126443-18-3

Upstream product

• 1122-91-4 4-bromo-benzaldehyde 
• 100-06-1 1-(4-methoxyphenyl)ethanone 
• 27465-66-3 4-bromocinnamoyl chloride 
• 33397-21-6 tris(4-methoxyphenyl)bismuth 
• 106-37-6 1.4-dibromobenzene 
• 7448-86-4 1-(4-methoxyphenyl)prop-2-en-1-one 
• 20912-79-2 4-methoxyphenacylidene dimethylsulphurane 
• 19350-68-6 p-bromobenzaldehyde tosylhydrazone 

Downstream Products

• 1021493-95-7 3-(4-bromophenyl)-1-(4-methoxyphenyl)-4-nitrobutan-1-one 
• 160210-32-2 (2E)-3-(4-hydroxyphenyl)-1-(4-methoxyphenyl)prop-2-en-1-one 

Relevant academic research and scientific papers

Novel solid-supported dimerization-heteroannulation of chalcones: simple and efficient synthesis of 2,4,6-triaryl-3-methylarylpyridines

2,4,6-Triaryl-3-methylarylpyridines were obtained, in 60-70% yield, by a novel one-pot solventless solid-supported dimerization-heteroannulation reaction of chalcones and compounds possessing terminal -CONH2 functionality, at 125-135 °C, using immobilized Bi(III) nitrate and Zn(II) chloride as co-catalyst. Initially, chalcones were prepared, in nearly quantitative yield, by a modified aldol condensation, in neutral aqueous medium, in the presence of p-toluenesodium sulfonate.

Antimicrobial activity of xanthohumol and its selected structural analogues

The objective of this study was to evaluate the antimicrobial activity of structural analogues of xanthohumol 1, a flavonoid compound found in hops (Humulus lupulus). The agar-diffusion method using filter paper disks was applied. Biological tests performed for selected strains of Gram-positive (Staphylococcus aureus) and Gram-negative (Escherichia coli) bacteria, fungi (Alternaria sp.), and yeasts (Rhodotorula rubra, Candida albicans) revealed that compounds with at least one hydroxyl group - all of them have it at the C-4 position - demonstrated good activity. Our research showed that the strain S. aureus was more sensitive to chalcones than to the isomers in which the heterocyclic ring C is closed (flavanones). The strain R. rubra was moderately sensitive to only one compound: 4-hydroxy-4′-methoxychalcone 8. Loss of the hydroxyl group in the B-ring of 4′-methoxychalcones or its replacement by a halogen atom (-Cl, -Br), nitro group (-NO2), ethoxy group (-OCH2CH3), or aliphatic substituent (-CH3, -CH2CH3) resulted in the loss of antimicrobial activity towards both R. rubra yeast and S. aureus bacteria. Xanthohumol 1, naringenin 5, and chalconaringenin 7 inhibited growth of S. aureus, whereas 4-hydroxy-4′-methoxychalcone 8 was active towards two strains: S. aureus and R. rubra.

Monoamine oxidase inhibitory activity of methoxy-substituted chalcones

The MAO-B inhibitory activity of chalcone (1, 3- diphenyl-2-propen-1-one) based compounds arise from its structural similarity with 1, 4-diphenyl-2-butene, a known MAO-B inhibitor. Based on our previous report, the methoxy-substituted with fluorine containing chalcones are promising reversible MAO-B inhibitors, while in the present study, a series of methoxylated chalcones (C1-C9) bearing substitution on the para position of ring B was synthesized and evaluated for their human monoamine oxidase inhibitory activity. With the exception of (2E)-1-(4-methoxyphenyl)-3-(4-nitrophenyl) prop-2-en-1-one (C7), which is a nonselective inhibitor, the chalcones exhibited competitive, selective, and reversible inhibition of hMAO-B. The most potent compound, (2E)-3-[4-(dimethylamino) phenyl]-1-(4-methoxyphenyl) prop-2-en-1-one (C5), showed the best inhibitory activity towards hMAO-B (IC50 = 0.29 ± 0.011 μM; Ki = 0.14 ± 0.001 μM). The reversibility of MAO-B inhibition by compound C5 was demonstrated by the recovery of enzyme activity after dialysis of mixtures containing enzyme and inhibitor. The reversiblity of C5 was 25.38 ± 1.40 and 92.00 ± 3.87% before and after dialysis, respectively. PAMPA was carried out to evaluate the blood-brain barrier effects of the designated compounds. Moreover, the most potent MAO-B inhibitor, C5, was found to be nontoxic towards cultured hepatic cells at 5 and 25 μM, with 97 and 90% viability. Molecular docking study was performed against hMAO-B to observe the binding site interactions of the lead compound.

Chalcones and bis-chalcones analogs as DPPH and ABTS radical scavengers

Background: A number of synthetic scaffolds, along with natural products, have been identified as potent antioxidants. The present study deals with the evaluation of varyingly substituted, medicinally distinct class of compounds “chalcones and bis-chalcon

Alkene Synthesis by Photo-Wolff-Kischner Reaction of Sulfur Ylides and N-Tosylhydrazones

A visible-light-driven and room temperature photo-Wolff-Kischner reaction of sulfur ylides and N-tosylhydrazones has been developed for the first time to provide modular access to alkene synthesis. The high functional group tolerance and broad substrate scope were demonstrated by more than 60 examples. Both E- and Z-olefinic stereochemistry in the products could be controlled with excellent stereoselectivity. A series of mechanistic studies support that the reaction should proceed through a radical-carbanion crossover pathway, specifically involving addition of photo-generated sulfur ylide radical cations to N-tosylhydrazones to form carbanions and subsequent Wolff-Kischner process.

Method using Ti (III) complex catalytic alkyne selective hydrogenation reduction to prepare chalcone compounds

The invention discloses a method for preparing chalcone compounds through selective hydrogenation of Ti (III) complexes to prepare chalcone compounds, wherein zinc powder is used as a catalyst, zinc powder is a reducing agent, triethylamine hydrochloride is a proton source, and an alkyne and triethylamine hydrochloride are subjected to radical selective addition reaction under the protection of inert gas to generate chalcone compounds. The reaction condition is mild, the operation is simple, the reaction time is short, the reaction product is single, the atom economy is high, and only the product needs to be separated by simple column chromatography after the reaction is finished. The chalcone compound has wide biological activity and medicinal value.

Aza-BODIPY Platform: Toward an Efficient Water-Soluble Bimodal Imaging Probe for MRI and Near-Infrared Fluorescence

In this study, an original aza-BODIPY system comprising two Gd3+ complexes has been designed and synthesized for magnetic resonance imaging/optical imaging applications, by functionalization of the boron center. This strategy enabled the obtain

Synthesis of 3-fluoro-2,5-disubstituted furans through ring expansion ofgem-difluorocyclopropyl ketones

The synthesis of 3-fluoro-2,5-disubstituted furans fromgem-difluorocyclopropyl ketones was accomplished using trifluoromethanesulfonic acid (CF3SO3H) through ring expansion owing to the activation of the carbonyl group in the starting material. The present synthesis of 3-fluorofurans tolerates substrates designed for products with aromatic substituents at the C-2 and C-5 positions.

An Easy Access to Oxime Ethers by Pd-Catalyzed C—O Cross-Coupling of Activated Aryl Bromides with Ketoximes and Chalcone Oximes

An efficient Pd-catalyzed method for C—O cross-coupling of ketoximes and chalcone oximes with activated aryl bromides and bromo-chalcones has been developed. All oxime ethers were obtained in good to excellent yields by [(π-allyl)PdCl]2/tBuXPhos (L7) catalyst system. TrixiePhos (L11) was also found to be effective for the oxime coupling. This method offers an easy and smooth coupling of chalcone oximes with activated aryl bromides and bromo-chalcones, which has not been previously explored.

Palladium anchored on guanidine-terminated magnetic dendrimer (G3-Gu-Pd): An efficient nano-sized catalyst for phosphorous-free Mizoroki-Heck and copper-free Sonogashira couplings in water

In this research, a novel type of Fe3O4&at;silica-supported dendrimer capped by guanidine groups for immobilization of palladium was reported. This novel nano-sized catalyst was characterized by FTIR, TGA, XRD, FESEM, EDX, VSM, XPS and HRTEM methods. Enhanced catalytic activity of the prepared catalyst in Mizoroki-Heck and copper-free Sonogashira coupling reactions were evaluated in water as a green solvent. The influence of the various reaction parameters such as catalyst dosage, time and temperature on two mentioned C–C coupling reactions were studied. Results showed that the catalyst could be easily recovered by simple separation by an external magnet and reused for five cycles of recovery without considerable losing of its activity.