84638-53-9

Upstream product

• 552-41-0 1-(2-hydroxy-4-methoxyphenyl)ethanone 
• 123-08-0 4-hydroxy-benzaldehyde 
• 4397-53-9 p-benzyloxybenzaldehyde 
• 63529-06-6 4,2'-dihydroxy-4'-methoxy-trans-chalcone 
• 111391-50-5 2-[4-(benzyloxy)phenyl]-3-hydroxy-7-methoxy-4H-chromen-4-one 

Downstream Products

• 84638-54-0 3-acetoxy-2-(4-acetoxy-phenyl)-7-methoxy-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.

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)

3′-Hydroxy-3,4′-dimethoxyflavone blocks tubulin polymerization and is a potent apoptotic inducer in human SK-MEL-1 melanoma cells

Flavonoids are naturally occurring polyphenolic compounds and are among the most promising anticancer agents. A series of flavonols and their 3-methyl ether derivatives were synthesized and assessed for cytotoxicity. It was found that 3′-hydroxy-3,4′-dime

Chromenones derivatives with strong cardiac activating function and pharmaceutical composition containing thereof for preventing or treating heart failure

Method for preventing or treating composition of the present invention novel compress maul rice field derivatives and including of heart failure, ventricular muscle contraction has excellent effect of increasing myocardial myosin ATPase activation effect, can be useful for the prevention or treatment of heart failure drug. (by machine translation)

Exploration of Pharmacophore in Chrysosplenol C as Activator in Ventricular Myocyte Contraction

Chrysosplenol C (4',5,6-trihydroxy-3,3',7-trimethoxyflavone) isolated from Miliusa balansae has unique structural features as a reversible inotropic agent independent of β-adrenergic signaling and with selective activation of cardiac myosin ATPase. Hence, a series of chrysosplenol analogues were synthesized and explored for identification of pharmacophore that is essential for the increasing contractility in rat ventricular myocytes. Analogue 7-chloro-2-(3-hydroxyphenyl)-3-methoxy-4H-chromen-4-one showed highly potent contractility (54.8% at 10 μM) through activating cardiac myosin ATPase (38.7% at 10 μM). Our systematic structure-activity relationship study revealed that flavonoid nucleus of chrososplenol C appears to be an essential basic skeleton and hydrophobic substituent at position 7 of chromenone such as methoxy or chloro enhances the activity. Additionally, our ATPase study suggested that these chrysosplenol analogues have selectivity toward cardiac myosin activation. Thus, the novel flavonone with 3-/7-hydrophobic substituent and 3'-hydrogen bonding donor function is a novel scaffold for discovery of a new positive inotropic agent.

OXYGENATION OF 4-HYDROXYCHALCONES CATALYSED BY PEROXIDASE AND BY LIGHT

Peroxidase or light catalysed oxygenation of 2',4-dihydroxy-4'-methoxychalcone produced two labile initial products characterized as stereoisomers of 4'-hydroxy-6-methoxy-2-(α-hydroperoxybenzyl)coumaranone.By analogy, the products from similar oxygenation reactions of 2',4,4'-trihydroxychalcone previously studied are now considered to be hydroperoxy-benzylcoumaranones rather than dioxetanes. - Keywords: Oxygenation; photooxygenation; peroxidase; 4-hydroxychalcones; 2',4-dihydroxy-4'-methoxychalcone.