of a flexible methylene (benzylic) spacing group between one of the aryl rings and the ethylene group and through variations in the basic side chain moiety. The compounds prepared, when assayed in conjunction with a tamoxifen standard, demonstrated high potency in antiproliferative assays against an MCF-7 human breast cancer cell line with low cytotoxicity and high binding affinity. A computational study was undertaken to investigate the compounds' potential interactions with specific residues within the human estrogen receptor α ligand-binding domain (ER-LBD), predicting these compounds bind in an antiestrogenic fashion within the ER-LBD and interact with those important residues previously identified in the structures of ER-LBD agonist/antagonist cocrystals. These compounds further illustrate the eclectic nature of the estrogen receptor in terms of ligand flexibility tolerance.

Synthesis of Tamoxifen and 4-Hydroxytamoxifen using Super-base-metalated Propylbenzene

Propylbenzene is metalated regioselectively at the α-carbon using the n-BuLi-t-BuOK-TMEDA super-base combination; the resulting carbanion condenses with functionalised benzophenones to provide direct syntheses of tamoxifen and 4-hydroxytamoxifen.

Crossed Coupling of Functionalised Ketones by Low Valent Titanium (The McMurry Reaction): A New Stereoselective Synthesis of Tamoxifen

Low valent titanium-mediated crossed coupling of substitued benzophenones of the 4-XPhCOPh, where X = MeO, ClCH2CH2O, BrCH2CH2O, CF3C6H4O, HO, and Me2NCH2CH2O, with propiophenone affords the corresponding but-1-enes in high yield with a marked preponderance of the Z-isomer in most cases.Remarkably, when X = OH the E:Z ratio is 9:1.The value of this method is illustrated by simple syntheses of (Z)-1-phenyl>-1,2-diphenylbut-1-ene (Tamoxifen) a drug widely used in the treatment of eostrogen-dependent breast tumors.