15485-70-8

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

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

Downstream Products

• 128040-47-1 2-(4-fluorophenyl)-1-(2-hydroxy-4-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethanone 
• 15584-10-8 7-hydroxy-3-(4'-fluorophenyl)-4H-1-benzopyran-4-one 
• 128040-46-0 1-(2-hydroxy-4-methoxyphenyl)-2-(4-fluorophenyl)-1-ethanone 
• 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 
• 315233-72-8 3-(4-fluorophenyl)-7-hydroxy-2-(trifluoromethyl)-4H-chromen-4-one 
• 240410-83-7 3-(4-fluorophenyl)-7-hydroxy-2-methyl-4H-chromen-4-one 
• 1224164-39-9 4-(2-(4-fluorophenyl)-1-(4-hydroxyphenylimino)ethyl)benzene-1,3-diol 
• 1224164-35-5 4-(2-(4-fluorophenyl)-1-(p-tolylimino)ethyl)benzene-1,3-diol 
• 1224164-37-7 4-(1-(4-chlorophenylimino)-2-(4-fluorophenyl)ethyl)benzene-1,3-diol 
• 1224164-38-8 4-(2-(4-fluorophenyl)-1-(4-nitrophenylimino)ethyl)benzene-1,3-diol 
• 1224164-36-6 4-(1-(4-bromophenylimino)-2-(4-fluorophenyl)ethyl)benzene-1,3-diol 
• 1241384-48-4 2-(4-fluorophenyl)-1-(2-hydroxy-4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)ethanone 
• 1396600-07-9 C₁₄H₁₃FO₂ 
• 1155265-02-3 1-(2,4-dihydroxyphenyl)-2-(4-fluorophenyl)ethanone oxime 

Relevant academic research and scientific papers

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

The invention relates to the field of pharmaceutical chemistry, relates to an isoflavone derivative, a preparation method therefor and medicinal use of the novel isoflavone derivative and particularlyrelates to isoflavone derivatives represented by a general formula (I) shown in the description, preparation methods therefor, pharmaceutical compositions containing these compounds and medicinal useof the isoflavone derivatives and the pharmaceutical compositions, particularly use of drugs for preventing or treating hyperlipidemia, type II diabetes, atherosclerosis and non-alcoholic fatty hepatitis.

Structure-guided design and synthesis of isoflavone analogs of GW4064 with potent lipid accumulation inhibitory activities

Our group has previously reported a series of isoflavone derivatives with antidyslipidemic activity. With this background, a series of isoflavone analogs of GW4064 were designed, synthesized and evaluated the lipid-lowering activity of analogs. As a result, most of compounds significantly reduced the lipid accumulation in 3T3-L1 adipocytes and four of them (10a, 11, 15c and 15d) showed stronger inhibitory than GW4064. The most potent compound 15d exhibited promising agonistic activity for FXR in a cell-based luciferase reporter assay. Meanwhile, 15d up-regulated FXR, SHP and BSEP gene expression and down-regulated the mRNA expression of lipogenesis gene SREBP-1c. Besides, an improved safety profile of 15d was also observed in a HepG2 cytotoxicity assay compared with GW4064. The obtained biological results were further confirmed by a molecular docking study showing that 15d fitted well in the binding pocket of FXR and interacted with some key residues simultaneously.

A Direct Synthesis of 2-(ω-Carboxyalkyl)isoflavones from ortho-Hydroxylated Deoxybenzoins

As part of a program focused on the development of new antineoplastic agents based on scaffolds found in natural products, we explored the isoflavone family as potential enzyme inhibitors. We required biotin-modified isoflavones to identify potential biological targets, and we selected the C-2 position in isoflavones as an attachment site for an alkyl group bearing a terminal carboxylic acid to which we could attach a biotin derivative. The base-catalyzed condensation of 2,4-dihydroxy-substituted deoxybenzoins with cyclic anhydrides mediated by a combination of triethylamine and 1,8-diazabicyclo[5.4.0]undec-7-ene led to an efficient synthesis of the desired 2-(ω-carboxyalkyl)isoflavones with functional groups at C-5, 6 and 7 and with various substituents in the C-3 phenyl group.

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.

ANTI-ESTROGENIC COMPOUNDS

The present disclosure provides a compound of Formula I: or a pharmaceutically acceptable salt wherein X, R1-R8, Y1-Y5, m, n, p, and q are defined herein. The novel 2H-chromene compounds are useful for the modul

Novel daidzein analogs and their in vitro anti-influenza activities

A series of novel isoflavonoids were synthesized based on structural modifications of daidzein, an active ingredient of traditional Chinese medicine (TCM) and evaluated for their anti-influenza activity, in vitro, against H1N1 Tamiflu-resistant (H1N1 TR) virus in the MDCK cell line. Among them, 4-oxo-4H-1-benzopyran-8-carbaldehydes 11a-11g were most promising, and they demonstrated better activities and selectivities comparable to those the reference ribarivin, a nucleoside antiviral agent. 3-(4-Bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde (11c) displayed the best inhibitory activity (EC50, 29.0 μM) and selectivity index (SI>10.3). Analysis of the structure￡activity relationships (SAR) indicated that both the non-naturally-occurring Br-substituted B-ring and appropriate CHO and OH groups on the A-ring might be critical for the activity and selectivity against H1N1 TR influenza viruses.

Development of 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs) from natural isoflavones, a new class of fluorescent scaffolds for biological imaging

Starting from 7-hydroxyisoflavones, we developed a new class of fluorescent scaffolds, 3-alkyl-6-methoxy-7-hydroxy-chromones (AMHCs, MW ～ 205.19, λab ～ 350 nm, λem ～ 450 nm) via a trial and error process. AMHCs have the advantages of being a small molecular moiety, having strong fluorescence in basic buffers, reasonable solubility and stability, non-toxicity, and are conveniently linked to pharmacophores. AMHCs were successfully used in fluorescence microscopy imaging of cells and tissues. This journal is

AZETIDINE ESTROGEN RECEPTOR MODULATORS AND USES THEREOF

Described herein are compounds that are estrogen receptor modulators. Also described are pharmaceutical compositions and medicaments that include the compounds described herein, as well as methods of using such estrogen receptor modulators, alone and in combination with other compounds, for treating diseases or conditions that are mediated or dependent upon estrogen receptors.

Design, synthesis and molecular simulation studies of dihydrostilbene derivatives as potent tyrosinase inhibitors

The synthesis, molecular modeling and biological evaluation of substituted deoxybenzoins and optimized dihydrostilbenes are reported. Preliminary structure-activity relationship data were elucidated and lead compounds suitable for further optimization wer