55977-09-8

Usage

InChI:InChI=1/C15H10O4/c16-10-5-3-4-9(8-10)15-14(18)13(17)11-6-1-2-7-12(11)19-15/h1-8,16,18H

Upstream product

• 76666-32-5 3'-Methoxyflavonol 
• 121245-86-1 1-(2-hydroxyphenyl)-3-(3-hydroxyphenyl)prop-2-en-1-one 
• 118-93-4 o-hydroxyacetophenone 
• 100-83-4 meta-hydroxybenzaldehyde 
• 591-31-1 3-methoxy-benzaldehyde 
• 22924-15-8 3-ethoxybenzaldehyde 
• 296237-05-3 2-(3-ethoxyphenyl)-3-hydroxy-4H-chromen-4-one 

Downstream Products

• 119045-06-6 3-Ethoxy-2-(3-hydroxy-phenyl)-chromen-4-one 
• 119045-07-7 2-(3-Hydroxy-phenyl)-3-isopropoxy-chromen-4-one 
• 119045-05-5 2-(3-Hydroxy-phenyl)-3-methoxy-chromen-4-one 
• 1309445-45-1 C₂₉H₂₈O₁₃ 
• 1344994-73-5 C₄₃H₄₆O₂₂ 

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.

A 3 - hydroxy flavone and its derivatives of aqueous phase one-pot synthesis method (by machine translation)

The invention belongs to the field of chemical synthesis, in particular to a 3 - hydroxy flavone and its derivatives of the one-pot synthesis method of the aqueous phase. The invention relates to 2 - hydroxy acetophenone and its derivatives with the benzaldehyde and its derivatives as the substrate of reaction, or 2 - hydroxy chalcone and its derivatives as the substrate of reaction, water or ethanol aqueous solution as the solvent, under the aerobic condition, 20 - 100 °C, reaction to obtain 3 - hydroxy flavone and its derivatives. The present invention provides a new reaction mechanism, has developed an efficient, convenient, wide adaptability of the substrate 3 - hydroxy flavone synthesis method; the invention also the use of the new method to synthesize a brand-new 3 - hydroxy flavone derivatives, in the health care field has important application value. (by machine translation)

Phototransformations of some 3-cyclohexenyloxychromenones: Synthesis of Spirocyclic compounds

The phototransformation of the 3-cyclohexenyloxychromenones by irradiation with a pyrex-filtered light from a 125 W Hg vapor lamp under an inert atmosphere into the spirocyclic fused xanthenones was described. The efficacy of the protocol depended upon th

Profiling of flavonol derivatives for the development of antitrypanosomatidic drugs

Flavonoids represent a potential source of new antitrypanosomatidic leads. Starting from a library of natural products, we combined target-based screening on pteridine reductase 1 with phenotypic screening on Trypanosoma brucei for hit identification. Flavonols were identified as hits, and a library of 16 derivatives was synthesized. Twelve compounds showed EC50 values against T. brucei below 10 μM. Four X-ray crystal structures and docking studies explained the observed structure-activity relationships. Compound 2 (3,6-dihydroxy-2-(3-hydroxyphenyl)-4H-chromen-4-one) was selected for pharmacokinetic studies. Encapsulation of compound 2 in PLGA nanoparticles or cyclodextrins resulted in lower in vitro toxicity when compared to the free compound. Combination studies with methotrexate revealed that compound 13 (3-hydroxy-6-methoxy-2-(4-methoxyphenyl)-4H-chromen-4-one) has the highest synergistic effect at concentration of 1.3 μM, 11.7-fold dose reduction index and no toxicity toward host cells. Our results provide the basis for further chemical modifications aimed at identifying novel antitrypanosomatidic agents showing higher potency toward PTR1 and increased metabolic stability.

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,

Novel synthesis of 3,3′-dihydroxyflavone and apparent formation constants of flavonoid-Ga(III) Complexes

Flavonoids are a wide variety of polyphenolic compounds. They have many biological properties. They also exhibit a metallic ion complexation capacity, which is important since it has been found that biological properties these ligands present can be enhan

On the antioxidant properties of three synthetic flavonols

The antioxidant properties of a series of synthetic and natural flavonoids towards the oxygenated species superoxide radical anion (O2 .-) enzimatically generated, were evaluated. 7-Hydroxyflavonol, 7,3′-dihydroxyflavonol and 3′-hydr

Effect of flavonol derivatives on the carrageenin-induced paw edema in the rat and inhibition of cyclooxygenase-1 and 5-lipoxygenase in vitro.

Alkoxyflavonols were synthesized by the Algar-Flynn-Oyamada (AFO) cyclization of chalcones. Hydroxyflavonols were prepared by dealkylation of methoxyflavonols by refluxing in hydroiodic acid. The alkoxyflavonols 3-hydroxy-2-(2,3,4-trimethoxyphenyl)-4H-chr