67765-55-3

Upstream product

• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 13331-27-6 m-nitrobenzene boronic acid 
• 3055-86-5 3-phenoxypropionitrile 
• 118-93-4 o-hydroxyacetophenone 
• 99-61-6 3-nitro-benzaldehyde 
• 491-38-3 1-benzopyran-4(4H)-one 
• 36574-84-2 1-(2-hydroxyphenyl)-3-(3-nitrophenyl)-2-propen-1-one 

Downstream Products

• 77038-20-1 3'-nitro-3-methylene flavanone 
• 108897-68-3 3-acetoxy-2-(3-nitro-phenyl)-chromen-4-one 
• 70460-19-4 3'-nitroflavone 
• 145013-55-4 3-(3-nitrophenyl)-4H-1-benzopyran-4-one 
• 107918-44-5 2-(3-nitro-phenyl)-chroman-3,4-dione-3-oxime 

Relevant academic research and scientific papers

Ytterbium(III) triflate: An efficient and simple catalyst for isomerization of 2′-hydroxychalcone and 2′-aminochalcones in ionic liquid

Isomerization of 2′-hydroxychalcone and 2′-aminochalcone have been investigated using ytterbium(III) trifluromethanesulfonate {Yb(OTf) 3} (30 mol %) as Lewis acid catalyst in [bmim][BF4] ionic liquid. The effect of different metal triflates as Lewis acid, catalyst loading and reaction media was studied for this isomerization reaction. Advantages of the methodology include short reaction time, excellent yields, catalytic use of Lewis acid, and recovery and reuse of the catalyst. Copyright

Glycolytic inhibition and antidiabetic activity on synthesized flavanone scaffolds with computer aided drug designing tools

Background: Diabetes mellitus is a challengeable metabolic disorder that leads to a group of complications when the HbA1c level is not maintained. Most of the existing drugs avail-able in the market in long-term use may lead to serious adverse effects. He

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.

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.

Nanosilica-supported dual acidic ionic liquid as a heterogeneous and reusable catalyst for the synthesis of flavanones under solvent-free conditions

[Figure not available: see fulltext.] A nanosilica-supported dual acidic ionic liquid on the basis of 1-methyl-3-(4-sulfobutyl)imidazolium hydrogen sulfate was synthesized and used as an efficient, green, non-corrosive, non-toxic, heterogeneous, and reusable catalyst for the synthesis of some new and known substituted flavanones. The synthesis was done by the condensation of 2'-hydroxyacetophenone with different aldehydes and the subsequent cyclization of the resulting 2'-hydroxychalcone in the presence of the catalyst. High yields of the products, short reaction times, and solvent-free conditions characterize this new method.

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.

Silica supported-double metal cyanides (DMCs): A green and highly efficient catalytic protocol for isomerisation of 2′-hydroxychalcones to flavanones

Four different double metal cyanides (NiHCFe, CrHCFe, MnHCFe and ZnHCFe) were synthesized, followed by adsorbed on silica gel and used as Lewis acid catalyst in the isomerisation of substituted 2′-hydroxychalcones to flavanones under solvent-free (dry) condition. Optimization of the reaction condition, temperature effects, DMC catalysts loading and re-useable catalytic activity were further studied during the reaction. Among these catalysts, NiHCFe at 35 mol% loading gave excellent yield (90%) at 100 C temperature in 1.15 h. Catalyst (NiHCFe) easily recovered and re-used six times without much loss of its catalytic activity which gave 80-85% product yields each time. However, these DMCs were failed to give product in the solution phase even prolonging the reaction time at reflux temperature. Similarly, isomerization of substituted 2′-aminochalcones gave 2-5% yields either in solution phase or under solvent-free condition.

An efficient and facile synthesis of flavanones catalyzed by N-methylimidazole

The use of N-methylimidazole as an efficient catalyst for the cyclization of 2'-hydroxychalcones to the corresponding flavanones in DMSO was investigated. The scope of this process was studied and various flavanones were obtained exclusively in good yields. Copyright

Synthetic approach to flavanones and flavones via ligand-free palladium(ii)-catalyzed conjugate addition of arylboronic acids to chromones

The remarkable catalytic effects of Fe(OTf)3 in the context of the Pd(ii)-catalyzed conjugate addition of arylboronic acids to chromones were observed to yield a variety of flavanones under mild conditions. The addition of catalytic amounts of DDQ and KNO2 to the reactions exclusively yielded flavone analogs. The reaction scope for the transformation was fairly broad, affording good yields of a wide range of flavanones and flavones, which are privileged structures in many biologically active compounds.

Iodine catalyzed one-pot synthesis of flavanone and tetrahydropyrimidine derivatives via Mannich type reaction

A variety of functionalized flavanone derivatives and tetrahydropyrimidine derivatives were achieved under remarkably mild conditions. The combination of good to excellent yields, a simple work-up, and the high compatibility of functional groups makes this an attractive synthetic approach to access flavanone and tetrahydropyrimidine derivatives.