1621-56-3

Usage

Uses

Used in Anticancer Applications:
7-Methoxyisoflavone is used as an anticancer agent for its ability to inhibit the clonogenicity of human colon cancer cells. This property suggests its potential in limiting the growth and proliferation of cancerous cells, particularly in colorectal cancer.
Additionally, 7-Methoxyisoflavone is used as an activator of adenosine monophosphate-activated protein kinase (AMPK). AMPK is a key regulator of cellular energy homeostasis and has been implicated in various cellular processes, including cell growth, proliferation, and apoptosis. Activation of AMPK by 7-Methoxyisoflavone may contribute to its anticancer effects by modulating these cellular processes.
Used in Pharmaceutical Industry:
7-Methoxyisoflavone is used as a pharmaceutical candidate due to its potential therapeutic applications in cancer treatment. Its ability to target cancer cells and modulate cellular processes makes it a valuable compound for the development of novel cancer therapies.

InChI:InChI=1/C16H12O3/c1-18-12-7-8-13-15(9-12)19-10-14(16(13)17)11-5-3-2-4-6-11/h2-10H,1H3

Upstream product

• 5128-69-8 7-methoxyisoflavanone 
• 546-67-8 lead(IV) tetraacetate 
• 64-19-7 acetic acid 
• 21785-09-1 7-methoxyflavanone 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 77287-34-4 formamide 
• 186581-53-3 diazomethane 
• 13057-72-2 7-hydroxyisoflavone 
• 68-12-2 N,N-dimethyl-formamide 
• 109442-55-9 2-Hydroxy-4'-methoxy-benzoin 
• 109-94-4 formic acid ethyl ester 
• 52923-29-2 1-(2-hydroxy-4-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 122-51-0 orthoformic acid triethyl ester 
• 73220-41-4 3-bromo-7-methoxy-4H-chromen-4-one 

Downstream Products

• 76856-80-9 1-(2-hydroxy-4-methoxyphenyl)-2-phenylpropan-1-one 
• 1233943-87-7 1-[4-(2-hydroxy-4-methoxyphenyl)-5-phenylpyrimidin-2-yl]thiourea 
• 1391033-45-6 C₁₆H₁₂O₄ 
• 1427272-63-6 3-cyano-6-(2-hydroxy-4-methoxyphenyl)-5-phenylpyridine-2-(1H)-thione 
• 76182-75-7 7-methoxyisoflavone epoxide 
• 75989-82-1 6-chloro-7-methoxyisoflavone 
• 67363-58-0 5-methoxy-2-(4-phenyl-isoxazol-5-yl)-phenol 
• 105258-25-1 5-Methoxy-2-(5-phenyl-pyrimidin-4-yl)-phenol 
• 105258-11-5 2-(2-Amino-5-phenyl-pyrimidin-4-yl)-5-methoxy-phenol 
• 18439-96-8 1-(2-hydroxy-4-methoxyphenyl)-2-phenylethanone 
• 1606136-76-8 2-methyl-6-phenyl-7-(2-hydroxyl-4-methoxyphenyl)pyrazolo[1,5-a]pyrimidine 
• 1456626-68-8 3-cyano-6-(2-hydroxy-4-methoxyphenyl)-5-phenylpyridin-2(1H)-one 

Relevant academic research and scientific papers

Two-Step Laser Excitation Fluoresence Study of the Ground-and Excited-State Proton Transfer in Alcohol Solutions of 7-Hydroxyisoflavone

The intermolecular excited-state proton transfer and relaxation processes to the parent molecule were investigated for the alcohol solutions of 7-hydroxyisoflavone (7-HIF) by means of nanosecond and two-step laser excitation (TSLE) fluorescence spectrosco

Stille coupling for the synthesis of isoflavones by a reusable palladium catalyst in water

Isoflavones were synthesized from the reaction of 3-bromochromone derivatives and aryltributylstannanes via Stille coupling catalyzed by a water-soluble and reusable PdCl2(NH3)2/2,2′-cationic bipyridyl system in aqueous solution. For prototype 3-bromochromone, the coupling reaction was performed at 80°C for 24 hr with 2.5 mol% catalyst in water in the presence of tetrabutylammonium fluoride. After the reaction, the aqueous solution could be reused for several runs, indicating that its activity was only slightly decreased. For substituted 3-bromochromones, the addition of NaHCO3 and a higher reaction temperature (120°C) were required to gain satisfactory outcomes. In addition, naturally occurring products, such as daidzein, could be obtained by this protocol via a one-pot reaction.

Design, synthesis and the structure-activity relationship of agonists targeting on the ALDH2 catalytic tunnel

ALDH2, a key enzyme in the alcohol metabolism process, detoxifies several kinds of toxic small molecular aldehydes, which induce severe organ damages. The development of novel Alda-1 type ALDH2 activators was mostly relied on HTS but not rational design so far. To clarify the structure–activity relationship (SAR) of the skeleton of Alda-1 analogs by synthesis of the least number of analogs, we prepared 31 Alda-1 analogs and 3 isoflavone derivatives and evaluated for their ALDH2-activating activity. Among these, the ALDH2-activating activity of mono-halogen-substituted (Cl and Br) N-piperonylbenzamides 3b and 3 k, and non-aromatic amides 8a-8c, were 1.5–2.1 folds higher than that of Alda-1 at 20 μM. The relationship between binding affinity in computer aided molecular docking model and the ALDH2-activating activity assays were clarified as follows: for Alda-1 analogs, with the formation of halogen bonds, the enzyme-activating activity was found to follow a specific regression curve within the range between ?5 kcal/mol and ?4 kcal/mol. For isoflavone derivatives, the basic moiety on the B ring enhance the activating activity. These results provide a new direction of utilizing computer-aided modeling to design novel ALDH2 agonists in the future.

Transient and Recyclable Halogenation Coupling (TRHC) for Isoflavonoid Synthesis with Site-Selective Arylation

A transient and recyclable C?H iodination has been designed for the synthesis of isoflavonoids through the domino reactions of o-hydroxyphenyl enaminones and aryl boronic acids in the presence of catalytic KI and Pd catalyst. Instead of the conventional cross-coupling strategy employing pre-halogenated substrates, this method transforms raw C?H bond by means of a transient C?H halogenation to smoothly relay the subsequent C-arylation. Consequently, such a method avoids the pre-functionalization for C?halogen bond installation as well as the generation of stoichiometric halogen-containing waste following the cross-coupled product, disclosing an intriguing new coupling protocol to forge the C?C bond in the virgin area between classical C?X (X=halogen) bond cross coupling and the C?H activation.

Development of a general approach to the synthesis of a library of isoflavonoid derivatives

Isoflavonoids are a class of organic compounds that act primarily as antioxidants. They are produced almost exclusively by various members of the bean family including soybeans, tofu, peanuts, chick peas, and alfalfa. The antioxidant characteristics that isoflavonoids exhibit help hinder the progression of certain cancers, primarily breast, prostate, and colon cancer. We have developed a three-five step synthesis for obtaining a suite of isoflavonoid derivatives. The synthesis involves an enamine formation, a ring closure and halogenation, a Suzuki coupling, and finally a global deprotection to obtain the respective isoflavonoid derivatives.

Novel synthesis of 3-phenyl-chromen-4-ones using n-heterocyclic carbene as organocatalyst: An efficient domino catalysis type approach

Herein is reported a simple and efficient synthesis of isoflavones starting from various substituted phenacyl bromides and salicylaldehydes in presence of NHC. The mechanism involved domino catalysis type approach with consumption and regeneration of catalyst in two catalytic cycles. This method proved to be very lucrative and gives very good yield. The method described here represents an environmentally benign alternative to classical approach.

Synthesis of isoflavones via base catalysed condensation reaction of deoxybenzoin

Base catalysed condensation reaction of o-hydroxyl-α- phenylacetophenones with formyl reagents affords various substituted isoflavones. Many bases were tested in the condensation reaction and DMAP was found to be the most effective catalysis.

COMPOUNDS FOR IMMUNOPOTENTIATION

Methods of stimulating an immune response and treating patients responsive thereto with 3,4-di(1H-indol-3-yl)-1H-pyrrole-2,5-diones, staurosporine analogs, derivatized pyridazines, chromen-4-ones, indolinones, quinazolines, nucleoside analogs, and other small molecules are disclosed.

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.