1220531-63-4

Upstream product

• 1218-22-0 3-phenyl-1-(2'-hydroxy-5'-bromophenyl)-2-propen-1-one 
• 39729-11-8 2'-hydroxychalcone dibromides 
• 7726-95-6 bromine 
• 108-24-7 acetic anhydride 
• 487-26-3 Flavanone 
• 536-74-3 phenylacetylene 
• 1761-61-1 5-bromosalicyclaldehyde 
• 102-92-1 Cinnamoyl chloride 
• 140-10-3 (E)-3-phenylacrylic acid 
• 1218-22-0 (E)-1-(5-bromo-2-hydroxyphenyl)-3-phenylprop-2-en-1-one 
• 1450-75-5 5-Bromo-2-hydroxyacetophenone 
• 100-52-7 benzaldehyde 
• 51483-92-2 6-bromo-1-benzopyran-4(4H)-one 
• 98-80-6 phenylboronic acid 

Downstream Products

• 1218-80-0 6-bromoflavone 
• 1222-12-4 6-bromo-3-hydroxy-2-phenyl-4H-chromen-4-one 
• 107917-81-7 3,6-dibromo-Flavone 
• 78115-52-3 6-Bromo-3-methylene-2-phenyl-chroman-4-one 

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.

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.

Fast and efficient synthesis of flavanones from cinnamic acids

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl2. The acid chlorides were then treated with substituted phenols in BF3· OEt2to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

Ecofriendly synthesis of halogenated flavonoids and evaluation of their antifungal activity

Brominated and chlorinated flavonoids belonging to different classes (flavanones, flavones and catechins) were prepared from the corresponding flavonoids by a simple and ecofriendly procedure based on the use of sodium halides, aqueous hydrogen peroxide and acetic acid. Pure samples of substrates and products were tested against Trichoderma koningii, Fusarium oxysporum and Cladosporium cladosporioides, common saprotrophic soil and seed fungi, potential pathogens for humans and their activity was expressed as linear mycelial growth inhibition (%). Among them, 8-chloro-5,7,3′,4′-tetramethoxyepicatechin 29, a novel catechin derivative, exhibited a remarkable effect against all tested fungi also at low concentrations.

Simple and efficient one step synthesis of functionalized flavanones and chalcones

A facile and highly efficient microwave-assisted synthesis of functionalized chalcones and flavanones based on the Claisen-Schmidt condensation reaction is reported. The method describes the synthesis of flavanones in single step with excellent yield and it was revealed that position and number of substituents on acetophenones and aromatic aldehydes played a very crucial and key role in the construction of flavanone derivatives. Among the thirty two synthesized compounds, five chalcones and one flavanone were novel compounds.

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.

Efficient synthesis of polyoxygenated flavones from naturally occurring flavanones

Flavonoids are constituents of the human diet (they are present in many beverages and food), and in organisms they are responsible for several biological functions, including that of antioxidant. Because of the increasing interest in these molecules, methods for their synthesis and structural modification are of great importance; studies on the biological activities of many of these compounds are insufficient because of their scarcity and/or high cost. We have developed an expeditious synthesis of polyoxygenated flavones, starting from available and inexpensive flavanones, using a bromination- methoxylation procedure. A series of flavonoids that are not otherwise accessible can be prepared using this method. As an example, 3′-demethoxysudachitin, a limited flavone possessing antimicrobial activity against methicillin-resistant Staphylococcus aureus and Helicobacter pylori and acting as a 2,2-diphenyl-1-picrylhydrazyl (DPPH) scavenger, was prepared in fairly satisfactory yield.

Selective halogenation of flavanones

A mild, efficient and regioselective method for the selective halogenation of flavonoids is presented. Halogenated flavanones and flavones are considered potential benzodiazepine receptor ligands and with DMD/NaX or oxone/acetone/water/NaX systems they can be synthesised in preparative amounts.

Pyrolitic Elimination of Hydrogen Halide and Halogen from 2,3-Dihalogenoketones

The thermal elimination of hydrogen chloride from 2'-hydroxychalcone dichlorides occured in two stages, initially forming 3-chloroflavones and then flavones; α-chloro-2'-hydroxychalcones, the likely intermediates in the formation of 3-chloroflavones, also yielded the same products.The pyrolysis of 2'-hydroxychalcone dibromides resulted in debromination as well as dehydrobromination with the consequent appearence of brominated flavones among the products.The formation of 3-bromoflavones was not observed but the isomeric (E)-α-bromo-2'-hydroxychalcones thermally isomerized to their (Z)-isomers and then underwent cyclization and dehydrobromination.The bromide were considerably more reactive than the dichlorides but, as a synthetic procedure, the pyrolysis of the dichlorides is cleaner and more productive.