92152-60-8

Usage

Preparation

Preparation by reaction of p-bromophenylacetonitrile with resorcinol, ? in the presence of boron trifluoride etherate under hydrogen chloride atmosphere (8–10 h) and at r.t. overnight (90%) ; ? in the presence of zinc chloride and hydrogen chloride (Hoesch reaction).

InChI:InChI=1/C14H11BrO3/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

• 16532-79-9 4-Bromophenylacetonitrile 
• 108-46-3 recorcinol 
• 1878-68-8 2-(4-bromophenyl)-acetic acid 

Downstream Products

• 1241384-54-2 2-(4-bromophenyl)-1-(2-hydroxy-4-(2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethoxy)phenyl)ethanone 
• 320741-23-9 C₁₄H₁₂BrNO₃ 
• 1239488-79-9 C₂₀H₁₅BrClNO₂ 
• 1415465-13-2 3-(4-bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde 
• 1324010-51-6 4-(2-(2,4-dihydroxyphenyl)-2-oxoethyl)benzonitrile 
• 121060-07-9 Acetic acid (2S,3R,4S,5R,6R)-4,5-diacetoxy-6-acetoxymethyl-2-{4-[2-(4-bromo-phenyl)-acetyl]-3-hydroxy-phenoxy}-tetrahydro-pyran-3-yl ester 
• 96644-12-1 2-trifluoromethyl-7-hydroxy-4'-bromoisoflavone 
• 96644-14-3 ethyl 3-(4-bromophenyl)-7-hydroxy-4-oxo-4H-chromene-2-carboxylate 
• 96644-05-2 7-hydroxy-3-(4’-bromophenyl)-4H-1-benzopyran-4-one 
• 121076-26-4 Acetic acid (2R,3R,4S,5R,6S)-3,5-diacetoxy-2-acetoxymethyl-6-[3-(4-bromo-phenyl)-4-oxo-4H-chromen-7-yloxy]-tetrahydro-pyran-4-yl ester 

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

Synthesis of structurally diverse biflavonoids

Synthetic biflavonoids are associated with interesting biological activities, yet they remain poorly explored within drug discovery. Recent years have witnessed a growing interest in synthetic approaches that can provide access to structurally novel biflavonoids so that the biological usefulness of this compound class can be more fully investigated. Herein, we report upon the exploration of strategies based around Suzuki-Miyaura cross-coupling and alcohol methylenation for the synthesis of two classes of biflavonoids: (i) rare ‘hybrid’ derivatives containing flavonoid monomers belonging to different subclasses, and (ii) homodimeric compounds in which the two flavonoid monomers are linked by a methylenedioxy group. Application of these strategies enabled the preparation of a structurally diverse collection of novel biflavonoids from readily-available starting materials, thereby facilitating the probing of uncharted regions of biologically interesting chemical space.

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

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.

NOVEL S-NITROSOGLUTATHIONE REDUCTASE INHIBITORS

The present invention is directed to inhibitors of S-nitrosoglutathione reductase (GSNOR), pharmaceutical compositions comprising such GSNOR inhibitors, and methods of making and using the same.

Synthesis and structural study on heterocyclic compounds 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones: Crystal structure of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one

Six new isoflavone-based esters, 7-decanoyloxy-3-(4′-substitutedphenyl)-4H-1-benzopyran-4-ones, derived from 1,3-benzenediol (resorcinol) and different para substituted phenylacetic acids have been synthesized and characterized. The molecular structures of the title compounds were elucidated with the employment of physical measurements and spectroscopic techniques (FTIR, 1D and 2D NMR). The conformation of 7-decanoyloxy-3-(4′-methylphenyl)-4H-1-benzopyran-4-one was determined by single crystal X-ray diffraction analysis of which the title compound crystallized into triclinic lattice with P-1 space group. Crystal structure of the title compound also revealed that the two phenyl rings of the central moiety were planar whilst the heterocyclic ring was found to pucker slightly from the mean plane.

Design, synthesis, and immunosuppressive activity of new deoxybenzoin derivatives

In the search for potential immunosuppressive agents with high efficacy and low toxicity, a series of new deoxybenzoins were synthesized and evaluated for their cytotoxicity and immunosuppressive activity. Among the synthesized compounds, four deoxybenzoi

COMPOUNDS USEFUL FOR THE INHIBITION OF ALDH

The present invention provides novel antidipsotropic compounds. The invention further provides methods of inhibiting ALDH-2 using the compounds described herein. Methods for modulating alcohol consumption, alcohol dependence and/or alcohol abuse by administering the compounds of the invention to an individual are also provided. The present invention further provides a rationale for designing additional novel antidipsotropic compounds.

Synthesis of daidzin analogues as potential agents for alcohol abuse

Daidzin, the active principle of an herbal remedy for 'alcohol addiction', has been shown to reduce alcohol consumption in all laboratory animals tested to date. Correlation studies using structural analogues of daidzin suggests that it acts by raising the monoamine oxidase (MAO)/mitochondrial aldehyde dehydrogenase (ALDH-2) activity ratio (J. Med. Chem. 2000, 43, 4169). Structure-activity relationship (SAR) studies on the 7-O-substituted analogues of daidzin have revealed structural features important for ALDH-2 and MAO inhibition (J. Med. Chem. 2001, 44, 3320). We here evaluated effects of substitutions at 2, 5, 6, 8, 3′ and 4′ positions of daidzin on its potencies for ALDH-2 and MAO inhibition. Results show that analogues with 4′-substituents that are small, polar and with hydrogen bonding capacities are most potent ALDH-2 inhibitors, whereas those that are non-polar and with electron withdrawing capacities are potent MAO inhibitors. Analogues with a 5-OH group are less potent ALDH-2 inhibitors but are more potent MAO inhibitors. All the 2-, 6-, 8- and 3′-substituted analogues tested so far do not inhibit ALDH-2 and/or have decreased potencies for MAO inhibition. This, together with the results obtained from previous studies, suggests that a potent antidipsotropic analogue would be a 4′,7-disubstituted isoflavone. The 4′-substituent should be small, polar, and with hydrogen bonding capacities such as, -OH and -NH2; whereas the 7-substituent should be a straight-chain alkyl with a terminal polar function such as -(CH 2)n-OH with 2≤n ≤6, -(CH2) n-COOH with 5≤n ≤10, or -(CH2)n-NH 2 with n ≥4.

EFFECTIVE SYNTHESIS OF 7-HYDROXYISOFLAVONE O-GLUCOSIDES

An effective procedure for condensing acetobromoglucose with 2,4-dihydroxy phenyl benzyl ketones has been developed.The 2-hydroxy-4-(β-D-tetra-O-acetylglucopyranosyloxy)phenyl benzyl ketones synthesized with yields of 47-69percent have been converted under the action of ethyl orthoformate in pyridine solution into 7-hydroxyisoflavone O-glukosides and these have also been obtained by the glycosylation of 7-hydroxyisoflavone.The advantages and disadvantages of the alternative pathways of the synthesis of 7-hydroxyisoflavone O-glykosides are discussed.