53906-83-5

Usage

Class

Flavone (a subclass of flavonoids)

Physical State

Yellow crystalline solid

Natural Sources

Found in parsley, chamomile, celery, and other plant sources

Pharmacological Properties

Anti-inflammatory: Potential to reduce inflammation
Antioxidant: Ability to combat oxidative stress
Anti-cancer: Investigated for potential cancer-fighting properties

Enzyme Inhibition

Acts as an inhibitor of cytochrome P450

Potential Applications

Drug Metabolism: Could impact drug metabolism pathways
Drug Interactions: Potential for influencing drug interactions

Ongoing Research

Continual investigation into its medicinal and biotechnological applications

InChI:InChI=1/C16H12O3/c1-18-12-6-4-5-11(9-12)16-10-14(17)13-7-2-3-8-15(13)19-16/h2-10H,1H3

Upstream product

• 34000-28-7 2'-hydroxy-3-methoxy-chalcone 
• 7146-86-3 3-methoxy-2'-hydroxychalcone 
• 67765-54-2 2,3-dihydro-2-(3-methoxyphenyl)-4H-1-benzopyran-4-one 
• 88348-41-8 2-(3-methoxyphenyl)-2H-chromene 
• 84634-65-1 1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)-1,3-propanedione 
• 591-31-1 3-methoxy-benzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 325142-84-5 3-methoxyphenylboronic acid pinacol ester 
• 586-38-9 3-Methoxybenzoic acid 
• 56030-38-7 3-methoxycinnamoyl chloride 
• 108-95-2 phenol 
• 90-02-8 salicylaldehyde 
• 253684-23-0 1,1-dibromo-2-(3-methoxyphenyl)ethene 

Downstream Products

• 70460-18-3 3'-hydroxyflavone 
• 256464-68-3 3'-methoxy-4-thioflavone 
• 902149-11-5 C₂₂H₁₆N₄O₆ 
• 127179-85-5 (+)-2-(3-methoxyphenyl)chroman-4-one 
• 67765-54-2 2,3-dihydro-2-(3-methoxyphenyl)-4H-1-benzopyran-4-one 

Relevant academic research and scientific papers

CF3SOCl-promoted intramolecular cyclization of β-diketones: An efficient synthesis of flavones

An efficient intramolecular cyclization reaction of β-diketones containing a phenyl group with an ortho-hydroxyl substituent was achieved. Using CF3SOCl as an additive, the reaction took place under transition-metal-free and mild conditions. A series of flavones were synthesized in moderate to excellent yields.

A novel one-pot synthesis of flavones

In this paper, a one-pot facile route for the BiCl3/RuCl3-mediated synthesis of functionalized flavones is described, including: (i) intermolecularortho-acylation of substituted phenols with cinnamoyl chlorides, and (ii) intramolecular cyclodehydrogenation of the resultingo-hydroxychalcones. The reaction conditions are discussed herein.

Design, synthesis and biological evaluation of substituted flavones and aurones as potential anti-influenza agents

We designed a series of substituted flavones and aurones as non-competitive H1N1 neuraminidase (NA) inhibitors and anti-influenza agents. The molecular docking studies showed that the designed flavones and aurones occupied 150-cavity and 430-cavity of H1N1-NA. We then synthesized these compounds and evaluated these for cytotoxicity, reduction in H1N1 virus yield, H1N1-NA inhibition and kinetics of inhibition. The virus yield reduction assay and H1N1-NA inhibition assay demonstrated that the compound 1f (4-methoxyflavone) had the lowest EC50 of 9.36 nM and IC50 of 8.74 μM respectively. Moreover, kinetic studies illustrated that compounds 1f and 2f had non-competitive inhibition mechanism.

Rh-Catalyzed aldehydic C-H alkynylation and annulation

Novel Rh-catalyzed aldehydic C-H bond alkynylation and annulation for the in situ synthesis of chromones and aurones are described. It involves the sequential aldehyde C-H bond alkynylation of salicylaldehyde with in situ generated 1-bromoalkyne from 1,1-

Temperature-Controlled Stereodivergent Synthesis of 2,2′-Biflavanones Promoted by Samarium Diiodide

In this work, the first example of a radical stereodivergent reaction directed towards the stereoselective synthesis of both (R*,R*)- and (R*,S*)-2,2′-biflavanones promoted by samarium diiodide is reported. Control experiments showed that the selectivity of this reaction was exclusively controlled by the temperature. It was possible to generate a variety of 2,2′-biflavanones bearing different substitution patterns at the aromatic ring in good-to-quantitative yields, being both stereoisomers of the desired compounds obtained with total or high control of selectivity. A mechanism that explains both the generation of the corresponding 2,2′-biflavanones and the selectivity is also discussed. The structure and stereochemistry determination of each isomer was unequivocally elucidated by single-crystal X-ray diffraction experiments.

One-Pot Allan–Robinson/Friedl?nder Route to Chromen-/Quinolin-4-ones through the Domino Acetylative Cyclisation of 2-Hydroxy-/2-Aminobenzaldehydes

The domino synthesis of 2-phenyl-4H-chromen-4-ones and quinolin-4-ones through acetylation of 2-hydroxy-/2-aminobenzaldehydes with α-haloketones followed by intramolecular oxa-/azaheterocyclisation is reported. This method represents a new extension of the Allan–Robinson and Friedl?nder reactions, and uses N-heterocyclic-carbene catalysis to construct the target molecules in good to excellent yields: 86–95 % for the chromen-4-ones, and 83–96 % for the quinolin-4-ones. This approach has the advantages of operational simplicity, ambient reaction conditions, and no by-product formation.

Silica-gel-supported Ce(SO4)2·4H2O-mediated cyclization of 2′-amino and 2′-hydroxychalcones under solvent-free conditions

A simple, efficient, and environmentally friendly approach for the synthesis of flavones, aza-flavones, and aza-flavanones from corresponding 2′-hydroxy or 2′-aminochalcones has been developed. The reactions are successfully conducted in presence of silica-gel-supported Ce(SO4)2·4H2O under solvent-free conditions.

Synthesis of 4H-Chromen-4-one Derivatives by Intramolecular Palladium-Catalyzed Acylation of Alkenyl Bromides with Aldehydes

The palladium-catalyzed intramolecular acylation of alkenyl bromides and aldehydes was developed for an efficient synthesis of 4H-chromen-4-ones. With Pd(PPh3)4/Xphos as the catalyst and K2CO3 as the base, this protocol was applied to synthesize a small library of diversely functionalized flavonoids in moderate to good yields in 1,4-dioxane.

Identification and structure activity relationship of novel flavone derivatives that inhibit the production of nitric oxide and PGE2 in LPS-induced RAW 264.7 cells

In an effort to identify novel anti-inflammatory compounds, a series of flavone derivatives were synthesized and biologically evaluated for their inhibitory effects on the production of nitric oxide (NO) and prostaglandin E2 (PGE2), representative pro-inflammatory mediators, in LPS-induced RAW 264.7 cells. Their structure-activity relationship was also investigated. In particular, we found that compound 3g displayed more potent inhibitory activities on PGE2 production, similar inhibitory activities on NO production and less weak cytotoxicity than luteolin, a natural flavone known as a potent anti-inflammatory agent.

Mild and efficient organocatalytic method for the synthesis of flavones

A convenient and efficient organocatalytic procedure for the selective cyclization of 1,3-diketones to give aromatic substituted 4H-chromen-4-ones under mild reaction conditions using N-triflyl phosphoramide is described. Application of the described conditions is presented in a formal synthesis of (S)-flavanone.