24160-14-3

Usage

Uses

Used in Pharmaceutical Industry:
3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE is used as a modulator for adenosine monophosphate-activated protein kinase (AMPK) for its potential role in regulating cellular energy balance and metabolism. AMPK is a key enzyme in cellular energy homeostasis, and its activation has been linked to various beneficial effects, including improved glucose and lipid metabolism, as well as potential anti-cancer and anti-inflammatory properties.
Used in Anticancer Applications:
3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE may be employed as an anticancer agent due to its ability to modulate AMPK, which can lead to the inhibition of tumor growth and progression. By targeting this important cellular pathway, the compound may offer a novel therapeutic approach for the treatment of various types of cancer.
Used in Metabolic Disorders:
Given its role in modulating AMPK, 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE may also be used in the treatment of metabolic disorders such as diabetes and obesity. Activation of AMPK can improve insulin sensitivity and promote fatty acid oxidation, which may help in managing these conditions.
Used in Drug Delivery Systems:
Similar to gallotannin, 3',4'-DIMETHOXY-7-HYDROXYISOFLAVONE could potentially be incorporated into drug delivery systems to enhance its bioavailability and therapeutic efficacy. By using various carriers such as organic or metallic nanoparticles, the compound's delivery to target cells and tissues can be improved, leading to better treatment outcomes.

InChI:InChI=1/C17H14O5/c1-20-14-6-3-10(7-16(14)21-2)13-9-22-15-8-11(18)4-5-12(15)17(13)19/h3-9,18H,1-2H3

Upstream product

• 111090-19-8 3-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-7-yl acetate 
• 24126-98-5 1-(2,4-dihydroxyphenyl)-2-(3,4-dimethoxyphenyl)ethan-1-one 
• 68-12-2 N,N-dimethyl-formamide 
• 93-40-3 (3,4-Dimethoxyphenyl)acetic acid 
• 124-63-0 methanesulfonyl chloride 
• 108-46-3 recorcinol 
• 3557-22-0 1-(2-hydroxy-5-((tetrahydro-2H-pyran-2-yl)oxy)phenyl)ethan-1-one 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 59887-89-7 7-hydroxy-4H-chromen-4-one 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 935659-66-8 3-(3,4-dimethoxyphenyl)-7-(tetrahydro-2H-pyran-2-yloxy)-4H-chromen-4-one 

Downstream Products

• 111090-19-8 3-(3,4-dimethoxyphenyl)-4-oxo-4H-chromen-7-yl acetate 
• 1621-61-0 cabreuvin 
• 485-63-2 3',4',7-trihydroxyisoflavone 
• 951969-45-2 3-(3,4-dimethoxyphenyl)-9-(3-morpholin-4-ylpropyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929828-69-3 3-(3,4-dimethoxyphenyl)-9-(thien-2-ylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929493-85-6 3-(3,4-dimethoxyphenyl)-9-(2-thien-2-ylethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929402-69-7 3-(3,4-dimethoxyphenyl)-9-(2-furylmethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 929444-74-6 3-(3,4-dimethoxyphenyl)-9-(3-phenylpropyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 951954-75-9 3-(3,4-dimethoxyphenyl)-9-(2-methoxyethyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 951959-02-7 9-(3-methoxypropyl)-3-(3,4-dimethoxyphenyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]oxazin-4-one 
• 1268612-94-7 7-(2-diethylamino-ethoxy)-3-(3,4-dimethoxyphenyl)-4H-chromen-4-one 
• 921112-72-3 3-(3,4-dimethoxyphenyl)-7-(2-piperidin-1-yl-ethoxy)-4H-chromen-4-one 
• 1268612-93-6 3-(3,4-dimethoxyphenyl)-7-(2-pyrrolidin-1-yl-ethoxy)-4H-chromen-4-one 
• 921136-07-4 3-(3,4-dimethoxy-phenyl)-7-(2-morpholin-1-yl-ethoxy)-4H-chromen-4-one 

Relevant academic research and scientific papers

Identification of ortho catechol-containing isoflavone as a privileged scaffold that directly prevents the aggregation of both amyloid β plaques and tau-mediated neurofibrillary tangles and its in vivo evaluation

In this study, polyhydroxyisoflavones that directly prevent the aggregation of both amyloid β (Aβ) and tau were expediently synthesized via divergent Pd(0)-catalyzed Suzuki-Miyaura coupling and then biologically evaluated. By preliminary structure–activity relationship studies using thioflavin T (ThT) assays, an ortho-catechol containing isoflavone scaffold was proven to be crucial for preventing both Aβ aggregation and tau-mediated neurofibrillary tangle formation. Additional TEM experiment confirmed that ortho-catechol containing isoflavone 4d significantly prevented the aggregation of both Aβ and tau. To investigate the mode of action (MOA) of 4d, which possesses an ortho-catechol moiety, 1H-15N HSQC NMR analysis was thoroughly performed and the result indicated that 4d could directly inhibit both the formation of Aβ42 fibrils and the formation of tau-derived neurofibrils, probably through the catechol-mediated nucleation of tau. Finally, 4d was demonstrated to alleviate cognitive impairment and pathologies related to Alzheimer's disease in a 5XFAD transgenic mouse model.

Electrochemical Generation of Hypervalent Bromine(III) Compounds

In sharp contrast to hypervalent iodine(III) compounds, the isoelectronic bromine(III) counterparts have been little studied to date. This knowledge gap is mainly attributed to the difficult-to-control reactivity of λ3-bromanes as well as to their challenging preparation from the highly toxic and corrosive BrF3 precursor. In this context, we present a straightforward and scalable approach to chelation-stabilized λ3-bromanes by anodic oxidation of parent aryl bromides possessing two coordinating hexafluoro-2-hydroxypropanyl substituents. A series of para-substituted λ3-bromanes with remarkably high redox potentials spanning a range from 1.86 V to 2.60 V vs. Ag/AgNO3 was synthesized by the electrochemical method. We demonstrate that the intrinsic reactivity of the bench-stable bromine(III) species can be unlocked by addition of a Lewis or a Br?nsted acid. The synthetic utility of the λ3-bromane activation is exemplified by oxidative C?C, C?N, and C?O bond forming reactions.

Synthesis, antimycobacterial evaluation and pharmacophore modeling of analogues of the natural product formononetin

Abstract The synthesis and antimycobacterial activity of formononetin analogues is hereby reported. Formononetin and its analogue 11E showed 88% and 95% growth inhibition, respectively, against the H37Rv strain of Mycobacterium tuberculosis. Pharmacophore modeling studies indicated that the presence of a hydroxyl group in formononetin and its analogues, is crucial for maintaining activity.

Synthesis and tautomerization of hydroxylated isoflavones bearing heterocyclic hemi-aminals

The aminomethylation of hydroxylated isoflavones with 2-aminoethanol, 3-amino-1-propanol, 4-amino-1-butanol, and 5-amino-1-pentanol in the presence of excess formaldehyde led principally to 9-(2-hydroalkyl)-9,10-dihydro-4H,8H-chromeno[8,7-e][1,3]-oxazin-4-ones 4 and/or the tautomeric 7-hydroxy-8-(1,3-oxazepan-3-ylmethyl)-4H-chromen-4-ones 5. The ratio of these tautomers was dependent on solvent polarity, electronic effects of aryl substituents in the isoflavone and the structure of the amino alcohol. NMR studies confirmed the interconversion of tautomeric forms.

Oxidative dimerisation of isoflavones: Synthesis of kudzuisoflavone a and related compounds

Kudzuisoflavone-A was successfully synthesised via oxidative dimerisation of daidzein in the presence of cuprous chloride. Appropriately substituted isoflavones also undergo regioselective oxidative dimerisation when treated with thallium trifluoroacetate to give novel 6′,6′″-biisoflavones in good yield. A rationale for the regioselectivity is proposed.

Synthetic analogs of daidzein, having more potent osteoblast stimulating effect

A series of didzein derivatives were synthesized and assessed for stimulation of osteoblast differentiation using primary cultures of rat calvarial osteoblasts. Data suggested that three synthetic analogs, 1c, 3a and 3c were several folds more potent than daidzein in stimulating differentiation and mineralization of osteoblasts. Further, these three compounds did not show any estrogen agonistic activity, however had mild estrogen antagonistic effect. Out of the three compounds, 3c was found to maximally increase the mineralization of bone marrow osteoprogenitor cells. Compound 3c also robustly increased the mRNA levels of osteogenic genes including bone morphogenetic protein-2 and osteocalcin in osteoblasts. Unlike daidzein, 3c did not inhibit osteoclastogenesis. Collectively, we demonstrate osteogenic activity of daidzein analogs at significantly lower concentrations than daidzein.

Synthesis of various kinds of isoflavones, isoflavanes, and biphenyl- ketones and their 1,1-diphenyl-2-picrylhydrazyl radical-scavenging activities

Forty-eight kinds of isoflavones (8), thirty-one isoflavanes (9), and forty-seven biphenyl-ketones (10, 10') were synthesized from eleven kinds of substituted phenols (11) and six phenylacetic acids (12). Among them, seventy-five compounds are new. The radical scavenging activities of these compounds were evaluated using 1,1- diphenyl-2-picrylhydrazyl (DPPH) at pH 6.0. We found that thirty-nine out of forty-three compounds having a catechol moiety on either the A- or the B-ring exhibited a high activity (ED50=12-54 μM) similar to that of catechin. In these cases, the remaining part of their structure seemed to have little effect on their activity. Many 6- or 8-hydroxyisoflavanes (9E-I) and their biphenyl-ketone derivatives (10E-H) also showed a high activity (ED50=50=26-32 μM). This study suggests that natural isoflavones have the possibilities of exhibiting antioxidant activities through the hydroxylation at the C6-, C8-, or C3'-position or the formation of the isoflavanes (9) and/or the biphenyl-ketone derivatives (10') by metabolism or biotransformation.

FLAVONOID PPAR AGONISTS

The present invention relates to PPAR agonists, and their use in therapy including the treatment of disease. In particular, the invention relates to flavonoid compounds which are PPAR-gamma agonists and/or PPAR alpha/gamma dual agonists.

7-Hydroxy-benzopyran-4-one derivatives: A novel pharmacophore of peroxisome proliferator-activated receptor α and -γ (PPARα and γ) dual agonists

Design, synthesis, and in vitro bioevaluation of a new class of potential dual PPARα and γ agonists discovered through a structure-driven design paradigm are described. The 7-hydroxy-benzopyran-4-one moiety (includes flavones, flavanones, and isoflavones) is the key pharmacophore of these novel molecules, exhibiting similarity to the core structure of both fibrates and thiazolidinediones. New lead PPAR ligands were identified from "natraceuticals" and synthetic analogues. In total, 77 molecules, including chalcones, flavones, flavanones, isoflavones, and pyrazole derivatives, were screened and structure-activity relationship studies of the dual agonists undertaken. Compounds 68, 70, 72, and 76 were identified as novel and potent dual PPARα and γ agonists. These novel molecules may have the potential to be the future leads in PPAR-related disorders, including type II diabetes mellitus and metabolic syndrome. 2009 American Chemical Society.

ISOFLAVONOID DIMERS

Novel compounds based on phenyl-substituted naphtho[l,2-g]chrysene compounds (A) are described. The compounds are obtainable by dimerisation of 3-phenylchroman (isoflavonoid) ring systems (B). Methods of synthesis of the novel dimeric compounds, compositi