6697-63-8

Upstream product

• 105285-13-0 2,3-dihydro-5-methoxy-2-(4-methoxyphenyl)-4H-1-benzopyran-4-one 
• 1466-76-8 2-6-dimethoxybenzoic acid 
• 768-60-5 4-methoxyphenylacetylen 
• 123-11-5 4-methoxy-benzaldehyde 
• 703-23-1 2'-hydroxy-6'-methoxyacetophenone 
• 699-83-2 2,6-dihydroxylacetophenone 
• 105285-09-4 (E)-1-(2-hydroxy-6-methoxyphenyl)-3-(4-methoxyphenyl)prop-2-en-1-one 

Downstream Products

• 745-39-1 5,4'-diacetoxyflavanone 
• 6665-72-1 4'-Methoxy-5-hydroxyflavone 
• 6665-67-4 5,4'-dihydroxyflavone 

Relevant academic research and scientific papers

Metal-free methodology for the preparation of sterically hindered alkynoylphenols and its application to the synthesis of flavones and aurones

A metal-free synthesis for the preparation of sterically demanding ortho-demethylated ynones from mixed anhydrides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without the exclusion of air and moisture. This method is advantageous in that it is operationally simple, proceeds under mild conditions, and has a broad substrate scope. 2,6-Dimethoxy substituted anhydrides afford the corresponding mono-demethylated ynone products in good yields. In particular, 2-hydroxy substituted ynone products are valuable synthetic intermediates because their conversion to biologically active natural product scaffolds is straightforward. Flavones were obtained via 6-endo cyclization of the o-alkynyoylphenol intermediates under acidic conditions. Cesium carbonate was found to promote rapid 5-exo cyclization to furnish aurone products.

Synthesis and inhibitory activity against COX-2 catalyzed prostaglandin production of chrysin derivatives

A series of chrysin derivatives were prepared and evaluated for their inhibitory activities of cyclooxygenase-2 catalyzed prostaglandin production. Chrysin derivatives were prepared from 2-hydroxyacetophenone, 2,4-dihydroxyacetophenone and 2,6-dihydroxyacetophenone in 2 to 4 steps, respectively. Methxoylated chrysin derivatives were converted to the corresponding hydroxylated chrysin derivatives by the reaction with BBr 3 in good yields. The inhibitory activity of the chrysin derivatives against prostaglandin production from lipopolysaccharide-treated RAW 264.7 cells was measured. We found that chrysin derivatives with 3′,4′- dichloro substituents (5e, 6e and 7e) exhibited good inhibitory activity of prostaglandin production.