6344-21-4

Usage

Derivative of flavone

3,4-Dimethoxyflavone

Biological activities

Anti-inflammatory, anti-cancer, and anti-oxidant properties

Therapeutic potential

Studied for its potential therapeutic effects, showing promising results in preclinical and animal studies

Significance for future research

Unique structure and diverse biological activities make it a significant compound for drug development.

Upstream product

• 118-93-4 o-hydroxyacetophenone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 19152-36-4 (E)-2'-hydroxy-3,4-dimethoxychalcone 
• 105166-58-3 2-Hydroxy-benzoic acid [2-(3,4-dimethoxy-phenyl)-chroman-(4E)-ylidene]-hydrazide 
• 116194-64-0 2-(3,4-dimethoxyphenyl)chroman-4-ol 
• 491-38-3 1-benzopyran-4(4H)-one 
• 122775-35-3 3,4-Dimethoxyphenylboronic acid 
• 86383-39-3 3-(3,4-dimethoxyphenyl)-1-(2-hydroxyphenyl)propan-1-one 
• 3055-86-5 3-phenoxypropionitrile 
• 79140-20-8 2'-hydroxy-3,4-dimethoxychalcone 
• 58113-19-2 2-hydroxy-3',4'-dimethoxychalcone 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 

Downstream Products

• 4143-62-8 3',4'-dimethoxyflavone 
• 88214-60-2 4α-chloro-3',4'-dimethoxyflavan 
• 88214-66-8 4α,3',4'-trimethoxyflavan 
• 6889-80-1 2-(3,4-dimethoxyphenyl)-3-hydroxy-4H-chromen-4-one 
• 95561-18-5 N‐{[(4‐methylphenyl)sulfonyl]oxy}‐2‐(3,4‐dimethoxyphenyl)‐2,3‐dihydro‐4H‐chromen‐4‐imine 
• 78113-65-2 (2S,3S)-3-Bromo-2-(3,4-dimethoxy-phenyl)-chroman-4-one 
• 62082-72-8 3',4'-dimethoxyflavan-4β-ol 
• 116215-62-4 10-(3,4-Dimethoxy-phenyl)-10H-4,9-dioxa-2-aza-phenanthrene-1,3-dione 
• 116215-66-8 10-(3,4-Dimethoxy-phenyl)-3,3-dioxo-2,3-dihydro-10H-4,9-dioxa-3λ⁶-thia-2-aza-phenanthren-1-one 

Relevant academic research and scientific papers

Convenient synthesis of flavanone derivatives via oxa-Michael addition using catalytic amount of aqueous cesium fluoride

A total of 36 flavanones, which included polycyclic aromatic and heterocyclic rings, were readily synthesized via oxa-Michael addition from the corresponding hydroxychalcones with a catalytic amount of aqueous cesium fluoride solution under mild conditions. This method could be applied to the scalable synthesis of eriodictyol as a known potent inhibitor of the SARS-CoV-2 spike protein.

Divergent synthesis of flavones and flavanones from 2′-hydroxydihydrochalconesviapalladium(ii)-catalyzed oxidative cyclization

Divergent and versatile synthetic routes to flavones and flavanonesviaefficient Pd(ii) catalysis are disclosed. These Pd(ii) catalyses expediently provide a variety of flavones and flavanones from 2′-hydroxydihydrochalcones as common intermediates, depending on oxidants and additives,viadiscriminate oxidative cyclization sequences involving dehydrogenation, respectively, in a highly atom-economic manner.

Synthesis and hplc-ecd study of cytostatic condensed o,n-heterocycles obtained from 3-aminoflavanones

Racemic chiral O,N-heterocycles containing 2-arylchroman or 2-aryl-2H-chromene subunit condensed with morpholine, thiazole, or pyrrole moieties at the C-3-C-4 bond were synthesized with various substitution patterns of the aryl group by the cyclization of cis- or trans-3- aminoflavanone analogues. The 3-aminoflavanone precursors were obtained in a Neber rearrangement of oxime tosylates of flavanones, which provided the trans diastereomer as the major product and enabled the isolation of both the cis- and trans-diastereomers. The cis- and transaminoflavanones were utilized to prepare three diastereomers of 5-aryl-chromeno[4,3- b][1,4]oxazines. Antiproliferative activity of the condensed heterocycles and precursors was evaluated against A2780 and WM35 cancer cell lines. For a 3-(N-chloroacetylamino)-flavan-4-ol derivative, showing structural analogy with acyclic acid ceramidase inhibitors, 0.15 μM, 3.50 μM, and 6.06 μM IC50 values were measured against A2780, WM35, and HaCat cell lines, and apoptotic mechanism was confirmed. Low micromolar IC50 values down to 2.14 μM were identified for the thiazole- and pyrrole-condensed 2H-chromene derivatives. Enantiomers of the condensed heterocycles were separated by HPLC using chiral stationary phase, HPLC-ECD spectra were recorded and TDDFT-ECD calculations were performed to determine the absolute configuration and solution conformation. Characteristic ECD transitions of the separated enantiomers were correlated with the absolute configuration and effect of substitution pattern on the HPLC elution order was determined.

Discovery of a Prenylated Flavonol Derivative as a Pin1 Inhibitor to Suppress Hepatocellular Carcinoma by Modulating MicroRNA Biogenesis

Peptidyl-prolyl cis-trans isomerase Pin1 plays a crucial role in the development of human cancers. Recently, we have disclosed that Pin1 regulates the biogenesis of miRNA, which is aberrantly expressed in HCC and promotes HCC progression, indicating the therapeutic role of Pin1 in HCC therapy. Here, 7-(benzyloxy)-3,5-dihydroxy-2-(4-methoxyphenyl)-8-(3-methylbut-2-en-1-yl)-4H-chromen-4-one (AF-39) was identified as a novel Pin1 inhibitor. Biochemical tests indicate that AF-39 potently inhibits Pin1 activity with an IC50 values of 1.008 μm, and also displays high selectivity for Pin1 among peptidyl prolyl isomerases. Furthermore, AF-39 significantly suppresses cell proliferation of HCC cells in a dose- and time-dependent manner. Mechanistically, AF-39 regulates the subcellular distribution of XPO5 and increases miRNAs biogenesis in HCC cells. This work provides a promising lead compound for HCC treatment, highlighting the therapeutic potential of miRNA-based therapy against human cancer.

Synthesis of Flavanones via Palladium(II)-Catalyzed One-Pot β-Arylation of Chromanones with Arylboronic Acids

A total of 47 flavanones were expediently synthesized via one-pot β-arylation of chromanones, a class of simple ketones possessing chemically unactivated β sites, with arylboronic acids via tandem palladium(II) catalysis. This reaction provides a novel route to various flavanones, including natural products such as naringenin trimethyl ether, in yields up to 92percent.

Water-mediated phosphorylative cyclodehydrogenation: An efficient preparation of flavones and flavanones

A new synthetic strategy utilizing POCl3-water for the conversion of 2′-hydroxychalcones to flavanones and flavones has been developed. The reagent efficiently promoted one-pot conversion of 2′-hydroxychalcones to flavones through flavanones involving cyclization and oxidative dehydrogenation. By changing the stoichiometery of the reagents, the reaction can be tuned to generate either flavanone or flavone. The developed protocol was found to be applicable for a variety of 2′-hydroxychalcones.

Synthesis, crystal structure and antitumour activity evaluation of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives

A series of 1H-thieno[2,3-c]chromen-4(2H)-one derivatives were synthesised through Knoevenagel condensation of substituted flavanones with thiazolidine-2,4-dione in ethanol in the presence of piperidine. The mechanism of the reaction was proposed. All synthesised compounds were characterised by IR, 1H NMR, 13C NMR, HRMS, and elemental analysis. The structure of 2-(3-chlorophenyl)-1H-thieno[2,3-c]chromen-4(2H)-one was confirmed by a single crystal X-ray diffraction analysis. A preliminary antitumour screening showed that 2-(2-fluorophenyl)-1H-thieno [2,3-c]chromen-4(2H)-one had moderate to good activity against A549, BGC-823, HCT116 and MDA-MB-453 cancer cell lines, and 2-(3,4-dimethoxyphenyl)-1H-thieno[2,3-c]chromen-4(2H)-one displayed similar activity against these four kinds of cancer cells compared with the reference drug.

Synthesis of flavanones using methane sulphonic acid as a greencatalystand comparision under different conditions

Flavonoids are an important class of natural products with wide range activities. Flavonoids includes flavone, flavanone, flavane & flavanol. The synthetic route invovles synthesis of chalcone followed by ring closing to give flavanone. So many catalysts were mentioned in past literature. But most efficient catalyst is methane sulphonic acid.It is easy to handle,less reaction time &easily available. Flavanones were synthesized from chalcone using methane sulphonic acid under thermal condition, microw wave and ultrasound condition.Flavanones are syntheisized in very less time compared to other conditions.

Synthesis and anti-cancer activity evaluation of new dimethoxylated chalcone and flavanone analogs

A novel series of chalcones and flavanones discriminated by the presence of a 3,4-dimethoxyphenyl moiety in their structures were synthesized as anti-cancer agents. The cytotoxicity evaluation of the analogs against the MCF-7, MDA-MB-231 (human breast can

Pyrrolidine and iodine catalyzed domino aldol-Michael-dehydrogenative synthesis of flavones

A one pot synthesis of flavones is established from 2′- hydroxyacetophenones and substituted aromatic aldehydes. The method uses domino aldol-Michael-oxidation reaction catalyzed by pyrrolidine as a base and iodine as an oxidant in dimethyl sulfoxide.