126784-71-2

Upstream product

• 60313-84-0 (+)-(2S,4S)-4'-chloroflavan-4-ol 
• 52923-39-4 (E)-2'-hydroxy-4-chlorochalcone 
• 1469-94-9 1-(2-hydroxyphenyl)-3-phenyl-1,3-propanedione 
• 104-88-1 4-chlorobenzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 5101-44-0 2-ethynyl-phenol 
• 491-38-3 1-benzopyran-4(4H)-one 
• 1679-18-1 4-Chlorophenylboronic acid 
• 533-58-4 2-Iodophenol 
• 22105-07-3 3-(4-chlorophenyl)-1-(2-hydroxyphenyl)propan-1-one 
• 108-95-2 phenol 
• 491-37-2 2,3-dihydro-4H-1-benzopyran-4-one 
• 3055-86-5 3-phenoxypropionitrile 
• 873-73-4 4-n-chlorophenylacetylene 

Downstream Products

• 10420-75-4 4'-chloroflavone 
• 132351-67-8 3-(4-chlorophenyl)-4H-1-benzopyran-4-one 
• 138846-95-4 2-(4-chlorophenyl)-3,4-dihydro-5-benzodioxepin-4-one 
• 60313-84-0 (+/-)-cis-4'-chloroflavan-4-ol 
• 534569-36-3 C₁₆H₁₄ClN₃O₂ 
• 89839-97-4 4'-chloro-4α-phenoxyflavan 
• 73110-68-6 2-(4-chloro-phenyl)-chroman 
• 1234138-44-3 C₂₁H₁₇ClN₂O 
• 1234138-27-2 4-(4-chlorophenyl)-2-phenyl-2,4-dihydrochromeno[4,3-c]pyrazole 
• 1292299-68-3 C₂₁H₁₆Cl₂N₂O 
• 1292299-76-3 2,4-bis(4-chlorophenyl)-2,4-dihydrochromeno[4,3-c]pyrazole 
• 1370351-79-3 4-(4-chlorophenyl)-1-phenyl-1,4-dihydrochromeno[4,3-c]pyrazole 
• 1370351-80-6 1,4-bis(4-chlorophenyl)-1,4-dihydrochromeno[4,3-c]pyrazole 
• 1370351-81-7 4-(4-chlorophenyl)-1-(4-methoxyphenyl)-1,4-dihydrochromeno[4,3-c]pyrazole 

Relevant academic research and scientific papers

A new synthesis of flavanones

Flavanones 2 were synthesized in good yields from 3-chloro-2,3-dihydro-3-nitro-2-phenyl-4H-1-benzopyran-4-ones 1 using a free radical process involving the tributyltin hydride/2,2'-azobisisobutyronitrile system in refluxing benzene.

Direct synthesis and catalytic reactivity of highly ordered large-pore methylaminopropyl-functionalized SBA-15 materials

Highly ordered large-pore SBA-15 materials functionalized with a high loading of amino groups were synthesized for the first time by co-condensation of tetraethyl orthosilicate (TEOS) and [3-(methylamino)propyl]trimethoxysilane (MAPTMS) using an amphiphilic block copolymer. Addition of inorganic salt to the initial mixture greatly enhanced the mesostructure ordering and stability of the mesoporous materials. The materials thus obtained showed high catalytic activity and selectivity for the synthesis of flavanones by means of the Claisen-Schmidt condensation in the absence of solvent. CSIRO 2005.

Not only AIE: Light-sensitivity of 4-dimethylamino-2′-hydroxychalcones beneficial to highly efficient photochemical synthesis of 4′-dimethylaminoflavanones

4-dimethylamino-2′-hydroxychalcone in crystals is well known for its aggregation induced emission (AIE) in the red region of spectrum. We however observe that in liquid solutions this dye and its analogues undergo reversible wavelength-dependent light-induced cyclization to the flavanone derivatives. Special care thus should be taken when this compound is used for optoelectronic applications requiring high purity, especially via solution-processed methods. The discussed intramolecular cyclization proceeds faster in nonpolar medium and is quenched completely in the presence of protic solvents or via formation of aggregates in crystal phase. In spite of that quantum yield of a single photoinduced transformation does not exceed 1%, continuous irradiation affords 92% of product which makes it the most efficient preparation route for 4′-dimethylminoflavanone and its derivatives among the ones reported before. According to the DFT and TDDFT calculations supported by the experimentally investigated spectral features, the mechanism of photoinduced formation of a 4′-dimethylaminoflavanone involves several transformations: excited state intramolecular proton transfer (ESIPT), excited and ground state rotational isomerization from s-trans to s-cis isomer, cyclization and enol-keto tautomerization via proton transfer in the ground state.

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.

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.

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 study for the interconversion process of some 2'-hydroxychalcones to their corresponding flavanones

In this work, five substituted2'-Hydroxychalconeswere prepared using Claisen - Schmidt condensation and used as a synthone for substituted flavanones via base catalyzed isomerization process. The latter process has been studied kinetically using HPLC technique in (8:2) (CH3CN:CH3OH) medium at different temperatures (298 K - 318 K). The obtained results were inconsonance with a four-step mechanism which considered the existence of phenoxide ion as the key intermediate. The reaction was achieved as a pseudo first order reaction in which the rate of the studied compounds followed the sequence 1>2>3>4>5, and the activation energy had the same sequence for these compounds. The reaction rate was affected by the electronic behavior of the different substituents at ring B since they played an important role in the stability of the intermediate that led to the final product.

Organocatalytic Approach for Assembling Flavanones via a Cascade 1,4-Conjugate Addition/oxa-Michael Addition between Propargylamines with Water

A DBU-catalyzed one-pot cascade reaction of propargylamines and water for the synthesis of flavanones has been developed. This process proceeds via a sequence of 1,4-conjugate addition of water to alkynyl o-quinone methide (o-AQM), followed by the alkyne-allene isomerization and subsequent intramolecular oxa-Michael addition. This strategy provides a convenient method for accessing a broad range of flavanones in good to excellent yields with good functional-group tolerance, in particular, the reactive halo functional groups.

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.