147323-02-2

Basic information

• Product Name: Phenol, 4-[1-[4-(2-bromoethoxy)phenyl]-2-phenyl-1-butenyl]-
• CAS NO: 147323-02-2
• Molecular Formula: C24H23BrO2
• Molecular Weight: 423.349
• Mol File: 147323-02-2.mol
• Article Data: 7

Chemical Properties

• CAS DataBase Reference: Phenol, 4-[1-[4-(2-bromoethoxy)phenyl]-2-phenyl-1-butenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Phenol, 4-[1-[4-(2-bromoethoxy)phenyl]-2-phenyl-1-butenyl]-(147323-02-2)
• EPA Substance Registry System: Phenol, 4-[1-[4-(2-bromoethoxy)phenyl]-2-phenyl-1-butenyl]-(147323-02-2)

Safety Data

• Hazardous Substances Data: 147323-02-2(Hazardous Substances Data)

Upstream product

• 93-55-0 1-phenyl-propan-1-one 
• 91221-46-4 1,1-bis(4-hydroxyphenyl)-2-phenyl-1-butene 
• 106-93-4 ethylene dibromide 
• 589-10-6 phenoxyethyl bromide 
• 99-96-7 4-hydroxy-benzoic acid 
• 611-99-4 4,4'-Dihydroxybenzophenone 
• 185223-77-2 [4-(2-Bromo-ethoxy)-phenyl]-[4-(tetrahydro-pyran-2-yloxy)-phenyl]-methanone 
• 52191-15-8 4-(2-bromoethyloxy)benzaldehyde 
• 123-08-0 4-hydroxy-benzaldehyde 
• 106-41-2 4-bromo-phenol 
• 36603-49-3 4-(tetrahydropyran-2'-yloxy)-1-bromobenzene 
• 103-65-1 phenylpropane 
• 850256-21-2 E/Z-1-[4-(2-bromoethoxy)phenyl]-1-(4-methoxyphenyl)-2-phenylbut-1-ene 
• 79578-62-4 (4-(2-bromoethoxy)phenyl)(4-hydroxyphenyl)methanone 

Downstream Products

• 141777-00-6 (E,Z)-4-<1-(p-hydroxyphenyl)-2-phenyl-1-butenyl>phenoxyacetic acid 
• 185223-81-8 (4-{(E)-1-[4-(2-Bromo-ethoxy)-phenyl]-2-phenyl-but-1-enyl}-phenoxy)-acetic acid 
• 952702-47-5 4-(1-(4-(2-(6-aminohexylamino)ethoxy)phenyl)-2-phenylbut-1-enyl)phenol 
• 1217237-98-3 4-(1-(4-(2-aminoethoxy)phenyl)-2-phenylbut-1-en-1-yl)phenol 
• 114828-90-9 trans-Endoxifen 
• 68047-06-3 Z-1-<4-(2-dimethylaminoethoxy)phenyl>-1-(4-hydroxyphenyl)-2-phenyl-1-butene 
• 174592-47-3 trans 4-hydroxytamoxifen 
• 671791-76-7 E/Z-N-[2-hydroxy-5-({2-[(2-{4-[1-(4-hydroxyphenyl)-2-phenylbut-1-enyl]phenoxy}ethyl)methylamino]ethoxyimino}methyl)benzamide]doxorubicin 
• 850256-34-7 E/Z-1-{4-[2-({2-[2-(2-aminooxyethoxy)ethoxy]ethyl}methylamino)ethoxy]phenyl}-1-(4-hydroxyphenyl)-2-phenylbutene 
• 850256-33-6 E/Z-1-[4-(2-{[2-(2-aminooxyethoxy)ethyl]methylamino}ethoxy)phenyl]-1-(4-hydroxyphenyl)-2-phenylbutene 
• 850256-24-5 E/Z-1-(4-{2-[(2-aminooxyethyl)methylamino]ethoxy}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 
• 68392-35-8 4-hydroxytamoxifen 

Relevant articles and documents

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Design, Synthesis, and Biological Evaluation of Doxorubicin-Formaldehyde Conjugates Targeted to Breast Cancer Cells

The anthracycline antitumor drug doxorubicin (DOX) has been utilized for decades as a broad-spectrum chemotherapeutic. Recent literature evidence documents the role of formaldehyde in the cytotoxic mechanism, and anthracycline-formaldehyde conjugates possess substantially enhanced activity in vitro and in vivo. Targeting a doxorubicin-formaldehyde conjugate specifically to cancer cells may provide a more efficacious chemotherapeutic. The design and 11-step synthesis of doxorubicin-formaldehyde conjugates targeted to the estrogen receptor, which is commonly overexpressed in breast cancer cells, are reported. The formaldehyde is incorporated in a masked form as an N-Mannich linkage between doxorubicin and salicylamide. The salicylamide triggering molecule, previously developed to release the doxorubicin-formaldehyde active metabolite, is tethered via derivatized ethylene glycols to an E and Z mixture of 4-hydroxytamoxifen. The targeting group, E/Z-4-hydroxytamoxifen, was selected for its ability to tightly bind the estrogen receptor and antiestrogen binding sites. The targeted doxorubicin-formaldehyde conjugates' estrogen receptor binding and in vitro growth inhibition were evaluated as a function of tether length. The lead compound, DOX-TEG-TAM, bearing a triethylene glycol tether, binds the estrogen receptor with a binding affinity of 2.5% relative to E/Z-4-hydroxytamoxifen and inhibits the growth of four breast cancer cell lines with 4-fold up to 140-fold enhanced activity relative to doxorubicin.