529-40-8

Usage

Uses

Used in Pharmaceutical Industry:
4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE is used as a potent inhibitor for [application reason], such as targeting Mycobacterium tuberculosis, the bacteria responsible for tuberculosis. Its ability to inhibit the growth of this pathogen makes it a valuable compound for the development of new antituberculosis drugs.
Used in Research and Development:
In addition to its potential therapeutic applications, 4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE is also used as a research tool in the field of medicinal chemistry. It can be employed to study the structure-activity relationships of flavonoids and their interactions with various biological targets, contributing to the discovery of new drugs with improved efficacy and safety profiles.
Used in Drug Delivery Systems:
Similar to other bioactive compounds, 4',7-DIMETHOXY-3,3',5-TRIHYDROXYFLAVONE can be incorporated into drug delivery systems to enhance its bioavailability, stability, and targeted delivery. This may involve the use of nanoparticles, liposomes, or other advanced drug delivery technologies to improve the compound's therapeutic potential and reduce potential side effects.

InChI:InChI=1/C17H14O7/c1-22-9-6-11(19)14-13(7-9)24-17(16(21)15(14)20)8-3-4-12(23-2)10(18)5-8/h3-7,18-19,21H,1-2H3

Upstream product

• 117-39-5 quercetol 
• 77-78-1 dimethyl sulfate 
• 60444-56-6 3-acetoxy-4-methoxybenzoic acid 
• 621-59-0 isovanillin 
• 7507-89-3 2,6-dihydroxy-4-methoxy-acetophenone 
• 32174-62-2 pilloin 
• 28590-40-1 3',5-dihydroxy-4',7-dimethoxydihydroflavone 
• 520-33-2 hesperetin 
• 74-88-4 methyl iodide 
• 498548-19-9 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5-hydroxy-7-methoxy-4H-chromen-4-one 
• 498548-17-7 3-(benzyloxy)-2-(2,2-diphenylbenzo[d][1,3]dioxol-5-yl)-5,7-dihydroxy-4H-chromen-4-one 
• 357194-03-7 2-(2,2-diphenylbenzo[1,3]dioxol-5-yl)-3,5,7-trihydroxychromen-4-one 
• 153-18-4 rutin 
• 90798-12-2 3-acetoxy-4-methoxy-benzoyl chloride 

Downstream Products

• 1245-15-4 retusin 
• 101770-13-2 isorhynchospermin 
• 21736-96-9 quercatin 7,4'-dimethyl ether triacetate 

Relevant academic research and scientific papers

Flavonoid compound as well as synthesis method and application thereof

The invention relates to a semi-synthetic flavonoid compound and an anti-inflammatory application thereof. The invention belongs to the technical field of medicines, particularly relates to synthesis of derivatives of natural products and an application of the derivatives in the anti-inflammatory aspect, and more particularly relates to a synthesis method of flavonoid compounds and an application of the flavonoid compounds in the anti-inflammatory aspect. According to the method, hesperetin is taken as a raw material, flavonol aglycone is synthesized, and finally flavonoid glycoside is synthesized through debenzylation and acetyl reaction. According to the invention, 32 flavonoid compounds, including 14 flavonoid aglycones and 18 flavonoid glycosides, including 15 known compounds and 17 unreported compounds, are synthesized in total. The part of the compounds show good in-vitro anti-inflammatory activity and can become anti-inflammatory drugs or lead compounds.

Quercetin analogs with high fetal hemoglobin-inducing activity

β-Thalassemia is the major health problems in developing countries, when affected patients and healthy carriers are numerous, resulting a total absence or severe decrease in the production of β-globin chains. The use of chemical agents for increasing the production of fetal hemoglobin (HbF) by reactivating γ-globin gene to balance excess α-globin chains is an alternative therapeutic approach. Therefore, the search for molecules exhibiting the property of inducing γ-globin gene expression is of great interest. In this report, we discovered that quercetin (1), the major flavonoid isolated from the heartwoods of the medicinal plant Anaxagorea luzonensis promoted the expression of γ-globin gene. Chemical modification of 1 to fourteen methyl ether analogs (2?15) was conducted. The structures of these compounds were established on the basis of their spectroscopic data and by comparison with those of the reported values. The parent flavonoid and its chemically modified analogs were investigated for their γ-globin gene induction for the first time. The parent compound 1 exhibited less induced γ-globin gene expression than cisplatin and hemin, the positive controls. 3,4′-Di-O-methylquercetin (7), the modified analog, significantly enhanced γ-globin gene expression with 2.6-fold change at 8 μM, which was slightly higher than cisplatin and hemin. Moreover, compounds 1 and 7 displayed less cytotoxic activity against K562::ΔGγAγEGFP cells than cisplatin. Structure-activity relationship (SAR) study revealed that the methoxyl groups at the 3- and 4?-positions and the free hydroxyl group at the 7-position are required for strong HbF-inducing activity.

Synthesis of Rhamnazin and Ombuin as methylated metabolites of quercetin

The methylated metabolites of quercetin, rhamnazin and ombuin are highly likely to develop as anticancer and anti-inflammatory agents. In this study, we synthesized rhamnazin through selective methylation of quercetin hydroxyl group, which has not been reported so far. In addition, a new synthetic method was developed to correct the problems of previous synthetic method of ombuin, one of the methylated metabolites of quercetin.

Flavonoids with M1 muscarinic acetylcholine receptor binding activity

Muscarinic acetylcholine receptor- Active compounds have potential for the treatment of Alzheimer's disease. In this study, a series of natural and synthetic flavones and flavonols was assayed in vitro for their ability to inhibit radioligand binding at human cloned M1 muscarinic receptors. Several compounds were found to possess competitive binding affinity (K i = 40-110 μM), comparable to that of acetylcholine (Ki = 59 μM). Despite the fact that these compounds lack a positively-charged ammonium group under physiological conditions, molecular modelling studies suggested that they bind to the orthosteric site of the receptor, mainly through non-polar interactions.

Synthesized quercetin derivatives stimulate melanogenesis in B16 melanoma cells by influencing the expression of melanin biosynthesis proteins MITF and p38 MAPK

In order to understand the effect of structure-activity relationships on melanogenesis using B16 melanoma cells, 19 quercetin derivatives were synthesized. Among the synthesized compounds, 3-O-methylquercetin (11) and 3′,4′,7-O-trimethylquercetin (14) increased melanin content more potently than the positive control theophylline, while exhibiting low cytotoxicity. Compound 11 exhibited less melanogenesis-stimulating activity than compound 14. However, 11 increased the expression of tyrosinase and tyrosinase-related protein 1 (TRP-1) to a greater extent than 14, thereby suggesting that melanogenesis in melanoma cells does not depend solely on the expression of the enzymes catalyzing melanin biosynthesis. Furthermore, 14 also stimulated the expression of the microphthalmia-associated transcription factor (MITF) and p-p38 mitogen activated protein kinase (MAPK), while they were not increased by 11. These results suggest that 11 may enhance the expression of tyrosinase and TRP-1 by regulating the proteasomal degradation of melanogenic enzymes and/or by activating other transcriptional factors regulating enzyme expression.

Biological evaluation and SAR analysis of O-methylated analogs of quercetin as inhibitors of cancer cell proliferation

Preclinical Research Using a high-throughout screening approach, the anticancer activities of 16 O-methylated (OMe) analogs of quercetin were assessed. The structure-activity relationships showed that OMe moieties at the 4′ and/or 7 positions were important for maintaining inhibitory activities against the 16 cancer cell lines. Furthermore, when the OH groups at the 3′ and 4′ positions were both replaced by OMe moieties, anticancer activity was enhanced.

Metabolism-based synthesis, biologic evaluation and SARs analysis of O-methylated analogs of quercetin as thrombin inhibitors

In blood, quercetin is mainly found in metabolized forms. In order to study the activities of these quercetin metabolites in cardiovascular disease, 17 methylquercetin derivatives were synthesized based on metabolism in vivo, their thrombin inhibition activity were evaluated through the analyzation of prothrombin time (PT), activated partial thromboplastin time (APTT), thrombin time (TT) and fibrinogen (FIB). The results showed that 6 methylquercetin derivatives had stronger inhibitory activities than that of quercetin. Preliminary SARs analysis showed that hydroxyl groups at C-3′ and C-4′ position in the B-ring and hydroxyl group at C-3 position in the C-ring played key roles in the thrombin inhibitory activity. The findings of this study would provide information for the exploitation and utilization of quercetin as thrombin inhibitor for thrombotic disease treatment.

Structural requirements of flavonoids and related compounds for aldose reductase inhibitory activity

The methanolic extracts of several natural medicines and medicinal foodstuffs were found to show an inhibitory effect on rat lens aldose reductase. In most cases, flavonoids were isolated as the active constituents by bioassay-guided separation, and among them, quercitrin (IC50=0.15 μM), guaijaverin (0.18 μM), and desmanthin-1 (0.082 μM) exhibited potent inhibitory activity. Desmanthin-1 showed the most potent activity, which was equivalent to that of a commercial synthetic aldose reductase inhibitor, epalrestat (0.072 μM). In order to clarify the structural requirements of flavonoids for aldose reductase inhibitory activity, various flavonoids and related compounds were examined. The results suggested the following structural requirements of flavonoid: 1) the flavones and flavonols having the 7-hydroxyl and/or catechol moiety at the B ring (the 3′,4′-dihydroxyl moiety) exhibit the strong activity; 2) the 5-hydroxyl moiety does not affect the activity; 3) the 3-hydroxyl and 7-O-glucosyl moieties reduce the activity; 4) the 2-3 double bond enhances the activity; 5) the flavones and flavonols having the catechol moiety at the B ring exhibit stronger activity than those having the pyrogallol moiety (the 3′,4′,5′-trihydroxyl moiety).

FLAVONOIDS FROM ERYTHROXYLON ARGENTINUM

Quercetin 3-rutinoside, quercetin 3-α-L-rhamnoside, 7,4'-dimethylquercetin 3-rutinoside and the novel glycoside 7,4'-dimethylquercetin 3-rutinoside-5-glucoside have been identified from aerial parts of Erythroxylon argentinum. - Key Word Index - Erythroxylon argentinum; Erythroxylaceae; flavonoids; 7,4'-dimethylquercetin 3-rutinoside-5-glucoside; 7,4'-dimethylquercetin 3-rutinoside; quercetin 3α-L-rhamnoside; Quercetin 3-rutinoside.