1098-92-6

Usage

Uses

Used in Pharmaceutical Industry:
4',5,7-Trimethoxyflavonol is used as a potential therapeutic agent for its antioxidant properties, which may help in combating oxidative stress-related diseases. Its anti-inflammatory effects could also be beneficial in treating inflammatory conditions.
Used in Cancer Research:
4',5,7-Trimethoxyflavonol is used as a subject of research in cancer studies due to its potential anti-cancer properties. 4',5,7-Trimethoxyflavonol may contribute to the development of novel cancer treatments or prevention strategies, given the general anti-cancer effects attributed to flavonoids.
Used in Cardiovascular Health Applications:
4',5,7-Trimethoxyflavonol is used as a cardioprotective agent in research and development, with the aim of understanding its potential to protect the heart and improve cardiovascular health, based on the cardioprotective effects of flavonoids.
Used in Nutraceutical Industry:
4',5,7-Trimethoxyflavonol is used as an ingredient in nutraceutical products for its potential health benefits, including its antioxidant and anti-inflammatory properties, which may contribute to overall wellness and disease prevention.

Upstream product

• 74351-52-3 C₄₄H₆₂O₁₉ 
• 621-23-8 1,2,3-trimethoxybenzene 
• 35492-16-1 (+/-)-3-hydroxy-4',5,7-trimethoxy-2,3-trans-flavanone 
• 147437-71-6 ω-benzoyloxy-4,6-dimethoxy-2-hydroxyacetophenone 
• 794-94-5 p-Methoxybenzoic anhydride 
• 123-11-5 4-methoxy-benzaldehyde 
• 16692-52-7 3,4',5,7-tetramethoxyflavone 
• 520-18-3 kaempferol 
• 83768-75-6 2-hydroxy-1-(2-hydroxy-4,6-dimethoxyphenyl)ethan-1-one 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 500-99-2 3,5-dimethoxyphenol 
• 3420-72-2 flavokawain A 
• 26207-83-0 (+/-)-3t-hydroxy-2r-(4-hydroxy-phenyl)-5,7-dimethoxy-chroman-4-one 
• 65982-77-6 2-benzoyloxy-1-(2,4,6-trihydroxy-phenyl)-ethanone 

Downstream Products

• 16692-52-7 3,4',5,7-tetramethoxyflavone 
• 520-18-3 kaempferol 
• 77316-40-6 5,7-dimethoxy-3-hydroxy-2-(4-hydroxyphenyl)-4H-chromen-4-one 
• 1467042-70-1 1-[N-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)]-4-[3-O-methylene-(7,5,4’-trimethoxy flavonol)]-[1,2,3]-triazole 
• 1469990-08-6 1-(N-β-D-glucotopyranosyl)-4-[3-O-methylene-(7,5,4’-trimethoxy flavonol)]-[1,2,3]-triazole 
• 1467042-79-0 1-(N-β-D-galactopyranosyl)-4-[3-O-methylene-(7,5,4’-trimethoxy flavonol)]-[1,2,3]-triazole 
• 1469989-89-6 1-[N-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyl)]-4-[3-O-methylene-(7,5,4’-trimethoxy flavonol)]-[1,2,3]-triazole 
• 1467042-67-6 5,7-dimethoxy-2-(4-methoxyphenyl)-3-(prop-2-yn-1-yloxy)-4H-chromen-4-one 

Relevant academic research and scientific papers

Total synthesis of kaempferol and methylated kaempferol derivatives

Kaempferol (1), a natural product from various plants, was synthesized in which the longest linear sequence is only seven steps in overall yields of 47% from commercially available 1,3,5-trimethoxybenzene (10). The methylated kaempferols 2-5 were also prepared by use of this concise synthetic methodology. The key transformations in this synthesis involved the I2 oxidative-promoting-cyclization and DDO oxidative hydroxylation. Several strategies to achieve 1 are provided.

Dual-Targeting Antiproliferation Hybrids Derived from 1-Deoxynojirimycin and Kaempferol Induce MCF-7 Cell Apoptosis through the Mitochondria-Mediated Pathway

1-Deoxynojirimycin, an α-glucosidase inhibitor, possesses various biological activities such as antitumor, antidiabetic, and antiviral effects. However, the application of 1-deoxynojirimycin is restricted by its poor lipophilicity and low bioavailability.

Flavonol glycosides from Cassia hirsuta

A new flavonol glycoside, kaempferol 3-O-α-L-rhamnopyranosyl (1→2)- α-L-rhamnopyranoside (1), was isolated from the flowers of Cassia hirsuta along with two known flavonol glycosides, kaempferol 3-O-rutinoside and rutin. The structure of compound 1 has been established on the basis of spectral data and by acid hydrolysis.

MASS SPECTROMETRY IN THE STRUCTURAL DETERMINATION OF FLAVONOL TRIGLYCOSIDES FROM VINCA MAJOR

Key Word Index-Vinca major; Apocynaceae; leaves; flavonol glycosides; kaempferol 3-O-(6''-O-rhamnosyl)-galactosides 7-O-glucoside; chlorogenic acid; mass spectrometry.Chlorogenic acid, robinin and flavonol triglycoside were isolated from the leaves of Vinca major.The structure of the triglycoside was determined to be kaempferol 3-O-(6''-rhamnopyranosyl)-galactopyranoside 7-O-glucopyranoside by fast atom bombardment, electron impact and negative ion desorption chemical ionization mass spectropetry.

Synthesis of Flavonols via Pyrrolidine Catalysis: Origins of the Selectivity for Flavonol versus Aurone

A novel synthetic method for flavonol from 2′-hydroxyl acetophenone and benzaldehyde promoted by pyrrolidine under an aerobic condition in water is established. This protocol was supported by efficient synthesis of 44 common examples and three natural products. The α, β-unsaturated iminium ion (enimine ion E) was proved to be the key intermediate in the reaction. H218O and 18O2 isotope tracking experiments demonstrated that both water and the aerobic atmosphere were necessary to ensure the transformation. The selectivity for flavonol or aurone was originated from solvent-triggered intermediates, which were determined by UV-visible spectra from isolated enimine. The phenol-iminium E-A is dominant in water and the ketoenamine intermediate E-B is prevalent in acetonitrile. In the presence of pyrrolidine and oxygen, E-A leads to flavonol through E-I, a zwitterionic-like phenoloxyl-iminium ion, following the key steps of cyclization and a [2 + 2] oxidation; E-B proceeds through path II, a radical process induced by photolysis of E-B with both pyrrolidine and oxygen, to afford aurone. Preliminary mechanistic studies are reported.

1-deoxynojirimycin-kaempferol compound, intermediate, preparation method and application

The invention discloses a 1-deoxynojirimycin-kaempferol compound, an intermediate, a preparation method and application. The structural formula of the compound is as shown in the specification. In thestructural formula, R is -CnH2n-, n is an integer, and

Chemical Synthesis Enables Structural Reengineering of Aglaroxin C Leading to Inhibition Bias for Hepatitis C Viral Infection

As a unique rocaglate (flavagline) natural product, aglaroxin C displays intriguing biological activity by inhibiting hepatitis C viral entry. To further elucidate structure-activity relationships and diversify the pyrimidinone scaffold, we report a concise synthesis of aglaroxin C utilizing a highly regioselective pyrimidinone condensation. We have prepared more than 40 aglaroxin C analogues utilizing various amidine condensation partners. Through biological evaluation of analogues, we have discovered two lead compounds, CMLD012043 and CMLD012044, which show preferential bias for the inhibition of hepatitis C viral entry vs translation inhibition. Overall, the study demonstrates the power of chemical synthesis to produce natural product variants with both target inhibition bias and improved therapeutic indexes.

Intercepted Retro-Nazarov Reaction: Syntheses of Amidino-Rocaglate Derivatives and Their Biological Evaluation as eIF4A Inhibitors

Rocaglates are a family of natural products isolated from the genus Aglaia which possess a highly substituted cyclopenta[b]benzofuran skeleton and inhibit cap-dependent protein synthesis. Rocaglates are attractive compounds due to their potential for inhibiting tumor cell maintenance in vivo by specifically targeting eukaryotic initiation factor 4A (eIF4A) and interfering with recruitment of ribosomes to mRNA. In this paper, we describe an intercepted retro-Nazarov reaction utilizing intramolecular tosyl migration to generate a reactive oxyallyl cation on the rocaglate skeleton. Trapping of the oxyallyl cation with a diverse range of nucleophiles has been used to generate over 50 novel amidino-rocaglate (ADR) and amino-rocaglate derivatives. Subsequently, these derivatives were evaluated for their ability to inhibit cap-dependent protein synthesis where they were found to outperform previous lead compounds including the rocaglate hydroxamate CR-1-31-B.

Flavone derivative and medical application thereof

The invention provides a flavone derivative and medical application thereof, and belongs to the technical field of medicines. Specifically, the invention relates to a compound as shown in a formula Iand a pharmacological effect thereof for regulating cell

Synthesis and biological evaluation of flavones and benzoflavones as inhibitors of BCRP/ABCG2

Multidrug resistance (MDR) often leads to a failure of cancer chemotherapy. Breast Cancer Resistance Protein (BCRP/ABCG2), a member of the superfamily of ATP binding cassette proteins has been found to confer MDR in cancer cells by transporting molecules with amphiphilic character out of the cells using energy from ATP hydrolysis. Inhibiting BCRP can be a solution to overcome MDR.We synthesized a series of flavones, 7,8-benzofl avones and 5,6-benzo flavones with varying substituents at positions 3, 3′ and 4′ of the (benzo)fl avone structure. All synthesized compounds were tested for BCRP inhibition in Hoechst 33342 and pheophorbide A accumulation assays using MDCK cells expressing BCRP. All the compounds were further screened for their P-glycoprotein (P-gp) and Multidrug resistance-associated protein 1 (MRP1) inhibitory activity by calcein AM accumulation assay to check the selectivity towards BCRP. In addition most active compounds were investigated for their cytotoxicity. It was observed that in most cases 7,8-benzoflavones are more potent in comparison to the 5,6-benzoflavones. In general it was found that presence of a 3-OCH3 substituent leads to increase in activity in comparison to presence of OH or no substitution at position 3. Also, it was found that presence of 3′,4′-OCH3 on phenyl ring lead to increase in activity as compared to other substituents. Compound 24, a 7,8-benzoflavone derivative was found to be most potent being 50 times selective for BCRP and showing very low cytotoxicity at higher concentrations.