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Usage

Uses

Used in Pharmaceutical Applications:
4H-1-Benzopyran-4-one,7-hydroxy-2-(2-hydroxyphenyl)-(9CI) is used as a bioactive compound for its diverse pharmacological properties. 4H-1-Benzopyran-4-one,7-hydroxy-2-(2-hydroxyphenyl)-(9CI)'s ability to bind to biomolecules and chelate transition metal ions makes it a promising candidate for the development of new drugs targeting various diseases and conditions.
Used in Antioxidant Applications:
In the field of antioxidant research, 4H-1-Benzopyran-4-one,7-hydroxy-2-(2-hydroxyphenyl)-(9CI) is used as a free radical scavenger. Its capacity to neutralize free radicals can help protect cells from oxidative damage, which is a significant factor in the development of various diseases, including cancer, cardiovascular diseases, and neurodegenerative disorders.
Used in Drug Delivery Systems:
4H-1-Benzopyran-4-one,7-hydroxy-2-(2-hydroxyphenyl)-(9CI) can be employed as a component in drug delivery systems, where its ability to bind to biomolecules and chelate transition metal ions can enhance the delivery, bioavailability, and therapeutic outcomes of various drugs.
Used in Chemical Research:
In the chemical research industry, 4H-1-Benzopyran-4-one,7-hydroxy-2-(2-hydroxyphenyl)-(9CI) is used as a starting material or intermediate for the synthesis of more complex molecules with potential applications in various fields, including pharmaceuticals, agrochemicals, and materials science.

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

Upstream product

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• 90-02-8 salicylaldehyde 
• 108-46-3 recorcinol 
• 21615-34-9 2-Methoxybenzoyl chloride 
• 829-20-9 2',4'-dimethoxyacetophenone 
• 855602-63-0 2-methoxy-benzoic acid-(2-acetyl-5-methoxy-phenyl ester) 
• 856814-85-2 1-(2-hydroxy-4-methoxy-phenyl)-3-(2-methoxy-phenyl)-propane-1,3-dione 
• 36685-63-9 (E)-2,4-dimethoxy-2'-hydroxychalcone 
• 606-45-1 2-methoxybenzoic acid methyl ester 
• 63487-16-1 2-(2,4-dimethoxyphenyl)-4H-chromen-4-one 
• 62536-78-1 7-methoxy-2-(2-methoxyphenyl)-4H-chromen-4-one 

Relevant academic research and scientific papers

MACROPHYLLOSIDE, A FLAVONE GLUCOSIDE FROM PRIMULA MACROPHYLLA

A new flavone glucoside macrophylloside has been isolated from the whole plant of Primula macrophylla and its structure was determined by spectroscopic methods as 2'-hydroxy-7-O-β-D-glucopyranosyloxyflavone.Sitosterol glucoside was also isolated for the first time from this plant. Key Word Index - Primula macrophylla; Primulaceae; flavone glucoside; macrophylloside; 2'-hydroxy-7-O-β-D-glucopyranosyloxyflavons.

Design, synthesis and evaluation of novel 7-aminoalkyl-substituted flavonoid derivatives with improved cholinesterase inhibitory activities

A novel series of 7-aminoalkyl-substituted flavonoid derivatives 5a-5r were designed, synthesized and evaluated as potential cholinesterase inhibitors. The results showed that most of the synthesized compounds exhibited potent acetylcholinesterase (AChE) and butyrylcholinesterase (BChE) inhibitory activities at the micromolar range. Compound 2-(naphthalen-1-yl)-7-(8-(pyrrolidin-1-yl)octyloxy)-4H-chromen-4-one (5q) showed the best inhibitory activity (IC50, 0.64 μM for AChE and 0.42 μM for BChE) which were better than our previously reported compounds and the commercially available cholinergic agent Rivastigmine. The results from a Lineweaver-Burk plot indicated a mixed-type inhibition for compound 5q with AChE and BChE. Furthermore, molecular modeling study showed that 5q targeted both the catalytic active site (CAS) and the peripheral anionic site (PAS) of AChE. Besides, these compounds (5a-5r) did not affect PC12 and HepG2 cell viability at the concentration of 10 μM. Consequently, these flavonoid derivatives should be further investigated as multipotent agents for the treatment of Alzheimer's disease.

N-Disubstituted carbamoyloxy flavones

The invention relates to new flavone derivaties which have at least one N-disubstituted carbamoyloxy unit (OOCNR6(R7))coupled directly to one or both aromatic rings of the flavone molecule.

Synthesis of flavonoids and their effects on aldose reductase and sorbitol accumulation in streptozotocin-induced diabetic rat tissues

Aldose reductase, the key enzyme of the polyol pathway, and oxidative stress are known to play important roles in the complications of diabetes. A drug with potent inhibition of aldose reductase and oxidative stress, therefore, would be a most promising drug for the prevention of diabetic complications. The purpose of this study was to develop new compounds with these dual-effects through synthesis of chalcone derivatives and by examining the structure-activity relationships on the inhibition of rat lens aldose reductase as well as on antioxidant effects. A series of 35 flavonoid derivatives were synthesized by Winget's condensation, oxidation, and reduction of appropriate acetophenones with appropriate benzaldehydes. The inhibitory activity of these derivatives on rat lens aldose reductase and their antioxidant effects, measured using Cu2+ chelation and radical scavenging activities on 1,1-diphenyl-picrylhydrazyl in-vitro, were evaluated. Their effect on sorbitol accumulation in the red blood cells, lenses and sciatic nerves of streptozotocin-induced diabetic rats was also estimated. Among the new flavonoid derivatives synthesized, those with the 2′,4′-dihydroxyl groups in the A ring such as 2,4,2′,4′-tetrahydroxychalcone (22), 2,2′,4′-trihydroxychalcone (11), 2′,4′-dihydroxy-2,4-dimethylchalcone (21) and 3,4,2′,4′-tetrahydroxychalcone (18) were found to possess the highest rat lens aldose reductase inhibitory activity in-vitro, their IC50 values (concentration of inhibitors giving 50 % inhibition of enzyme activity) being 1.6 × 10-7, 3.8 × 10-7, 4.0 × 10-7 and 4.6 × 10-7 M, respectively. All of the chalcones tested except 3, 18, 23 with o-dihydroxy or hydroquinone moiety showed a weak free radical scavenging activity. In the in-vivo experiments, however, compound 18 with o-dihydroxy moiety in the B ring showed the strongest inhibitory activity in the accumulation of sorbitol in the tissues. It also showed the strongest activity in transition metal chelation and free radical scavenging activity. Of the 35 4,2′-dihydroxyl and 2′,4′-dihydroxyl derivatives of flavonoid synthesized, including chalcone, flavone, flavanone, flavonol and dihydrochalcone, some chalcone derivatives synthesized were found to possess aldose reductase inhibition and antioxidant activities in-vitro as well as inhibition in the accumulation of sorbitol in the tissues in-vivo. 3,4,2′,4′-Tetrahydroxychalcone (18, butein) was the most promising compound for the prevention or treatment of diabetic complications.