1247-97-8

Usage

Uses

Used in Pharmaceutical Industry:
QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is used as a potential therapeutic agent for its anti-cancer properties, where it may contribute to the inhibition of tumor growth and the modulation of various oncological signaling pathways. Its enhanced stability and bioavailability compared to the parent compound, quercetin, make it a promising candidate for further research and pharmaceutical development.
Used in Antiviral Applications:
In the field of virology, QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is used as an antiviral agent, leveraging its ability to interfere with viral replication and pathogenesis, offering a potential strategy for the treatment of viral infections.
Used in Neuroprotective Therapies:
QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER is utilized as a neuroprotective agent, given its potential to shield the nervous system from damage and degeneration, which is particularly relevant in the context of neurodegenerative diseases.
Each of these applications underscores the versatility and potential of QUERCETIN-3,5,7,3',4'-PENTAMETHYL ETHER in various medical and health-related fields, warranting continued investigation into its mechanisms of action and therapeutic potential.

Upstream product

• 186581-53-3 diazomethane 
• 117-39-5 quercetol 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 1245-15-4 retusin 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 76650-20-9 1-(2,4,6-trimethoxyphenyl)-3-(3,4-dimethoxyphenyl)propenone 
• 29080-58-8 5-hydroxy-3',4',7-trimethoxyflavone 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 832-58-6 1-(2,4,6-trimethoxyphenyl)ethanone 
• 17874-42-9 2'-hydroxy-2,4',6'-trimethoxyacetophenone 
• 1385652-00-5 C₂₀H₂₂O₈ 
• 1385652-17-4 C₂₀H₂₂O₈ 
• 500-99-2 3,5-dimethoxyphenol 

Downstream Products

• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 
• 84212-84-0 2-(3,4-dimethoxyphenyl)-3,5,7-trimethoxy-4H-chromene-4-thione 
• 93-07-2 Veratric acid 
• 26049-25-2 (+/-)-2,3-cis-3,5,7,3',4'-Pentamethoxyflavan ((+/-)-Epicatechin-pentamethylaether) 
• 1245-15-4 retusin 
• 7380-44-1 5,8-dihydroxy-3,7-dimethoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 14965-12-9 2-(3,4-dimethoxy-phenyl)-5-hydroxy-3,7,8-trimethoxy-chromen-4-one 
• 7741-47-1 hexa-O-methylogossypetin 
• 47492-60-4 3,5,7,3',4'-penta-O-methylcyanidin 
• 66312-97-8 3,5,7,3',4'-pentamethoxyflav-2-enol 

Relevant academic research and scientific papers

O-ALKYLATION DE LA QUERCETINE ET SYNTHESE DE LA TETRA-O-EHYL-3,7,3',4' O-ETHYL -5 QUERCETINE

An efficient procedure is described for alkylation of quercetin with alkyl halides by use of tetraethylammonium fluoride in DMF or HMPT.The method is applied successfully to the preparation of 3,7,3',4', tetra-O-ethyl 5 O-ethylquercetin with a specific radioactivity of 45 Ci/mmol.

STRUCTURAL ELUCIDATION OF POLYMETHOXYFLAVONES FROM SHIFT REAGENT PROTON NMR MEASUREMENTS

Key Word Index - Polymethoxyflavones; 1H NMR; shift reagents; Pr(fod)3; structural elucidation. The quantitative shift reagent behavior of polymethoxylated flavones in the presence of Pr(fod)3 shows that for structural elucidation of these molecules the degree of substitution on the neighbourhood of the carbonyl group can be determined from the number of signals that are strongly shifted and broadened.The induced shifts of the remaining signals are of complementary help and even the resonances of individual methoxy groups can be ascribed.

A flavonol glycoside-lignan ester and accompanying acylated glucosides from Monochaetum multiflorum

Four acylated glycosides along with six known glycosides were isolated from the leaves of Monochaetum multiflorum. The new compounds were characterized as 4.0-(6′-O-galloyl- β- glucopyranosyl)-cis-p-coumaric acid, 6′-O- galloylprunasin, benzyl 6′-O-galloyl-β-glucopyranoside, and a novel diester of tetrahydroxy-μ-truxinic acid with 2 mol of hyperin (monochaetin), based on NMR and MS spectral data and chemical evidence.

Method of producing an alkoxyflavone derivative

A method of producing an alkoxyflavone derivative involves a step of reacting hydroxyflavone derivative which is shown in the below chemical formula and dialkyl sulfate in the presence of dimethyl sulfoxide and an alkali hydroxide. Further, in the chemical formula below, R11-R14, R21-R25 and R3 are independently one of hydrogen, hydroxyl group, ester group, alkoxy group, alkylenedioxy group, sulfonyl group and alkyl group, respectively. However, at least two of R21-R25 and R3 are hydroxyl groups.

Pharmacokinetics and Metabolites of 12 Bioactive Polymethoxyflavones in Rat Plasma

Polymethoxyflavones (PMFs) are a subgroup of flavonoids possessing various health benefits. 3,5,7,4′-Tetramethoxyflavone (1), 5,6,7,4′-tetramethylflavone (2), 3,7,3′,4′-tetramethoxyflavone (3), 5,7,3′,4′-tetramethoxyflavone (4), 5-hydroxy-3,7,2′,4′-tetramethoxyflavone (5), 3,5,7,2′,4′-pentamethoxyflavone (6), 5-hydroxy-3,7,3′,4′-tetramethoxyflavone (7), 3-hydroxy-5,7,3′,4′-tetramethylflavone (8), 3,5,7,3′,4′-pentamethoxyflavone (9), 5-hydroxy-3,7,3′,4′,5′-pentamethoxyflavone (10), 3-hydroxy-5,7,3′,4′,5′-pentamethoxyflavone (11), and 3,5,7,3′,4′,5′-hexamethoxylflavone (12) were 12 bioactive and available PMFs. The aim of this study was to investigate the pharmacokinetic, metabolite, and antitumor activities as well as the structure-pharmacokinetic-antitumor activity relationships of these 12 PMFs to facilitate further studies of their medicinal potentials. The cytotoxicity of PMFs with a hydroxy group toward HeLa, A549, HepG2, and HCT116 cancer cell lines was generally significantly more potent than that of PMFs without a hydroxy group. Compounds 5, 7, 8, 10, and 11 were all undetectable in rat plasma, while compounds 1-4, 6, 9, and 12 were detectable. Both the number and position of hydroxy and methoxy groups played an important role in modulating PMF pharmacokinetics and metabolites.

Unraveling the anti-influenza effect of flavonoids: Experimental validation of luteolin and its congeners as potent influenza endonuclease inhibitors

The biological effects of flavonoids on mammal cells are diverse, ranging from scavenging free radicals and anti-cancer activity to anti-influenza activity. Despite appreciable effort to understand the anti-influenza activity of flavonoids, there is no clear consensus about their precise mode-of-action at a cellular level. Here, we report the development and validation of a screening assay based on AlphaScreen technology and illustrate its application for determination of the inhibitory potency of a large set of polyols against PA N-terminal domain (PA-Nter) of influenza RNA-dependent RNA polymerase featuring endonuclease activity. The most potent inhibitors we identified were luteolin with an IC50 of 72 ± 2 nM and its 8-C-glucoside orientin with an IC50 of 43 ± 2 nM. Submicromolar inhibitors were also evaluated by an in vitro endonuclease activity assay using single-stranded DNA, and the results were in full agreement with data from the competitive AlphaScreen assay. Using X-ray crystallography, we analyzed structures of the PA-Nter in complex with luteolin at 2.0 ? resolution and quambalarine B at 2.5 ? resolution, which clearly revealed the binding pose of these polyols coordinated to two manganese ions in the endonuclease active site. Using two distinct assays along with the structural work, we have presumably identified and characterized the molecular mode-of-action of flavonoids in influenza-infected cells.

Correlation study on methoxylation pattern of flavonoids and their heme-targeted antiplasmodial activity

A library of 33 polymethoxylated flavones (PMF) was evaluated for heme-binding affinity by biomimetic MS assay and in vitro antiplasmodial activity on two strains of P. falciparum. Stability of heme adducts was discussed using the dissociation voltage at 50% (DV50). No correlation was observed between the methoxylation pattern and the antiparasitic activity, either for the 3D7 chloroquine-sensitive or for the W2 chloroquine-resistant P. falciparum strains. However, in each PMF family an increased DV50 was observed for the derivatives methoxylated in position 5. Measurement of intra-erythrocytic hemozoin formation of selected derivatives was performed and hemozoin concentration was inversely correlated with heme-binding affinity. Kaempferol showed no influence on hemozoin formation, reinforcing the hypothesis that this compound may exert in vitro antiplasmodial activity mostly through other pathways. Pentamethoxyquercetin has simultaneously demonstrated a significant biological activity and a strong interaction with heme, suggesting that inhibition of hemozoin formation is totally or partially responsible for its antiparasitic effect.

A simple and effective preparation of quercetin pentamethyl ether from quercetin

Among the five hydroxy (OH) groups of quercetin (3,5,7,3',4'-pentahydroxyflavone), the OH group at 5 position is the most resistant to methylation due to its strong intramolecular hydrogen bonding with the carbonyl group at 4 position. Thus, it is generally difficult to synthesize the pentamethyl ether efficiently by conventional methylation. Here, we describe a simple and effective perO-methylation of quercetin with dimethyl sulfate in potassium (or sodium) hydroxide/dimethyl sulfoxide at room temperature for about 2 hours, affording quercetin pentamethyl ether (QPE) quantitatively as a single product. When methyl iodide was used in place of dimethyl sulfate, the C-methylation product 6-methylquercetin pentamethyl ether was also formed. A computational study provided a rationale for the experimental results.

Synthesis of Benzopyran-Fused Flavone Derivatives via Microwave-Assisted Intramolecular C-H Activation

A microwave-assisted intramolecular direct arylation method for the synthesis of benzopyran-fused flavone derivatives containing natural flavone backbones is described. Different polyalkoxy flavones were synthesized and functionalized with 2-bromobenzyl bromide. The resulting compounds were subjected to palladium-catalyzed intramolecular direct arylation reactions supported by microwave irradiation to produce fused tetracyclic flavones. In the case of the 7-substituted chrysin derivative, the regioselectivity of the coupling was also examined.

Flavonoid aromatizing enzyme inhibitor as well as preparation method and application thereof

The invention relates to a flavonoid aromatizing enzyme inhibitor. Through cyanomethylation reaction and alkylation reaction, some substituted groups on the mother ring of a flavonoid compound are changed and a series of flavonoid compounds and derivatives thereof are synthesized. The structural general formula can be shown in the general formula in claims. In the structural general formula, R1 isselected from any one of -OH or -H, R2 is selected from any one of -H, -OCH3 or -OH, R3 is selected from any one of -H, -OH, -OCH2CN or -OCH3, R4 is selected from any one of -H, -OH, -CH2Ph or -2-(2-methoxy-2-oxo ethyl)benzyloxy, R5 is selected from any one of -H, -OCH2Ph or -OCH3, and R6 is selected from any one of -H, -OH or -OCH3. The flavonoid compounds have good inhibition effect on aromatizing enzyme; through activity test, the maximal value IC50 of inhibiting the activity of the aromatizing enzyme by the inhibitor is equal to 0.251 [mu]mol/L.