4390-94-7

Basic information

• Product Name: 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE
• Synonyms: 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE;alpha-ethyldeoxyanisoin;6-METHOXY-2-(4-METHOXYPHENYL) 98%;1,2-bis(4-methoxyphenyl)butan-1-one
• CAS NO: 4390-94-7
• Molecular Formula: C₁₈H₂₀O₃
• Molecular Weight: 284.3496
• Mol File: 4390-94-7.mol
• Article Data: 10

Chemical Properties

• Melting Point: 58-60 °C
• Boiling Point: 428.1 °C at 760 mmHg
• Flash Point: 204.5 °C
• Appearance: /
• Density: 1.079 g/cm³
• CAS DataBase Reference: 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE(CAS DataBase Reference)
• NIST Chemistry Reference: 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE(4390-94-7)
• EPA Substance Registry System: 4'-METHOXY-2-P-METHOXYPHENYLBUTYROPHENONE(4390-94-7)

Safety Data

• Hazardous Substances Data: 4390-94-7(Hazardous Substances Data)

Usage

General Description

4'-Methoxy-2-p-methoxyphenylbutyrophenone is a chemical compound that has the molecular formula C21H23NO3. It is a synthetic compound that belongs to the family of butyrophenone derivatives and is commonly used as a neuroleptic in the treatment of various psychiatric disorders such as schizophrenia and bipolar disorder. 4'-Methoxy-2-p-methoxyphenylbutyrophenone acts as a dopamine antagonist, meaning it blocks the action of the neurotransmitter dopamine in the brain, which helps to alleviate symptoms of psychosis and other mental health conditions. Additionally, 4'-methoxy-2-p-methoxyphenylbutyrophenone has also been studied for its potential use as an anti-inflammatory and analgesic agent, showing promise in reducing pain and inflammation in experimental models. Overall, this compound has significant pharmacological effects and is an important tool in the treatment of various neurological and psychiatric conditions.

Upstream product

• 97-94-9 triethyl borane 
• 1226-42-2 1,2-bis(4-methoxyphenyl)-1,2-ethanedione 
• 90-96-0 bis(p-methoxyphenyl)methanone 
• 4693-91-8 4-methoxyphenyl-acetic chloride 
• 100-66-3 methoxybenzene 
• 53530-36-2 (Z)-3,4-bis(4-methoxyphenyl)hex-2-ene 
• 53530-36-2 (E)-3,4-bis(4-methoxyphenyl)hex-2-ene 
• 10028-15-6 ozone 
• 64-19-7 acetic acid 
• 75-00-3 chloroethane 
• 412017-89-1 2-amino-1,1-bis-(4-methoxy-phenyl)-butan-1-ol 
• 60-29-7 diethyl ether 
• 93902-86-4 1,1-bis-(4-methoxy-phenyl)-but-1-ene 
• 7553-56-2 iodine 

Downstream Products

• 130-79-0 Diethylstilbestrol dimethyl ether 
• 855238-75-4 1,2-bis-(4-methoxy-phenyl)-1-phenyl-butan-1-ol 
• 76579-69-6 1,2-bis-(4-hydroxy-phenyl)-butan-1-one 
• 6346-06-1 1-chloro-1,2-bis-(4-methoxy-phenyl)-but-1-ene 
• 82333-60-6 1,1,2-tris(4-methoxyphenyl)but-1-ene 
• 67566-92-1 6,7-Bis-(4-methoxyphenyl)-1-nonen-6-ol 
• 343844-60-0 methyl 3-hydroxy-3,4-bis(4-methoxyphenyl)hexanoate 
• 74536-71-3 (Z)-methyl 3,4-bis(4-methoxyphenyl)-2-hexanoate 
• 74536-73-5 methyl erythro-3,4-bis(4-hydroxyphenyl)hexanoate 

Relevant articles and documents

Novel carbamοyloxy analogues of tamoxifen: Synthesis, molecular docking and bioactivity evaluation

Background: Tamoxifen (TAM), a non-steroidal antiestrogen, constitutes the endocrine treatment of choice against breast cancer. Since its inauguration, substantial effort has been devoted towards the design and synthesis of TAM’s analogues aiming to improve its bioactivity and reveal their structure-activity relationship. Objective: One of the most studied synthetic features of TAM’s structure is the ether side chain, which is strongly related to its positioning into the active site of the Estrogen Receptors (ERα and ERβ). Herein, we present the application of a straightforward route for the efficient synthesis of selected novel carbamoyloxy analogues of TAM and the evaluation of their respective binding affinities to the Estrogen Receptors α and β. Methods: A one-pot reaction was applied for the construction of TAM’s triarylethylene core moiety, which subsequently was derivatized to provide efficiently the target carbamoyloxy analogues of TAM. The Z and E isomers of the latter were separated using RP-HPLC-UV and their binding affinities to ERα and ERβ were measured. Results: Among all compounds synthesized, the dimethyl derivative was determined as the most potent for both receptors, displaying binding affinity values comparable to TAM, though the Z-diethyl analogue maintained substantial affinity to both ERs. The aforementioned results were further studied by theoretical calculations and molecular modelling to delineate a concordance among calculations and biological activity. Conclusion: Approach applied herein permitted the extraction of a useful structure-activity relationship correlation pattern highlighting the importance of a chemically stabilized tamoxifen side chain.

Structure-function relationships of estrogenic triphenylethylenes related to endoxifen and 4-hydroxytamoxifen

Estrogens can potentially be classified into planar (class I) or nonplanar (class II) categories, which might have biological consequences. 1,1,2-Triphenylethylene (TPE) derivatives were synthesized and evaluated against 17β-estradiol (E2) for their estrogenic activity in MCF-7 human breast cancer cells. All TPEs were estrogenic and, unlike 4-hydroxytamoxifen (4OHTAM) and Endoxifen, induced cell growth to a level comparable to that of E2. All the TPEs increased ERE activity in MCF-7:WS8 cells with the order of potency as followed: E2 > 1,1-bis(4,4′-hydroxyphenyl)-2-phenylbut-1-ene (15) > 1,1,2-tris(4-hydroxyphenyl)but-1-ene (3) > Z 4-(1-(4-hydroxyphenyl)-1- phenylbut-1-en-2-yl)phenol (7) > E 4-(1-(4-hydroxyphenyl)-1-phenylbut-1-en-2- yl)phenol (6) > Z(4-(1-(4-ethoxyphenyl)-1-(4-hydroxyphenyl)but-1-en-2-yl) phenol (12) > 4-OHTAM. Transient transfection of the ER-negative breast cancer cell line T47D:C4:2 with wild-type ER or D351G ER mutant revealed that all of the TPEs increased ERE activity in the cells expressing the wild-type ER but not the mutant, thus confirming the importance of Asp351 for ER activation by the TPEs. The findings confirm E2 as a class I estrogen and the TPEs as class II estrogens. Using available conformations of the ER liganded with 4OHTAM or diethylstilbestrol, the TPEs optimally occupy the 4OHTAM ER conformation that expresses Asp351.

Synthesis and biological evaluation of stilbene-based pure estrogen antagonists

The nonsteroidal estrogen diethylstilbestrol can be converted into potent antiestrogens devoid of agonist activity by introduction of side chains with appropriate functional groups. Replacement of one of the ethyl substituents in diethylstilbestrol by side chains with functional groups converted this potent estrogen into pure antiestrogens with the potential for the treatment of breast cancer. These agents completely suppressed estrogen receptor-mediated gene activation and inhibited the growth of estrogen-sensitive MCF-7 breast cancer cells in submicromolar concentrations. The most potent derivative displayed similar activity as fulvestrant (ICI 182,780) in vitro and in the mouse uterine weight test. Obviously, the stilbene structure can act as a substitute for estradiol in the development of pure estrogen antagonists.