33495-30-6

Basic information

• Product Name: Ethanone, 1-[2-(benzoyloxy)-4,6-dimethoxyphenyl]-
• CAS NO: 33495-30-6
• Molecular Formula: C17H16O5
• Molecular Weight: 300.311
• Mol File: 33495-30-6.mol
• Article Data: 5

Chemical Properties

• CAS DataBase Reference: Ethanone, 1-[2-(benzoyloxy)-4,6-dimethoxyphenyl]-(CAS DataBase Reference)
• NIST Chemistry Reference: Ethanone, 1-[2-(benzoyloxy)-4,6-dimethoxyphenyl]-(33495-30-6)
• EPA Substance Registry System: Ethanone, 1-[2-(benzoyloxy)-4,6-dimethoxyphenyl]-(33495-30-6)

Safety Data

• Hazardous Substances Data: 33495-30-6(Hazardous Substances Data)

Upstream product

• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 98-88-4 benzoyl chloride 
• 500-99-2 3,5-dimethoxyphenol 
• 480-66-0 2,4,6-trihydroxyacetophenone 

Downstream Products

• 33507-94-7 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione 
• 21392-57-4 Dimethyl-chrysin 
• 124259-94-5 3,5-dimethoxy-2-(5-phenyl-1⁽²⁾H-pyrazol-3-yl)-phenol 
• 124259-95-6 2-(1,5-diphenyl-1H-pyrazol-3-yl)-3,5-dimethoxyphenol 
• 124259-96-7 3,5-Dimethoxy-2-(5-phenyl-1-p-tolyl-1H-pyrazol-3-yl)-phenol 
• 124259-97-8 2-[1-(2,4-Dinitro-phenyl)-5-phenyl-1H-pyrazol-3-yl]-3,5-dimethoxy-phenol 
• 41988-26-5 7-(2-bromoethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-61-5 5-hydroxy-2-phenyl-7-(2-(piperazin-1-yl)ethoxy)-4H-chromen-4-one 
• 1190373-62-6 7-(2-(diethylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-63-7 7-(2-(propylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-64-8 7-(2-(dipropylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-65-9 5-hydroxy-7-(2-(4-methylpiperazin-1-yl)ethoxy)-2-phenyl-4H-chromen-4-one 
• 1190373-66-0 7-(2-(dibutylamino)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 
• 1190373-67-1 5-hydroxy-2-phenyl-7-(2-(pyrrolidin-1-yl)ethoxy)-4H-chromen-4-one 

Relevant articles and documents

Novel synthesised flavone derivatives provide significant insight into the structural features required for enhanced anti-proliferative activity

With many cancers showing resistance to current chemotherapies, the search for novel anti-cancer agents is attracting considerable attention. Natural flavonoids have been identified as useful leads in such programmes. However, since an in-depth understanding of the structural requirements for optimum activity is generally lacking, further research is required before the full potential of flavonoids as anti-proliferative agents can be realised. Herein a broad library of 76 methoxy and hydroxy flavones, and their 4-thio analogues, was constructed and their structure-activity relationships for anti-proliferative activity against the breast cancer cell lines MCF-7 (ER +ve), MCF-7/DX (ER +ve, anthracycline resistant) and MDA-MB-231 (ER -ve) were probed. Within this library, 42 compounds were novel, and all compounds were afforded in good yields and >95% purity. The most promising lead compounds, specifically the novel hydroxy 4-thioflavones 15f and 16f, were further evaluated for their anti-proliferative activities against a broader range of cancer cell lines by the National Cancer Institute (NCI), USA and displayed significant growth inhibition profiles (e.g. compound-15f: MCF-7 (GI50 = 0.18 μM), T-47D (GI50 = 0.03 μM) and MDA-MB-468 (GI50 = 0.47 μM) and compound-16f: MCF-7 (GI50 = 1.46 μM), T-47D (GI50 = 1.27 μM) and MDA-MB-231 (GI50 = 1.81 μM)). Overall, 15f and 16f exhibited 7-46 fold greater anti-proliferative potency than the natural flavone chrysin (2d). A systematic structure-activity relationship study against the breast cancer cell lines highlighted that free hydroxyl groups and the B-ring phenyl groups were essential for enhanced anti-proliferative activities. Substitution of the 4-CO functionality with a 4-CS functionality, and incorporation of electron withdrawing groups at C-4′ of the B-ring phenyl, also enhanced activity. Molecular docking and mechanistic studies suggest that the anti-proliferative effects of flavones 15f and 16f are mediated via ER-independent cleavage of PARP and downregulation of GSK-3β for MCF-7 and MCF-7/DX cell lines. For the MDA-MB-231 cell line, restoration of the wild-type p53 DNA binding activity of mutant p53 tumour suppressor gene was indicated.

Synthesis and cytotoxicity of novel chrysin derivatives

A series of chrysin derivatives 8a-8v were prepared and tested in vitro against HCT-116 (human colon cancer cell line), Hela (human cervical carcinoma cell line), DU-145 (human prostate cell line), K562 (human leukemia cell line), and SGC-7901 (human gastric cancer cell line). The chemical structures of these compounds were confirmed by means of MS, IR, 1H NMR, 13C NMR, and elemental analysis. Among these derivatives, 7-(2-(piperazin-1- yl)ethoxy)-5-hydroxy-2-phenyl-4H-chromen-4-one, 8n, had the strongest activity against HCT-116, Hela, DU-145, K562, and SGC-7901 cells. Springer Science+Business Media, LLC 2010.

Structural Studies on Bio-active Compounds. Part 12. Tautomerism and Conformation of Aryl-substituted 1-(2-Hydroxyphenyl)-3-phenylpropane-1,3-diones in the Solid Phase and in Solution

The tautomerism of a series of aryl-substituted 1-(2-hydroxyphenyl)-3-phenylpropane-1,3-diones has been studied in deuteriochloroform solution by 1H n.m.r. techniques and, in the case of 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione and 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione, in the solid state by X-ray crystallography.Of these compounds, most exist between 80 and 95percent in the enolised form in solution and 1-(2-hydroxy-4-methoxyphenyl)-3-phenylpropane-1,3-dione adopts this tautomer in the crystal.However, 1-(2-hydroxy-4,6-dimethoxyphenyl)-3-phenylpropane-1,3-dione is present as the diketone in the solid phase and enolises very slowly in solution. 1-(6-Benzoyloxy-2-hydroxyphenyl)-3-hydroxy-3-phenylprop-2-en-1-one is shown by 1H n.m.r. spectroscopy possibly to adopt a 'coiled' conformation in solution in deuteriochloroform.