84963-03-1

Usage

Uses

Used in Pharmaceutical Applications:
(S)-2,3-Dihydro-6-methoxy-2-phenyl-4-benzopyrone is used as a therapeutic agent for its antioxidant, anti-inflammatory, and anti-cancer properties. It has been studied for its potential to modulate cellular pathways and prevent certain diseases, making it a promising candidate for the development of novel medications.
Used in Research and Drug Discovery:
In the field of research, (S)-2,3-Dihydro-6-methoxy-2-phenyl-4-benzopyrone is used as a chemical probe to study the mechanisms of action of flavonoids. This helps researchers understand the potential of these compounds as drug candidates and contributes to the advancement of drug discovery in various therapeutic areas.
Used in Chemical Applications:
(S)-2,3-Dihydro-6-methoxy-2-phenyl-4-benzopyrone, being a flavonoid derivative, is also utilized in the chemical industry for various purposes, such as the synthesis of other compounds or as an intermediate in the production of pharmaceuticals and other products.
Overall, (S)-2,3-Dihydro-6-methoxy-2-phenyl-4-benzopyrone is a versatile compound with a wide range of applications in different industries, primarily due to its potential therapeutic effects and its use in research and drug discovery.

Upstream product

• 3033-90-7 (E)-1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 705-15-7 1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 100-52-7 benzaldehyde 
• 22867-46-5 (E)-4-methoxyphenyl cinnamate 
• 26964-24-9 6-methoxyflavone 
• 150-76-5 4-methoxy-phenol 
• 99430-02-1 4-methoxyphenyl 2,3-dibromo-3-phenylpropanoate 
• 102-92-1 Cinnamoyl chloride 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 1101612-92-3 C₂₁H₂₂O₅ 
• 18288-07-8 3-(2-hydroxy-5-methoxyphenyl)-1-phenyl-2-propene-1-one 
• 99430-03-2 2'-hydroxy-5'-methoxychalcone 
• 3262-89-3 triphenylboroxine 
• 59887-88-6 6-methoxy-chromen-4-one 

Downstream Products

• 26964-24-9 6-methoxyflavone 
• 93176-00-2 3-Hydroxy-6-methoxyflavone 
• 3033-90-7 (E)-1-(2-hydroxy-5-methoxyphenyl)-3-phenylprop-2-en-1-one 
• 75595-96-9 (2S,3R)-3-Chloro-6-methoxy-2-phenyl-chroman-4-one 
• 71993-26-5 3,3-Dichloro-6-methoxy-2-phenyl-chroman-4-one 
• 1431952-43-0 3-ferrocenylmethylidenyl-6-methoxy-2-phenylchroman-4-one 
• 1266399-40-9 8-methoxy-4-phenyl-4H-benzopyran[4,3-d][1,2,3]selenadiazole 
• 1266399-51-2 C₁₇H₁₇N₃O₃ 
• 190831-06-2 6-methoxy-2-phenylchroman-4-one 
• 1175542-34-3 8-methoxy-4-phenyl-1,4-dihydrochromeno[4,3-d][1,2,3]triazole 
• 6665-83-4 6-hydroxyflavone 
• 4250-77-5 6-hydroxyflavanone 
• 1228118-69-1 (-)-(S)-6,4'-dihydroxyflavanone 
• 1289081-28-2 6-propionoxyflavanone 

Relevant academic research and scientific papers

Preparation of a novel bridged bis(β-cyclodextrin) chiral stationary phase by thiol-ene click chemistry for enhanced enantioseparation in HPLC

A bridged bis(β-cyclodextrin) ligand was firstly synthesized via a thiol-ene click chemistry reaction between allyl-ureido-β-cyclodextrin and 4-4′-thiobisthiophenol, which was then bonded onto a 5 μm spherical silica gel to obtain a novel bridged bis(β-cyclodextrin) chiral stationary phase (HTCDP). The structures of HTCDP and the bridged bis(β-cyclodextrin) ligand were characterized by the 1H nuclear magnetic resonance (1H NMR), solid state 13C nuclear magnetic resonance (13C NMR) spectra spectrum, scanning electron microscope, elemental analysis, mass spectrometry, infrared spectrometry and thermogravimetric analysis. The performance of HTCDP in enantioseparation was systematically examined by separating 21 chiral compounds, including 8 flavanones, 8 triazole pesticides and 5 other common chiral drugs (benzoin, praziquantel, 1-1′-bi-2-naphthol, Tr?ger's base and bicalutamide) in the reversed-phase chromatographic mode. By optimizing the chromatographic conditions such as formic acid content, mobile phase composition, pH values and column temperature, 19 analytes were completely separated with high resolution (1.50-4.48), in which the enantiomeric resolution of silymarin, 4-hydroxyflavanone, 2-hydroxyflavanone and flavanone were up to 4.34, 4.48, 3.89 and 3.06 within 35 min, respectively. Compared to the native β-CD chiral stationary phase (CDCSP), HTCDP had superior enantiomer separation and chiral recognition abilities. For example, HTCDP completely separated 5 other common chiral drugs, 2 flavanones and 3 triazole pesticides that CDCSP failed to separate. Unlike CDCSP, which has a small cavity (0.65 nm), the two cavities in HTCDP joined by the aryl connector could synergistically accommodate relatively bulky chiral analytes. Thus, HTCDP may have a broader prospect in enantiomeric separation, analysis and detection. This journal is

Synthesis of Flavanone and Quinazolinone Derivatives from the Ruthenium-Catalyzed Deaminative Coupling Reaction of 2′-Hydroxyaryl Ketones and 2-Aminobenzamides with Simple Amines

The cationic Ru–H complex [(C6H6)(PCy3)(CO)RuH]+BF4– (1) with 3,4,5,6-tetrachloro-1,2-benzoquinone (L1) was found to be a highly effective catalyst for the deaminative coupling reaction of 2′-hydroxyaryl ketones with simple amines to form 3-substituted flavanone products. The analogous deaminative coupling reaction of 2-aminobenzamides with branched amines directly formed 3,3-disubstituted quinazolinone products. The catalytic method efficiently installs synthetically useful flavanone and quinazolinone core structures without employing any reactive reagents.

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.

Preparation and evaluation of a triazole-bridged bis(β-cyclodextrin)–bonded chiral stationary phase for HPLC

A triazole-bridged bis(β-cyclodextrin) was synthesized via a high-yield Click Chemistry reaction between 6-azido-β-cyclodextrin and 6-propynylamino-β-cyclodextrin, and then it was bonded onto ordered silica gel SBA-15 to obtain a novel triazole-bridged bis (β-cyclodextrin)–bonded chiral stationary phase (TBCDP). The structures of the bridged cyclodextrin and TBCDP were characterized by the infrared spectroscopy, mass spectrometry, elemental analysis, and thermogravimetric analysis. The chiral performance of TBCDP was evaluated by using chiral pesticides and drugs as probes including triazoles, flavanones, dansyl amino acids and β-blockers. Some effects of the composition in mobile phase and pH value on the enantioseparations were investigated in different modes. The nine triazoles, eight flavanones, and eight dansyl amino acids were successfully resolved on TBCDP under the reversed phase with the resolutions of hexaconazole, 2′-hydroxyflavanone, and dansyl-DL-tyrosine, which were 2.49, 5.40, and 3.25 within 30 minutes, respectively. The ten β-blockers were also separated under the polar organic mode with the resolution of arotinolol reached 1.71. Some related separation mechanisms were discussed preliminary. Compared with the native cyclodextrin stationary phase (CDSP), TBCDP has higher enantioselectivity to separate more analytes, which benefited from the synergistic inclusion ability of the two adjacent cavities and bridging linker of TBCDP, thereby enabling it a promising prospect in chiral drugs and food analysis.

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.

Flavanone-based fluorophores with aggregation-induced emission enhancement characteristics for mitochondria-imaging and zebrafish-imaging

Fluorophores with aggregation-induced emission enhancement (AIEE) characteristics applied in bioimaging have attracted more and more attention in recent years. In this work, a series of flavanone compounds with AIEE characteristics was developed and applied to fluorescence imaging of mitochondria and zebrafish. The compounds were readily prepared by the thermal dehydration of chalcone that was obtained by the reaction of o-hydroxyacetophenone and benzaldehyde. Two of these compounds showed significant AIEE characteristics by fluorescence performance experiments, including optical spectra, fluorescence spectra, fluorescence quantum yield (?F), fluorescence lifetime, and scanning electron microscopy (SEM). Compared with traditional organic fluorescent dyes, these compounds have high fluorescence emission and high fluorescence quantum yield in solid or aggregated state, which overcomes the shortcoming of aggregation-caused quenching (ACQ). More importantly, the two compounds exhibited low cytotoxicity and good cytocompatibility in A549 lung cells at the experimental concentration range and they specifically targeted mitochondria, which make it of great potential use in mitochondria labeling. In addition, they were embryonic membrane permeable and had different affinities for different tissues and organs of zebrafish, but mainly distributed in the digestive system, providing a basis for the application of such compounds in bioimaging. These AIEE compounds with superior properties could be of great potential use in mitochondria imaging and other in vivo studies.

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.

A cationic cyclodextrin clicked bilayer chiral stationary phase for versatile chiral separation in HPLC

A cationic cyclodextrin (CD) clicked bilayer chiral stationary phase (CSP) was developed via click chemistry for chiral separations in multimode high-performance chromatography (HPLC). The versatility of this new CSP was evaluated using 17 model racemic pairs including aromatic alcohols, flavonoids and isoxazoline enantiomers in both reversed-phase (RP) and normal-phase (NP) HPLC. The CD functionality-enhanced chiral selectivity was elucidated in different elution modes. Higher chiral resolutions were shown in the RP-elution mode due to the inclusion complexation in comparison to the NP-elution mode. The highest chiral resolution of 4.40 was achieved for 4ClPh-OPr, with 12 racemic pairs baseline separated in RP-HPLC. The addition of organic modifiers in mobile phases plays an important role in optimizing the enantioselectivities of the cationic CD bilayer CSP in NP-HPLC.

Functionalities tuned enantioselectivity of phenylcarbamate cyclodextrin clicked chiral stationary phases in HPLC

The mixed chloro- and methyl- functionalities can greatly modulate the enantioselectivities of phenylcarbamate cyclodextrin (CD) clicked chiral stationary phases (CSPs). A comparison study is herein reported for per(4-chloro-3-methyl)phenylcarbamate and per(2-chloro-5-methyl)phenylcarbamate β-CD clicked CSPs (i.e., CCC4M3-CSP and CCC2M5-CSP). The enantioselectivity dependence on column temperature was studied in both normal-phase and reversed-phase mode high performance liquid chromatography (HPLC). The thermodynamic study revealed that the stronger intermolecular interactions can be formed between CCC4M3-CSP and chiral solutes to drive the chiral separation. The higher enantioselectivities of CCC4M3-CSP were further demonstrated with the enantioseparation of 17 model racemates in HPLC.