109091-08-9

Basic information

• Product Name: (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone
• Synonyms: (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone
• CAS NO: 109091-08-9
• Molecular Formula: C₁₇H₁₈O₅
• Molecular Weight: 302.32182
• Mol File: 109091-08-9.mol
• Article Data: 14

Chemical Properties

• Appearance: /
• CAS DataBase Reference: (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone(CAS DataBase Reference)
• NIST Chemistry Reference: (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone(109091-08-9)
• EPA Substance Registry System: (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone(109091-08-9)

Safety Data

• Hazardous Substances Data: 109091-08-9(Hazardous Substances Data)

Usage

Description

(4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone is a synthetic organic compound characterized by its two aromatic rings connected to a central ketone group. (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone features a unique arrangement of methoxy groups, which are known for their diverse biological and pharmacological properties. Its structure and functional groups make it a valuable building block in the synthesis of more complex organic molecules, particularly in medicinal chemistry. The specific positioning of methoxy groups in this compound may endow it with potential antioxidant, antibacterial, or antifungal activities, highlighting its potential for further research and development.

Uses

Used in Medicinal Chemistry:
(4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone is used as a building block for the synthesis of complex organic molecules in the field of medicinal chemistry. Its unique arrangement of methoxy groups and aromatic rings provides a versatile starting point for the development of new pharmaceutical compounds.
Used in Antioxidant Applications:
In the pharmaceutical industry, (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone is used as a potential antioxidant agent. The presence of methoxy groups may contribute to its antioxidant properties, making it a candidate for further research into its ability to protect cells from oxidative stress and related diseases.
Used in Antibacterial and Antifungal Applications:
(4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone is also used as a potential antibacterial and antifungal agent. (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone's structure, particularly the methoxy groups, may impart these activities, which could be beneficial in the development of new antimicrobial drugs to combat resistant infections.
Used in Chemical Research:
In the field of chemical research, (4-Methoxyphenyl)(3,4,5-triMethoxyphenyl)Methanone serves as a model compound for studying the effects of methoxy group positioning on the biological and pharmacological properties of organic molecules. This research can provide valuable insights into the design of new compounds with specific therapeutic applications.

Upstream product

• 54808-44-5 4-hydroxy-3,5,4'-trimethoxy-benzophenone 
• 77-78-1 dimethyl sulfate 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 100-66-3 methoxybenzene 
• 118-41-2 Eudesmic acid 
• 25245-29-8 5-iodo-1,2,3-trimethoxybenzene 
• 67-66-3 chloroform 
• 5720-07-0 4-methoxyphenylboronic acid 
• 213596-33-9 2-(4-methoxyphenyl)-5,5-dimethyl-1,3,2-dioxaborolane 
• 50978-45-5 3-oxobenzo[d]isothiazole-2(3H)-carbaldehyde 1,1-dioxide 
• 201230-82-2 carbon monoxide 
• 86-81-7 3,4,5-trimethoxy-benzaldehyde 
• 123-11-5 4-methoxy-benzaldehyde 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 

Downstream Products

• 1206882-87-2 3,4,5-trihydroxy-4'-methoxybenzophenone 
• 1067880-32-3 1,2,3-trimethoxy-5-(1-(4-methoxyphenyl)vinyl)benzene 
• 141172-41-0 (4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanol 
• 101747-36-8 1,2,3-trimethoxy-5-(4-methoxybenzyl)benzene 

Relevant articles and documents

Pd/C in Propylene Carbonate: A Sustainable Catalyst–Solvent System for the Carbonylative Suzuki–Miyaura Cross-Coupling Using N-Formylsaccharin as a CO Surrogate

This work documents the first Pd/C-catalyzed carbonylative Suzuki–Miyaura cross-coupling of aryl iodides with N-formylsaccharin as a CO surrogate. In contrast to previous reaction protocols, which make use of toxic and hazardous solvents, the reaction could be advantageously performed in propylene carbonate as an environmentally benign and sustainable polar aprotic solvent. A range of biaryl ketones, including (4-methoxyphenyl)(3,4,5-trimethoxyphenyl)methanone, an antineoplastic belonging to the phenstatin family, could be synthesized under cocatalyst-free, additive-free and ligand-free conditions. The Pd/C could be recycled up to five times under CO surrogacy with only a marginal decrease in catalytic activity. The reaction could also be scaled up to gram-scale syntheses.

A facile and efficient method for deprotection of thioketones

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Synthesis and biological evaluation of 1‐(Diarylmethyl)‐1h‐1,2,4‐triazoles and 1‐(diarylmethyl)‐1h‐imidazoles as a novel class of anti‐mitotic agent for activity in breast cancer

We report the synthesis and biochemical evaluation of compounds that are designed as hybrids of the microtubule targeting benzophenone phenstatin and the aromatase inhibitor letrozole. A preliminary screening in estrogen receptor (ER)‐positive MCF‐7 breast cancer cells identified 5‐((2H‐1,2,3‐triazol‐1‐yl)(3,4,5‐trimethoxyphenyl)methyl)‐2‐methoxyphenol 24 as a potent antiproliferative compound with an IC50 value of 52 nM in MCF‐7 breast cancer cells (ER+/PR+) and 74 nM in triple‐negative MDA‐MB‐231 breast cancer cells. The compounds demonstrated significant G2/M phase cell cycle arrest and induction of apoptosis in the MCF‐7 cell line, inhibited tubulin polymerisation, and were selective for cancer cells when evaluated in non-tumorigenic MCF‐10A breast cells. The immunofluorescence staining of MCF‐7 cells confirmed that the compounds targeted tubulin and induced multinucleation, which is a recognised sign of mitotic catastrophe. Computational docking studies of compounds 19e, 21l, and 24 in the colchicine binding site of tubulin indicated potential binding conformations for the compounds. Compounds 19e and 21l were also shown to selectively inhibit aromatase. These compounds are promising candidates for development as antiproliferative, aromatase inhibitory, and microtubule‐disrupting agents for breast cancer.

Ni-Catalyzed cross-coupling reactions of N-acylpyrrole-type amides with organoboron reagents

The catalytic conversion of amides to ketones is highly desirable yet challenging in organic synthesis. We herein report the first Ni/bis-NHC-catalyzed cross-coupling of N-acylpyrrole-type amides with arylboronic esters to obtain diarylketones. This method is facilitated by a new chelating bis-NHC ligand. The reaction tolerates diverse functional groups on both arylamide and arylboronic ester partners including sensitive ester and ketone groups.