67765-54-2

Upstream product

• 7146-86-3 3-methoxy-2'-hydroxychalcone 
• 32865-61-5 2-iodophenyl acetate 
• 179248-84-1 1-(3-methoxyphenyl)prop-2-yn-1-ol 
• 261785-30-2 3-(o-acetoxyphenyl)-1-(m-methoxyphenyl)prop-2-yn-ol 
• 34000-28-7 2'-hydroxy-3-methoxy-chalcone 
• 118-93-4 o-hydroxyacetophenone 
• 591-31-1 3-methoxy-benzaldehyde 
• 491-38-3 1-benzopyran-4(4H)-one 
• 10365-98-7 3-methoxyphenylboronic acid 
• 53906-83-5 3'-methoxyflavone 
• 3055-86-5 3-phenoxypropionitrile 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 108-95-2 phenol 

Downstream Products

• 75848-98-5 1-(2-hydroxyphenyl)-3-(3-methoxyphenyl)propan-1-ol 
• 76666-32-5 3'-Methoxyflavonol 
• 7146-86-3 3-methoxy-2'-hydroxychalcone 
• 53906-83-5 3'-methoxyflavone 
• 153000-44-3 3-(3-methoxyphenyl)-4H-chromen-4-one 
• 73110-71-1 2-(3-methoxy-phenyl)-chroman 
• 140479-97-6 2-[3-(3-methoxyphenyl)propyl]phenol 
• 140480-01-9 2-{3-(3-Methoxy-phenyl)-3-[2-(3-methoxy-phenyl)-chroman-6-yl]-propyl}-phenol 

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.

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.

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.

Glycosylation of methoxylated flavonoids in the cultures of isaria fumosorosea KCH J2

Flavonoids are widely described plant secondary metabolites with high and diverse pro-health properties. In nature, they occur mostly in the form of glycosides. Our research showed that an excellent way to obtain the sugar derivatives of flavonoids is thr

A Borane-Catalyzed Metal-Free Hydrosilylation of Chromones and Flavones

A Piers-type hydrosilylation of chromones and flavones has been successfully realized for the first time using 0.1 mol % of borane catalyst generated in situ by hydroboration of pentafluorostyrene with HB(C 6 F 5) 2 to afford a variety of chromanones and flavanones in 60-99% yields. An attempt for the asymmetric transformation with chiral diyne and HB(C 6 F 5) 2 gave chromanones and flavanones in high yields with up to 32% ee.

An efficient synthesis of flavanones and their docking studies with aldose reductase

A series of flavanone derivatives have been synthesized from 2-hydroxy acetophenone and benzaldehyde using fused calcium chloride in good to moderate yields, and their in vitro aldose reductase inhibitory activity has been tested on aldose reductase purified enzyme from Bovine lens. Most of the synthesized compounds exhibited potent aldose reductase inhibitory activity, and the obtained results are supported by the docking studies. Among the tested derivatives, 2, 3, 4-methoxy derivative 19 (IC50 5.88 ± 0.03 μM) exhibited the highest inhibitory activity whereas 2-methoxy derivative 12 showed the lowest, and the remaining compounds exhibited moderate activity with IC50 in the range of 6.09–7.89 μM. The spatial configuration of the most active derivative 19 was compared with pharmacophore requirements of the aldose reductase inhibitor site using a molecular modeling system.

Rhodium/chiral diene-catalyzed asymmetric 1,4-addition of arylboronic acids to chromones: A highly enantioselective pathway for accessing chiral flavanones

Chromone has been noted to be one of the most challenging substrates in the asymmetric 1,4-addi-tion of α,β-unsaturated carbonyl compounds. By employing the rhodium complex associated with a chiral diene ligand, (R,R)-Ph-bod, the 1,4-addition of a variety of aryl-boronic acids was realized to give high yields of the corresponding flavanones with excellent enantioselectivities (≥97% ee, 99% ee for most substrates). Ring-opening side products, which would lead to erosion of product enantioselectivity, were not observed under the stated reaction conditions.

SAR studies of o-hydroxychalcones and their cyclized analogs and study them as novel inhibitors of cathepsin B and cathepsin H

Cathepsins have emerged as a potential target for anti-cancer drug development. In the present study, we have synthesized three structurally related series of flavanoids i.e., 2′-hydroxychalcones, flavanones and flavones and assayed in vitro to study their inhibitory potency against cathepsin B and H, promising drug candidate for cancer therapy. Enzyme kinetics studies were carried out in presence of these compounds after preliminary proteolytic studies on endogenous protein substrates. SAR studies suggested that open chain flavanoids were better inhibitors as compared to their cyclized analogs. The most potent inhibitors among the three series were nitro substituted compounds 1g, 2g and 3g with Ki values of ～6.18 × 10-8 M, 4.8 × 10-7 M and 7.85 × 10-7 M for cathepsin B and Ki values of ～2.8 × 10-7 M, 31.8 × 10-6 M and 33.7 × 10 -6 M for cathepsin H, respectively. The relationship between chalcone, flavanones and flavone structures interpreted by docking studies on cathepsin B and H also provided useful insights.

Fe(HSO4)3/SiO2: An efficient and heterogeneous catalyst for one-pot synthesis of 2-aryl-chromene-4-ones (flavanones)

Silica ferric hydrogensulphate is an efficient heterogeneous catalyst for cyclisation of 2-hydroxychalcones to their corresponding flavanones (chromanone). This intramolecular oxa-Michael reaction was carried out in high yields in the presence of electron donating and electron withdrawing groups in the chalcone structure. Also, we found that aniline can act as an organic co-catalyst in direct synthesis of flavanones from 2-hydroxyacethophenone and aldehydes in the presence of Fe(HSO4)3/SiO2. Flavanones were prepared in high yields in a new catalytic system with similar substituted effect in the indirect cyclisation method. The catalyst in all the above reactions is reusable without significant decreases in its activity after four times of recycling.

Mild and efficient one-pot synthesis of diverse flavanone derivatives via an organocatalyzed Mannich-type reaction

A facile ethylenediamine diacetate (EDDA)-catalyzed one-pot synthesis of biologically interesting flavanone derivatives from 2-hydroxyacetophenones, aromatic aldehydes, and aniline via a Mannich-type reaction is described. This synthetic method provides a rapid access to biologically interesting flavanone derivatives. To demonstrate this method, several biologically interesting natural products bearing a flavanone moiety were synthesized as racemates.