22699-97-4

Basic information

• Product Name: Methanone, (3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)-
• Synonyms: Methanone, (3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)-;(3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)methanone
• CAS NO: 22699-97-4
• Molecular Formula: C₁₈H₂₀O₆
• Molecular Weight: 332.35
• Mol File: 22699-97-4.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 490.3°Cat760mmHg
• Flash Point: 216.1°C
• Appearance: /
• Density: 1.155g/cm³
• Vapor Pressure: 9.29E-10mmHg at 25°C
• Refractive Index: 1.534
• CAS DataBase Reference: Methanone, (3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)-(CAS DataBase Reference)
• NIST Chemistry Reference: Methanone, (3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)-(22699-97-4)
• EPA Substance Registry System: Methanone, (3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)-(22699-97-4)

Safety Data

• Hazardous Substances Data: 22699-97-4(Hazardous Substances Data)

Usage

InChI:InChI=1/C18H20O6/c1-20-13-7-6-11(8-14(13)21-2)17(19)12-9-15(22-3)18(24-5)16(10-12)23-4/h6-10H,1-5H3

Upstream product

• 91-16-7 1,2-dimethoxybenzene 
• 4521-61-3 3,4,5-Trimethoxybenzoyl chloride 
• 118-41-2 Eudesmic acid 
• 2675-79-8 1-bromo-3,4,5-trimethoxybenzene 
• 22792-13-8 4-(3’,4’-dimethoxybenzoyl)morpholine 
• 7446-70-0 aluminium trichloride 
• 93-07-2 Veratric acid 
• 3535-37-3 3,4-dimethoxybenzoic acid chloride 
• 874812-62-1 2-methoxy-5-(3,4,5-trimethoxybenzoyl)phenyl 2-chloroacetate 
• 30287-15-1 2-methoxyphenyl 2-chloroacetate 
• 90-05-1 2-methoxy-phenol 
• 77-78-1 dimethyl sulfate 
• 203448-32-2 phenstatin 

Downstream Products

• 102473-59-6 3-(3,4-dimethoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propionic acid ethyl ester 
• 944645-51-6 (3,4-dimethoxyphenyl)(3,4,5-trimethoxyphenyl)methanol 
• 129150-01-2 1,1-(1,2-Benzenediyldithio)-4-(3,4,5-trimethoxyphenyl)-6,7-dimethoxy-1,2,3,4-tetrahydronaphthalene 
• 129149-99-1 3-(3,3',4,4',5'-Pentamethoxybenzhydryl)-2-ethylidene-1,3-benzodithiole 
• 129150-02-3 4-(3,4,5-Trimethoxyphenyl)-6,7-dimethoxy-1-tetralone 
• 129150-16-9 3-(3,4-Dimethoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-propan-1-ol 
• 129150-00-1 2-(3,3',4,4',5'-Pentamethoxybenzhydryl)ethanal 
• 96266-93-2 trans-5,6-Dimethoxy-1-(3,4,5-trimethoxy-phenyl)-indanon-⁽³⁾-essigsaeure-⁽²⁾ 
• 1178-16-1 <3.4.5.3'.4'-Pentamethoxy-benzhydryliden>-bernsteinsaeure 
• 1089710-80-4 <3.4.5.3'.4'-Pentamethoxy-benzhydryliden>-bernsteinsaeure 
• 129150-14-7 (Z)-3-(3,4-Dimethoxy-phenyl)-3-(3,4,5-trimethoxy-phenyl)-acrylic acid ethyl ester 
• 2962-78-9 cis-6,7-Dimethoxy-4-oxo-1-(3,4,5-trimethoxy-phenyl)-tetrahydro-<2>naphthoesaeure-aethylester 
• 2962-79-0 trans-5,6,7-Trimethoxy-4-oxo-1-(3,4-dimethoxy-phenyl)-tetrahydro-<2>naphthoesaeure 
• 3274-78-0 cis-6,7-Dimethoxy-4-oxo-1-(3,4,5-trimethoxy-phenyl)-tetrahydro-<2>naphthoesaeure-methylester 

Relevant articles and documents

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.

Synthesis and biological evaluation of phenstatin metabolites

Previous investigations on the incubation of phenstatin with rat and human microsomal fractions revealed the formation of nine main metabolites. The structures of eight of these metabolites have been now confirmed by synthesis and their biological properties have been reported. Eaton's reagent was utilized as a convenient condensing agent, allowing, among others, a simple multigram scale preparation of phenstatin. Synthesized metabolites and related compounds were evaluated for their antiproliferative activity in the NCI-60 cancer cell line panel, and for their effect on microtubule assembly. Metabolite 23 (2′-methoxyphenstatin) exhibited the most potent in vitro cytotoxic activity: inhibition of the growth of K-562, NCI-H322M, NCI-H522, KM12, M14, MDA-MB-435, NCI/ADR-RES, and HS 578T cell lines with GI50 values 50 = 3.2 μM vs 15.0 μM) and induced G2/M arrest in murine leukemia DA1-3b cells. The identification of this active metabolite led to the design and synthesis of analogs with potent in vitro cytotoxicity and inhibition of microtubule assembly.

Synthesis of phenstatin and prodrugs thereof

A newly discovered antineoplastic compound denominated “phenstatin” is herein described as are synthetic methods for producing phenstatin and the active prodrug thereof. Phenstatin was converted to the sodium phosphate prodrug (3d) by a dibenzylphosphite