29080-58-8

Usage

Uses

Used in Pharmaceutical Applications:
5-Hydroxy-3',4',7-trimethoxyflavone is used as a potential therapeutic agent for its potential health benefits, such as antioxidative, anti-inflammatory, and anti-carcinogenic properties. These properties may contribute to the development of new drugs or supplements for various health conditions.
Used in Dietary Supplements:
5-Hydroxy-3',4',7-trimethoxyflavone is used as an ingredient in dietary supplements, leveraging its potential health benefits to support overall well-being and promote a healthy lifestyle.
Used in Chemical Research:
5-Hydroxy-3',4',7-trimethoxyflavone is used as a subject of study in chemical research, where its properties and potential applications are explored to better understand its role in various fields, such as medicine, nutrition, and agriculture.
Used in Medical Applications:
5-Hydroxy-3',4',7-trimethoxyflavone is used as a potential component in medical treatments, with its potential health benefits being investigated for their applicability in addressing specific health issues or conditions.

InChI:InChI=1/C18H16O6/c1-21-11-7-12(19)18-13(20)9-15(24-17(18)8-11)10-4-5-14(22-2)16(6-10)23-3/h4-9,19H,1-3H3

Upstream product

• 186581-53-3 diazomethane 
• 491-70-3 2-(3,4-Dihydroxy-phenyl)-5,7-dihydroxy-chromen-4-on 
• 4712-12-3 5,7-dihydroxy-3',4'-dimethoxy flavone 
• 77-78-1 dimethyl sulfate 
• 74-88-4 methyl iodide 
• 2174-64-3 5-methoxyresorcinol 
• 4687-37-0 ethyl 3,4-dimethoxybenzoylacetate 
• 520-34-3 diosmetin 
• 10544-05-5 2-(3,4-dimethoxy-phenyl)-7-hydroxy-5-methoxy-chromen-4-one 
• 74628-44-7 7,3′,4′-O-trimethyltaxifolin 
• 33554-52-8 3′-hydroxy-5,7,4′-trimethoxyflavone 
• 114021-60-2 2'-hydroxy-3,4,4',6'-tetramethoxychalcone 
• 75917-11-2 5-hydroxy-6,3',4'-trimethoxyflavanone 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 

Downstream Products

• 71847-58-0 5,8-dihydroxy-7-methoxy-2-(3,4-dimethoxyphenyl)-4-benzopyrone 
• 2174-64-3 5-methoxyresorcinol 
• 93-07-2 Veratric acid 
• 855-97-0 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-4H-chromen-4-one 
• 13003-74-2 5-hydroxy-3’,4’,7,8-tetramethoxyflavone 
• 117-39-5 quercetol 
• 1244-78-6 2-(3,4-dimethoxyphenyl)-3-hydroxy-5,7-dimethoxy-4H-4-chromenone 
• 1245-15-4 retusin 
• 1247-97-8 pentamethyl quercetin 
• 17290-70-9 isosinensetin 
• 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 
• 1638743-79-9 6-(N,N-diethylaminomethyl)-5-hydroxy-7,3',4'-trimethoxyflavone 

Relevant academic research and scientific papers

Synthesis of 5-Hydroxy-3′,4′,7-trimethoxyflavone and Related Compounds and Elucidation of Their Reversal Effects on BCRP/ABCG2-Mediated Anticancer Drug Resistance

3′,4′,7-Trimethoxyflavone (TMF) has been reported to show a potent reversal effect on drug resistance mediated by breast cancer resistance protein (BCRP)/ATP-binding cassette subfamily G member 2 (ABCG2). In this study, we designed and synthesized five derivatives with either a hydroxy group or a fluorine atom at C-5 and several kinds of capping moiety at the C-7 hydroxy group, on the same 3′,4′-dimethoxy-substituted flavone skeleton. We subsequently evaluated the efficacies of these compounds against BCRP-expressing human leukaemia K562/BCRP cells. Reversal of drug resistance was expressed as the concentration of compound causing a twofold reduction in drug sensitivity (RI50). Of the synthesized compounds, the reversal effect of 5-hydroxy-3′,4′,7-trimethoxyflavone (HTMF, RI50 7.2 nm) towards 7-ethyl-10-hydroxycamptothecin (SN-38) was stronger than that of TMF (RI50 18 nm). Fluoro-substituted 5-fluoro-3′,4′,7-trimethoxyflavone (FTMF, RI50 25 nm) and monoglycosylated 7-(β-glucosyloxy)-5-hydroxy-3′,4′-dimethoxyflavone (GOHDMF, 91 nm) also exhibited reversal effects, whereas the di- and triglycoside derivatives did not. TMF, HTMF and FTMF at 0.01–10 μm upregulated the K562/BCRP cellular accumulation of Hoechst 33342 nuclear staining dye. In addition, western blotting revealed that treatment of K562/BCRP cells with 0.1 μm TMF, HTMF or FTMT suppressed the expression of BCRP. HTMF showed the strongest inhibition of BCRP-mediated efflux and suppression of BCRP expression of the three effective synthesized flavones.

Synthesis and Antiproliferative Activity of Thioxoflavones Mannich Base Derivatives

Two series of 12 novel thioxoflavones Mannich base derivatives 5a–f and 6a–f were synthesized via Mannich reaction of 4′,7-dimethoxy-5-hydroxyflavothione (3) or 3′,4′,7-trimethoxy-5-hydroxyflavothione (4) with appropriate aliphatic amines or alicyclic amines and formaldehyde. Thioxoflavones 3 and 4 were prepared from 4′,7-dimethoxy-5-hydroxyflavone (1) and 3′,4′,7-trimethoxy-5-hydroxyflavone (2) with Lawesson's reagent, respectively. Their antiproliferative activities in vitro were evaluated on a panel of three human cell lines (HeLa, HCC1954, and SK-OV-3) by CCK-8 assay. The results showed that most of the thioxoflavones and their Mannich base derivatives exhibited potential antiproliferative activities on the tested cancer cell lines, with IC50 values ranging from 9.16 to 55.50 μM. In particular, thioxoflavone 4 and the thioxoflavone Mannich base derivatives 5a and 5d showed the best antiproliferative activity on all three human cancer cell lines; they are promising candidates worthy of further development. The structures of all synthesized compounds were confirmed by 1H NMR, 13C NMR, IR, and MS techniques.

Anti‐melanogenic properties of velutin and its analogs?

Velutin, one of the flavones contained in natural plants, has various beneficial activities, such as skin whitening, as well as anti‐inflammatory, anti‐allergic, antioxidant, and antimicrobial activities. However, the relationship between the structure of velutin and its anti‐melanogenesis activity is not yet investigated. In this study, we obtained 12 velutin derivatives substituted at C5, C7, C3′, and C4′ of the flavone backbone with hydrogen, hydroxyl, and methoxy functionalities by chemical synthesis, to perform SAR analysis of velutin structural analogues. The SAR study revealed that the substitution of functional groups at C5, C7, C3′, and C4′ of the flavone backbone affects biological activities related to melanin synthesis. The coexistence of hydroxyl and methoxy at the C5 and C7 position is essential for inhibiting tyrosinase activity. However, 1,2‐diol compounds substituted at C3′ and C4′ of flavone backbone induce apoptosis of melanoma cells. Further, substitution at C3′ and C4′ with methoxy or hydrogen is essential for inhibiting melanogenesis. Thus, this study would be helpful for the development of natural‐derived functional materials to regulate melanin synthesis.

Synthesis, in Silico and in vitro evaluation of some flavone derivatives for Acetylcholinesterase and BACE-1 inhibitory activity

Acetylcholinesterase (AChE) and β-secretase (BACE-1) have become attractive therapeutic targets for Alzheimer’s disease (AD). Flavones are flavonoid derivatives with various bioactive effects, including AChE and BACE-1 inhibition. In the present work, a series of 14 flavone derivatives was synthesized in relatively high yields (35–85%). Six of the synthetic flavones (B4, B5, B6, B8, D6 and D7) had completely new structures. The AChE and BACE-1 inhibitory activities were tested, giving pIC50 3.47–4.59 (AChE) and 4.15–5.80 (BACE-1). Three compounds (B3, D5 and D6) exhibited the highest biological effects on both AChE and BACE-1. A molecular docking investigation was conducted to explain the experimental results. These molecules could be employed for further studies to discover new structures with dual action on both AChE and BACE-1 that could serve as novel therapies for AD.

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.

Substituted flavonoid compound and its preparation and use

The invention relates to the technical field of biological medicines, and firstly provides a flavonoid compound shown as a general formula (I) and an application of the flavonoid compound in preparation of an anti-tumor medicine. In addition, the invention further provides a medicine composition containing the flavonoid compound. The flavonoid compound can be competitively combined with Bcl-2, Bcl-xL and Mcl-1 protein so as to specifically cause the apoptosis of tumor cells, so that the flavonoid compound can be possibly developed into a safe and efficient anti-cancer medicine of targeted Bcl-2 family protein. In addition, the compound provided by the invention also has good antifungal activity. Thus, based on data, the compound provided by the invention has good development prospects.

Acidic rearrangement of benzyl group in flavone benzyl ethers and its regioselectivity

Abstract The benzyl-substituted flavone compounds are rare in nature, while some of which have interesting biological activities. The total synthesis of benzyl-substituted flavone derivatives via the acidic rearrangement of benzyl groups in flavone benzyl ethers, and the complicated regioselectivity of the rearrangement were reported. The regioselectivity was proposed to be determined by the steric hindrance as well as the ease of electrophilic substitution reaction for benzyl cations at different positions of corresponding debenzylated flavone compounds.

Synthesis and anticholinesterase inhibitory activity of mannich base derivatives of flavonoids

Hesperidin-derived 2'-hydroxy-3,4,4',6'-tetramethoxy-chalcone and 5-hydroxy-7,3',4'-trimethoxy-flavone underwent reaction with formaldehyde and a series of secondary amines producing 11 new Mannich base derivatives of flavonoids. The aminomethylation occurred preferentially at the C-3' position of the chalcone and at the C-6 position of flavone. These aminated derivatives of flavonoids were evaluated as inhibitors of acetylcholinesterase (AChE) and the results showed that two of them exhibited excellent AChE inhibitory activity.

NMR of a series of novel hydroxyflavothiones

Alkylated hydroxyflavothiones, namely flavothione, 5-hydroxyflavothione, 5,7-dihydroxyflavothione (chrysinthione), 7-dodecyloxy-5-hydroxyflavothione, 7-butyloxy-5-hydroxyflavothione, 2′,3,4′,7-tetramethoxy-5- hydroxyflavothione, 3,3′,4′,7-tetramethoxy-5-hydroxyflavothione, 7-butyloxy-4′,5-dihydroxyflavothione and 7-butyloxy-4′,5- hydroxyflavanonethione have been synthesized from the corresponding hydroxyflavones in two steps, alkylation of the non-hydrogen-bonded hydroxyl groups by bromoalkanes or dimethyl sulfate followedby conversion of the carbonyl group to a thione using Lawesson's Reagent undermicrowave irradiation and solvent-free conditions. Part of the alkylated flavanone, 7-butyloxy-4′,5- dihydroxyflavanone, was oxidized during the treatment with Lawesson's reagent to yield a second product 7-butyloxy-4′,5-dihydroxyflavothione in addition to the target product butyloxy-4′,5-hydroxyflavanonethione. Deuterium isotope effects on 13C chemical shifts have been measured in hydroxyflavones, isoflavones, flavanones and the thio analogs. Formal four-bond deuterium isotope effects on 13C chemical shifts, nΔC= S(OD) are very sensitive to variations in structures and substitution patterns. Density functional theory (DFT) calculations are carried out to obtain geometries. Correlations relating distances around the hydrogen bond system to the deuterium isotope effects on 13C chemical shifts are discussed. 13C chemical shifts are calculated by DFT methods. Effects of thiocarbonyl anisotropies are suggested.

Chromenone derivatives useful for the treatment of neurodegenerative diseases

Compounds of general formula (I) and (II) in which R1, R2, R3, R4, R5, R6, R7, R8, R9, R10, R11, R12, R13, R14 and R15 have the meanings given in the specification, are useful in the treatment of neurodegenerative disease.