96644-05-2

Usage

Uses

Used in Pharmaceutical Industry:
AKOS BBS-00006060 is used as a reactant for the synthesis of isoflavone derivatives and analogs, which have potential applications in the development of pharmaceuticals and nutraceuticals for various health benefits.
Used in Synthesis of Isoflavone Derivatives:
AKOS BBS-00006060 is used as a key intermediate in the synthesis of isoflavone derivatives, which are known for their diverse biological activities, including antioxidant, anti-inflammatory, and estrogenic properties.
Used in Synthesis of Isoflavone Analogs:
AKOS BBS-00006060 is also used in the synthesis of isoflavone analogs, which can be further modified to enhance their biological activities or to develop new drugs with improved pharmacological properties.

InChI:InChI=1/C15H9BrO3/c16-10-3-1-9(2-4-10)13-8-19-14-7-11(17)5-6-12(14)15(13)18/h1-8,17H

Upstream product

• 1878-68-8 2-(4-bromophenyl)-acetic acid 
• 16532-79-9 4-Bromophenylacetonitrile 
• 108-46-3 recorcinol 
• 92152-60-8 2-(4-bromophenyl)-1-(2,4-dihydroxyphenyl)ethan-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 124-63-0 methanesulfonyl chloride 
• 122-51-0 orthoformic acid triethyl ester 

Downstream Products

• 1160861-91-5 7-decanoyloxy-3-(4'-bromophenyl)-4H-1-benzopyran-4-one 
• 1415465-13-2 3-(4-bromophenyl)-7-hydroxy-4-oxo-4H-1-benzopyran-8-carboxaldehyde 

Relevant academic research and scientific papers

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

New para-substituted non-symmetric isoflavones for their fast photo-switching ability: Synthesis and their liquid crystal characterization

The first example of non-symmetric isoflavone-based fast photo-switchable liquid crystals with different functional groups at the terminal position were synthesized and characterized. Polarizing optical microscopy study revealed that the compounds showed least ordered nematic phase. Optical photo switching study exhibited very fast photoisomerization effect in solution. The E-Z and Z-E conversion occurred around 3-5 s and 40-700 s respectively. This is also the first example of para-substituted non-symmetric isoflavone liquid crystals exhibiting very fast photo switching property in solution. Argument based on non-symmetrical behaviour might be the reason for the observed behaviour.

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.

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.

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.

Mixed Anhydride of Acetic and Formic Acids in the Synthesis of Chromones. 2. Synthesis of 3-Arylchromones

A study was carried out on the reaction of α-substituted 2-hydroxyacetophenones eith the mixed anhydride of acetic and formic acids in the presence of bases of different strength.Chromones containing a conjugated electron-withdrawing substituent at C(3) are formed in close to quantitative yield in the presence of triethylamine.The preparation of chromones containing an unconjugated substituent under these conditions is recommended only for 5-hydroxychromones.

CHEMISTRY OF ISOFLAVONE HETEROCYCLIC ANALOGS. 10. SYNTHESIS OF PYRIMIDINES BY RECYCLIZATION OF ISOFLAVONES AND THEIR HETEROCYCLIC ANALOGS

Isoflavones and their thiazole and pyrazole analogs are recyclized into the corresponding 4-(2-hydroxyphenyl)-pyrimidine derivatives under the effect of amidines.Their PMR spectra were studied.The effects related to the formation and strength of the intra

SYNTHESIS OF ANALOGS OF NATURAL ISOFLAVONES FROM 2,4-DIHYDROXYDEOXYBENZOINS

A number of analogs of natural isoflavones have been synthesized.The starting materials were 2,4-dihydroxydeoxybenzoins obtained under modified conditions of the Houben-Hoesch reaction.The yields of the isoflavones synthesized were 63-69percent.All the an