1220893-39-9

Upstream product

• 100-52-7 benzaldehyde 
• 88034-35-9 pentacarbonyl{1-(1-methoxy-3(E)-phenyl-2-propenylidene)}chromium⁽⁰⁾ 
• 2713-29-3 2-iodo-4-fluorophenol 
• 85169-02-4 3-(4-fluoro-phenoxy)propionitrile 
• 66892-34-0 6-fluoro-4-chromanone 
• 98-80-6 phenylboronic acid 
• 371-41-5 4-Fluorophenol 
• 347-54-6 5-fluoro-2-hydroxybenzaldehyde 
• 536-74-3 phenylacetylene 
• 3262-89-3 triphenylboroxine 
• 105300-38-7 6-fluoro-4H-chromen-4-one 
• 394-32-1 1-(5-fluoro-2-hydroxyphenyl)ethan-1-one 
• 1431-92-1 (E)-1-(2-hydroxy-5-fluorophenyl)-3-phenylprop-2-en-1-one 
• 1431-92-1 5′-fluoro-2′-hydroxychalcone 

Downstream Products

• 111502-77-3 ((2S,4R)-6-Fluoro-4-hydroxy-2-phenyl-chroman-4-yl)-acetic acid ethyl ester 
• 75595-41-4 3-Chloro-6-fluoro-2-phenyl-chromen-4-one 
• 75595-38-9 3,3-Dichloro-6-fluoro-2-phenyl-chroman-4-one 
• 98769-88-1 4-chloro-6-fluoro-3-formyl-flav-3-ene 
• 99110-95-9 3-N,N-dimethylaminomethylidene-6-fluoro-flavanone 
• 1266399-35-2 8-fluoro-4-phenyl-4H-benzopyran[4,3-d][1,2,3]selenadiazole 
• 364-57-8 6-fluoro-3-hydroxy-2-phenyl-4H-chromen-4-one 
• 1431-92-1 (E)-1-(2-hydroxy-5-fluorophenyl)-3-phenylprop-2-en-1-one 
• 111502-91-1 ((2S,4R)-6-Fluoro-4-hydroxy-2-phenyl-chroman-4-yl)-acetic acid 

Relevant academic research and scientific papers

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.

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.

Palladium-Catalyzed [3+3] Annulation of Vinyl Chromium(0) Carbene Complexes through Carbene Migratory Insertion/Tsuji–Trost Reaction

Vinyl chromium(0) Fischer carbene complexes were employed as the source of π-allylic palladium species for catalytic [3+3] annulation under palladium catalysis. Mechanistically, this transformation is proposed to involve carbene migratory insertion and intramolecular Tsuji–Trost reaction as the key steps. Substituted six-membered heterocyclic flavonones and quinolines are obtained, depending on the nucleophilic functional group on the coupling partners.

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.

Impact of mono- and disubstitution on the colorimetric dynamic covalent switching chalcone/flavanone scaffold

The effect of aryl substitution on various aspects of the interconversion of ortho-hydroxychalcones and flavanones has been studied using multiple spectroscopic techniques. Derivatization of the core scaffold predictably alters the midpoint pH of this equilibration process suggesting its viability for application as a functional colorimetric molecular switch.

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.

Exploration on asymmetric synthesis of flavanone catalyzed by (S)-pyrrolidinyl tetrazole

An improved method of the synthesis of flavanones catalyzed by pyrrolidine and BF3·Et2O has been developed and a lot of flavanones could be easily synthesized via this method. The asymmetric synthesis of flavanone from benzaldehyde a

Synthesis and cytotoxic activity of 4-aryl-4H-chromeno[4,3-d] [1,2,3] selenadiazoles

Fourteen 4-Aryl-4H-chromeno[4,3-d][1,2,3] selenadiazole derivatives were synthesized by the reaction of fla-vonone-4-semicarbazones with SeO2. The structures of the target compounds 1a-n were elucidated by 1H NMR, IR spectra, ESI-MS and elemental analyses. The preliminary cytotoxic activities of 1a-n against K562, KB, A549, SMC-7721 and SGC-7901 cell lines were evaluated by MTT method, indicating that most compounds displayed moderate to good antiproliferative activities against K562 and KB cell lines. Compounds 1m and 1n, the most potent ones, were promising template for development of novel potent antitumor agents.

An improved method for the synthesis of flavanones

An isomerization of 2′-hydroxychalcones into the corresponding flavanones in ethanol in the presence of triethylamine is described.