103628-22-4

Usage

Uses

Used in Pharmaceutical Industry:
1-[4-(2-Chloroethoxy)phenyl]-2-ethyl-2-phenylethanone is used as a chemical intermediate for the synthesis of a metabolite of Tamoxifen, a drug used in the treatment of breast cancer. Its role in the synthesis process is crucial for producing the active compound that can effectively target cancer cells and manage the disease.

InChI:InChI=1/C18H19ClO2/c1-2-17(14-6-4-3-5-7-14)18(20)15-8-10-16(11-9-15)21-13-12-19/h3-11,17H,2,12-13H2,1H3

Upstream product

• 90-27-7 2-Phenylbutyric acid 
• 622-86-6 2-chloroethoxybenzene 
• 122-99-6 2-Phenoxyethanol 
• 36854-57-6 2-Phenylbutyryl chloride 
• 108-95-2 phenol 

Downstream Products

• 129921-03-5 (E)-1-(4-bromophenyl)-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butene 
• 116057-72-8 1-[4-(2-Chloro-ethoxy)-phenyl]-1-(4-iodo-phenyl)-2-phenyl-butan-1-ol 
• 129920-99-6 (E)-1-bromo-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butene 
• 129921-00-2 (Z)-1-bromo-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butene 
• 129921-02-4 N-<(Z)-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butenyl>-N-phenyltrifluoromethanesulfonamide 
• 129921-01-3 N-<(E)-1-<4-(2-chloroethoxy)phenyl>-2-phenyl-1-butenyl>-N-phenyltrifluoromethanesulfonamide 
• 103628-16-6 Z-1-<4-(2-chloroethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 
• 103628-17-7 E-1-<4-(2-chloroethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 
• 116057-73-9 (E)-1-<4-(2-chloroethoxy)phenyl>-1-(4-iodophenyl)-2-phenyl-1-butene 
• 116057-74-0 (Z)-1-<4-(2-chloroethoxy)phenyl>-1-(4-iodophenyl)-2-phenyl-1-butene 
• 116057-66-0 4-Iodotamoxifen 
• 10540-29-1 tamoxifen 
• 119757-57-2 (E,Z)-1-<4-(2-chloroethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 
• 1350660-46-6 (E/Z)-4-(1-{4-[2-(hexylamino)ethoxy]phenyl}-2-phenylbut-1-en-1-yl)phenol 

Relevant academic research and scientific papers

Development of an efficient and stereoselective manufacturing route to idoxifene

A literature route to 1-(2-{4-[(E)-1-(4-iodophenyl)-2-phenyl-but-1-enyl]phenoxy}ethyl)pyrrolidine (idoxifene) has been modified to tackle various scale-up issues and provide initial supplies. A new highly efficient, robust, and stereoselective manufacturing route is described in detail. This route involves diastereoselective synthesis of tertiary alcohol (1RS,2SR)-1-(4-iodophenyl)-2-phenyl-1-[4-(2-pyrrolidin-1-yl-ethoxy)phenyl]butan- 1-ol by Grignard addition to the ketone 1-(4-iodophenyl)-2-phenyl-1-butanone followed by derivatisation and stereoselective syn elimination to provide idoxifene in excellent yield and geometric purity. Evaluation of a more direct route to idoxifene using a McMurry low-valent titanium coupling reaction is also described.

Novel compounds that reverse the disease phenotype in Type 2 Gaucher disease patient-derived cells

Gaucher disease (GD) results from inherited mutations in the lysosomal enzyme β-glucocerobrosidase (GCase). Currently available treatment options for Type 1 GD are not efficacious for treating neuronopathic Type 2 and 3 GD due to their inability to cross the blood-brain barrier. In an effort to identify small molecules which could be optimized for CNS penetration we identified tamoxifen from a high throughput phenotypic screen on Type 2 GD patient-derived fibroblasts which reversed the disease phenotype. Structure activity studies around this scaffold led to novel molecules that displayed improved potency, efficacy and reduced estrogenic/antiestrogenic activity compared to the original hits. Here we present the design, synthesis and structure activity relationships that led to the lead molecule Compound 31.

NOVEL FUNCTIONALIZED N,N-DIALKYLAMINO PHENYL ETHERS AND THEIR METHOD OF USE

Pharmaceutical compositions of the invention comprise functionalized N,N-dialkylamino phenyl ethers derivatives having a disease-modifying action in the treatment of diseases associated with lysosomal storage dysfunction that include Gaucher's disease, and any disease or condition involving lysosomal storage dysfunction.

TETRASUBSTITUTED ALKENE COMPOUNDS AND THEIR USE

Disclosed herein are compounds, or pharmaceutically acceptable salts thereof, and methods of using the compounds for treating breast cancer by administration to a subject in need thereof a therapeutically effective amount of the compounds or pharmaceutically acceptable salts thereof. The breast cancer may be an ER-positive breast cancer and/or the subject in need of treatment may express a mutant ER-α protein.

Design and synthesis of tamoxifen derivatives as a selective estrogen receptor down-regulator

We designed and synthesized an estrogen receptor (ER) down-regulator (5), which is a derivative of tamoxifen with a long alkyl side chain. Compound 5 effectively reduced ER protein levels in MCF-7 cells and had an antagonistic effect.

Endoxifen is a new potent inhibitor of PKC: A potential therapeutic agent for bipolar disorder

Protein kinase C (PKC) plays a major role in regulation of both pre and postsynaptic neurotransmission. Excessive activation of PKC results in symptoms related to bipolar disorder. Tamoxifen, a widely used breast cancer drug is known to inhibit PKC and demonstrate antimanic properties in human. We describe herein the synthesis of endoxifen, a tamoxifen active metabolite and compared its PKC inhibitory activity with that of tamoxifen. Endoxifen exhibited fourfold higher potency compared to tamoxifen.

MRI CONTRAST AGENTS FOR DIAGNOSIS AND PROGNOSIS OF TUMORS

The invention relates to bifunctional conjugates comprising a receptor ligand moiety and a metal binding moiety and complexes thereof with paramagnetic lanthanide or transition metals, and to the use of the metal complexes as contrast agents in magnetic resonance imaging (MRI) of tumors and other abnormalities.

The total synthesis of a technetium chelate - Tamoxifen complex

A potential agent for imaging breast cancer has been synthesized by derivatization of the anti-estrogen tamoxifen. A multistep synthesis was required to conjugate a technetium chelate to tamoxifen in such a fashion that the biodistribution of the complex should mimic that of the parent compound.

The Use of the Perfluorotolyl Protecting Group in the Synthesis of Pure Z and E Isomers of 4-Hydroxytamoxifen -1-(4-hydroxyphenyl)-2-phenyl-1-butene>

The perfluorotolyl protecting group has been used in the synthesis of pure Z and E isomers of 4-hydroxytamoxifen (4a), a potent metabolite of the anticancer drug, tamoxifen (1a). 4-(Perfluorotolyloxy)phenyl magnesium bromide underwent addition to the carbonyl group of the easily prepared versatile ketone, 1--2-phenyl-1-butanone (7), without affecting the chloroethoxy group.Acid catalysed dehydration of the resulting carbinol gave a 1:1 mixture of isomeric ethers, (6a) and (6b), that were easily separated by chromatography and respectively converted to the Z (4a) and E (4b) isomers of 4-hydroxytamoxifen.The property of the perfluorotolyl function in enabling the separation of geometrical isomers is attributed to a combination of its lipophilicity and electron withdrawal.