6344-24-7

Usage

Classification

Flavonoid 2-(2-chlorophenyl)-2,3-dihydro-4H-chromen-4-one is classified as a flavonoid, which is a type of natural pigment found in plants.

Structure

Chromen-4-one The compound has a chromen-4-one structure, which is a heterocyclic compound with a benzopyranopyrone skeleton.

Chlorophenyl group

Benzene ring with chlorine substituent It contains a chlorophenyl group, which is a benzene ring with a chlorine atom attached.

Biological activities

Potential pharmacological effects 2-(2-chlorophenyl)-2,3-dihydro-4H-chromen-4-one may have various biological activities and potential pharmacological effects, making it of interest for research and potential medical applications.

Upstream product

• 67765-45-1 (+)-(2S,4S)-2'-chloroflavan-4-ol 
• 36136-61-5 2-chloro-2'-hydroxychalcone 
• 936183-74-3 tert-butyl (E)-3-(2-chlorophenyl)-2-(2-hydroxyphenylcarbonyl)prop-2-enoate 
• 118-61-6 2-hydroxy-benzoic acid ethyl ester 
• 936182-86-4 tert-butyl 3-(2-hydroxyphenyl)-3-oxopropanoate 
• 89-98-5 2-chloro-benzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 491-38-3 1-benzopyran-4(4H)-one 
• 694-80-4 2-bromo-1-chlorobenzene 
• 145626-24-0 (E)-1-(2-hydroxy-phenyl)-3-(2-chloro-phenyl)-prop-2-en-1-one 
• 1101612-72-9 C₂₀H₁₉ClO₄ 

Downstream Products

• 116115-48-1 2'-Chloroflavone 
• 1400900-06-2 3-(3,4-dimethoxybenzylidene)-2'-chloroflavanone 
• 1400900-18-6 C₃₂H₂₈ClNO₄S 
• 1400900-17-5 C₃₁H₂₆ClNO₄S 
• 1400900-16-4 C₃₁H₂₆ClNO₃S 
• 1400900-15-3 C₃₀H₂₃BrClNO₃S 
• 1400900-14-2 C₃₀H₂₃Cl₂NO₃S 
• 1400900-13-1 C₃₀H₂₃ClFNO₃S 
• 534569-41-0 C₁₆H₁₄ClN₃O₂ 

Relevant academic research and scientific papers

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

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 and kinetic investigations for the isomerization process of 2–hydroxy chalcone derivatives

The wide biological activities of flavanones are mainly depends on their physical and chemical properties, thus a number of substituted 2-Hydroxy chalcones have been synthesized, and their isomerization to their corresponding flavanones was studied. In order to determine the rate constant, kinetic experiments were performed using HPLC technique in (9:1) (CH3CN:H2O) medium at different temperature (298-318) K. The obtained results were interpreted by four steps mechanism, which considered the existence of phenoxide ion as the key intermediate. This study performed with a pseudo first order (reaction in which the rate for the studied compounds follow the sequence 5 > 2 > 1 > 4 > 3, the activation energy have the same sequence for these compounds .The effect of substituents on the rate showed that electronic and steric factors play reasonable role on the stability of the product .

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.

Direct α-Arylation/Heteroarylation of 2-Trifluoroboratochromanones via Photoredox/Nickel Dual Catalysis

Utilizing photoredox/nickel dual catalysis, diverse flavanones have been synthesized by coupling novel 2-trifluoroboratochromanone building blocks with aryl and heteroaryl bromide partners. The newly reported trifluoroboratochromanones can be easily accessed from the corresponding chromones on multigram scale. This represents a general route for accessing natural and unnatural flavanones that were previously formed through a synthetically more restrictive ring closure route from chalcone precursors.

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.

Facile one-pot synthesis of flavanones using tetramethylguanidinum-based ionic liquids as catalysts

Several tetramethylguanidinum-based ionic liquids (TMGILs) were prepared, characterized and used as catalysts in one-pot synthesis of flavanones. The results indicated that TMGILs composed of phenolate anion was beneficial for one-pot synthesis of flavanones, and [TMG][4-MeO-PhO] induced the good yields of flavanones owing to the electron-donating effect of methoxy substituent on phenolate anion. Furthermore, [TMG][4-MeO-PhO] was found to be used repetitively at least five times without obvious decrease in activity and quantity.

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.

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.

Highly efficient and green synthesis of flavanones and tetrahydroquinolones

Highly efficient and green catalytic conversion of 2′-hydroxy and 2′-amino chalcones to flavanones and tetrahydroquinolones is reported herein. 2′-Hydroxy and 2′-amino chalcones can be almost completely converted to flavanones and tetrahydroquinolones in just 2 min in the presence of piperidine and KOH under room temperature. Liquiritigenin is also efficiently synthesized under similar conditions.