93176-00-2

Usage

Uses

Used in Pharmaceutical Industry:
6-METHOXYFLAVONOL is used as a pharmaceutical intermediate for the preparation of spirobenzofuranones. These spirobenzofuranones are valuable compounds with potential therapeutic applications, including anticancer, anti-inflammatory, and antioxidant properties.
Used in Chemical Synthesis:
6-METHOXYFLAVONOL serves as a key building block in the synthesis of various complex organic molecules and natural products. Its unique structure allows for further functionalization and modification, making it a versatile starting material for the development of new pharmaceuticals and agrochemicals.
Used in Research and Development:
6-METHOXYFLAVONOL is utilized in research laboratories for studying the structure-activity relationships of flavonoids and their derivatives. It helps scientists understand the molecular mechanisms underlying the biological activities of these compounds and aids in the design of more effective and targeted therapeutic agents.

InChI:InChI=1/C16H12O4/c1-19-11-7-8-13-12(9-11)14(17)15(18)16(20-13)10-5-3-2-4-6-10/h2-9,18H,1H3

Upstream product

• 3034-04-6 6-methoxyflavanone 
• 99430-03-2 2'-hydroxy-5'-methoxychalcone 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 100-52-7 benzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 59-88-1 phenylhydrazine hydrochloride 
• 93175-95-2 6-methoxy-3-nitro-2-phenyl-2H-chromene 

Downstream Products

• 123-31-9 hydroquinone 
• 65-85-0 benzoic acid 
• 1242087-46-2 3-Hydroxy-6-methoxyflavone 3-glucuronide 
• 1233689-16-1 3-(allyloxy)-6-methoxy-2-phenyl-4H-chromen-4-one 

Relevant academic research and scientific papers

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.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.

Ruthenium(II)-Catalyzed Synthesis of Spirobenzofuranones by a Decarbonylative Annulation Reaction

The first decarbonylative insertion of an alkyne through C?H/C?C activation of six-membered compounds is reported. The Ru-catalyzed reaction of 3-hydroxy-2-phenyl-chromones with alkynes works most efficiently in the presence of the ligand PPh3 to provide spiro-indenebenzofuranones. Unlike previously reported metal-catalyzed decarbonylative annulation reactions, in the present decarbonylative annulation reaction, the annulation occurs before extrusion of carbon monoxide.

Hydroxyl directed: C -arylation: Synthesis of 3-hydroxyflavones and 2-phenyl-3-hydroxy pyran-4-ones under transition-metal free conditions

An efficient, transition-metal free and direct C-arylation of 3-hydroxychromone moieties in the presence of a base, air as an oxidant and arylhydrazines as arylating agents to furnish highly biologically active flavonols or 3-hydroxyflavones has been developed. We have further extended our methodology for the C-arylation of the 5-hydroxy pyran-4-one moiety. The role of the free hydroxyl group towards C-arylation has been delineated.

Exploring the anti-breast cancer potential of flavonoid analogs

In the course of our search for new antitumor agents for breast cancer, novel flavone derivatives were synthesized, characterized and examined for their antitumor activities against breast cancer cell lines. In initial screening, analogs 7a [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-phenyl-4H-chromen-4-one] and 7b [3-(5-amino-1,3,4-thiadiazol-2-yl)methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one] were found to be effective against the estrogen receptor negative cell line (MDA-MB 453), which was followed by their evaluation in five dose assays. In addition, mechanistic studies of 7a and 7b were performed by cytometric analysis and electrophoretic studies and it was observed that apoptosis is a mechanism of cell death, confirmed morphologically by acridine orange/ethidium bromide double staining and TUNEL analysis. Further in vivo evaluation of the anti-tumor activity of compound 7a and 7b by Ehrlich Ascites Carcinoma (EAC) model and related studies confirms the anti-breast cancer potential of flavonoid analogs.

Pharmacophore model of the quercetin binding site of the SIRT6 protein

SIRT6 is a histone deacetylase that has been proposed as a potential therapeutic target for metabolic disorders and the prevention of age-associated diseases. We have previously reported on the identification of quercetin and vitexin as SIRT6 inhibitors,

A NOVEL SYNTHESIS OF 6-METHOXY AND 7-METHOXY FLAVONOLS

Condensation of 4-methoxy- (1) or 5-methoxy- (2) salicylaldehyde with ω-nitrostyrene (3-6) in the presence of triethylamine yields 7-methoxy or 6-methoxy-3-nitro-2H-flavene (7-13), which on treatment with alkaline hydrogen peroxide yields the correspondin