15485-70-8

Basic information

• Product Name: 2-(4-Fluorophenyl)-1-(2,4-dihydroxyphenyl)ethanone
• Synonyms: 1-(2,4-dihydroxyphenyl)-2-(4-fluorophenyl)ethanone(SALTDATA: FREE);1-(2,4-dihydroxyphenyl)-2-(4-fluorophenyl)ethanone
• CAS NO: 15485-70-8
• Molecular Formula: C₁₄H₁₁FO₃
• Molecular Weight: 246.23
• Mol File: 15485-70-8.mol
• Article Data: 20

Chemical Properties

• Melting Point: 144–145°C
• Boiling Point: 434.1°C at 760 mmHg
• Flash Point: 216.3°C
• Appearance: /
• Density: 1.347g/cm³
• Vapor Pressure: 3.84E-08mmHg at 25°C
• Refractive Index: 1.624
• CAS DataBase Reference: 2-(4-Fluorophenyl)-1-(2,4-dihydroxyphenyl)ethanone(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(4-Fluorophenyl)-1-(2,4-dihydroxyphenyl)ethanone(15485-70-8)
• EPA Substance Registry System: 2-(4-Fluorophenyl)-1-(2,4-dihydroxyphenyl)ethanone(15485-70-8)

Safety Data

• Hazardous Substances Data: 15485-70-8(Hazardous Substances Data)

Usage

Preparation

Preparation by reaction of p-fluorophenylacetonitrile with resorcinol (Hoesch reaction).

InChI:InChI=1/C14H11FO3/c15-10-3-1-9(2-4-10)7-13(17)12-6-5-11(16)8-14(12)18/h1-6,8,16,18H,7H2

Upstream product

• 108-46-3 recorcinol 
• 405-50-5 p-Fluorophenylacetic acid 
• 459-22-3 4-fluorophenylacetonitrile 

Downstream Products

• 128040-47-1 2-(4-fluorophenyl)-1-(2-hydroxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone 
• 240410-83-7 3-(4-fluorophenyl)-7-hydroxy-2-methyl-4H-chromen-4-one 
• 315233-72-8 3-(4-fluorophenyl)-7-hydroxy-2-(trifluoromethyl)-4H-chromen-4-one 
• 131814-59-0 2-[3-(4-Fluoro-phenyl)-4-oxo-4H-chromen-7-yloxy]-propionic acid methyl ester 
• 131814-58-9 3-(4-Fluoro-phenyl)-7-isopropoxy-chromen-4-one 
• 121060-10-4 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(4-fluoro-phenyl)-4-oxo-4H-chromen-7-yloxy]-tetrahydro-pyran-4-yl ester 
• 121060-05-7 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[2-(4-fluoro-phenyl)-acetyl]-3-hydroxy-phenoxy}-tetrahydro-pyran-3-yl ester 
• 128040-46-0 1-(2-hydroxy-4-methoxyphenyl)-2-(4-fluorophenyl)-1-ethanone 
• 15584-10-8 7-hydroxy-3-(4'-fluorophenyl)-4H-1-benzopyran-4-one 
• 374702-69-9 3-(4-fluorophenyl)-7-hydroxy-4-oxo-4H-chromene-2-carboxylic acid 
• 15732-44-2 ethyl 3-(4-fluorophenyl)-7-hydroxy-4-oxo-4H-chromene-2-carboxylate 

Relevant articles and documents

A Concise Approach to Oxo-Dehydrorotenoid by Direct Lactonization and the Total Syntheses of Stemonone, Rotenonone, 6-Oxo-dehydroelliptone, and 6-Oxo-6a,12a-dehydrodeguelin

An approach to construct the oxo-dehydrorotenoids via direct lactonization of isoflavone-2-carboxylic acids is reported. The present reaction proceeds smoothly with good substrate scope and an operationally simple protocol. The application of this method

Novel isoflavone derivative, preparation method therefor and medicinal use of novel isoflavone derivative

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Novel SERMs based on 3-aryl-4-aryloxy-2H-chromen-2-one skeleton - A possible way to dual ERα/VEGFR-2 ligands for treatment of breast cancer

There is considerable interest in developing new SERMs as multifunctional agents in women's health. Development of dual selective estrogen receptor modulators/VEGFR-2 inhibitors (SERMs/V-2I) has been an attractive strategy for the discovery of new breast cancer therapeutic agents. Our previous efforts led to the preparation of a series of 3-aryl-4-anilino-2H-chromen-2-ones endowed with potent estrogen receptor binding affinity and anti-proliferative efficacy. In this study, various structurally related 3-aryl-4-anilino/aryloxy-2H-chromen-2-one analogues were rationally designed, synthesized and evaluated as a new chemo-type of dual ERα and VEGFR-2 inhibitors. Most of the derivatives exhibited potent activities in both enzymatic and cellular assays. SAR investigation revealed that introducing of bioisosteric O atom at the C-4 position of coumarin scaffold is beneficial to improve the inhibitory potency, especially in ERα binding affinity assay. Furthermore, most of the piperidyl substituted compounds showed better inhibitory activity against MCF-7 and Ishikawa cells than lead compounds BL-18d, tamoxifen and Vandetanib. Optimization of the hit compound, identified in an ERα binding affinity assay, led to compound 42d, exhibiting an IC50 for ERα binding affinity of 2.19 μM while retaining an excellent inhibition on VGFR-2 as well as a potent suppression on the growth of angiogenesis-related cells. In RT-PCR assay, 42d exerted significantly antiestrogenic property via suppressing the expression of progesterone receptor (PgR) mRNA in MCF-7 cells, which was consistent with the ERα antagonistic property of a selective estrogen receptor modulator. Further mechanism investigation demonstrated that compound 42d could inhibit the activation of VEGFR-2 and subsequent signaling transduction of Raf-1/MAPK/ERK pathway in MCF-7 cells. All these results together with molecular modeling studies open a new avenue for the development of multifunctional agents targeting ERα and VEGFR-2 in the therapy of some breast cancers.