36685-41-3

Upstream product

• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 123-11-5 4-methoxy-benzaldehyde 
• 110-89-4 piperidine 
• 67139-32-6 trans-3-mesyloxy-4'-methoxyflavanone 
• 16619-68-4 1-(2-hydroxyphenyl)-3-phenylprop-2-yn-1-one 
• 93868-47-4 2'-acetoxy-4-methoxychalcone dibromide 
• 101278-20-0 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)prop-2-yn-1-one 
• 131968-27-9 Acetic acid 2-[(Z)-2-bromo-3-(4-methoxy-phenyl)-acryloyl]-phenyl ester 
• 67139-31-5 trans-3-mesyloxyflavanone 
• 103-67-3 benzyl-methyl-amine 
• 109600-56-8 1-(o-hydroxyphenyl)-3-(4-methoxyphenyl)propargylic alcohol 
• 768-60-5 4-methoxyphenylacetylen 
• 201230-82-2 carbon monoxide 
• 95-56-7 2-hydroxybromobenzene 

Downstream Products

• 4143-74-2 4'-methoxyflavone 
• 876505-29-2 2-(4-methoxybenzoyl)benzofuran-3-ol 
• 860181-81-3 2-bromo-2-(α-bromo-4-methoxy-benzyl)-benzofuran-3-one 
• 141885-61-2 (2-Hydroxy-phenyl)-[4-(4-methoxy-phenyl)-2,5-diphenyl-2H-pyrazol-3-yl]-methanone 
• 75318-35-3 E-2-[(4-methoxyphenyl)methylene]benzo[b]furan-3-one 
• 142078-52-2 C₁₆H₁₂O₄ 
• 6889-78-7 4'-(methoxy)-3-hydroxyflavone 
• 590345-68-9 (6RS)-6-(4-Methoxyphenyl)-6,12-dihydro-benzofuro[2,3-c][1,5]benzothiazepin 
• 1008105-84-7 (Z)-2-(4-methoxybenzylidene)-2,3-dihydrobenzofuran-3-ol 
• 94501-18-5 p-methoxyphenyl(benzofuran-2-yl)methanol 
• 63157-19-7 (1-benzofuran-2-yl)(4-methoxyphenyl)methanone 
• 112980-31-1 (2Z)-2-[(4-hydroxyphenyl)methylidene]benzofuran-3-one 

Relevant academic research and scientific papers

AURONE DERIVATIVES AND USES THEREOF FOR CONTROLLING BACTERIA AND/OR FUNGI

The present invention relates to aurones compounds of formula (I) and their uses for controlling a bacterium and/or a fungus. The invention also relates to the use of such compounds as phytoprotective and/or decontaminating and/or disinfectant agent and compositions comprising them.

In quest of small-molecules as potent non-competitive inhibitors against influenza

A series of scaffolds namely aurones, 3-indolinones, 4-quinolones and cinnamic acid-piperazine hybrids, was designed, synthesized and investigated in vitro against influenza A/H1N1pdm09 virus. Designed molecules adopted different binding mode i.e., in 430-cavity of neuraminidase, unlike sialic acid and oseltamivir in molecular docking studies. All molecules reduced the viral titer and exhibited non-cytotoxicity along with cryo-protective property towards MDCK cells. Molecules (Z)-2-(3′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2f), (Z)-2-(4′-Chloro-benzylidene)-1,2-dihydro-indol-3-one (2g) and 2-(2′-Methoxy-phenyl)-1H-quinolin-4-one (3a) were the most interesting molecules identified in this research, endowed with robust potencies showing low-nanomolar EC50 values of 4.0 nM, 6.7 nM and 4.9 nM, respectively, compared to reference competitive and non-competitive inhibitors: oseltamivir (EC50 = 12.7 nM) and quercetin (EC50 = 0.56 μM), respectively. Besides, 2f, 2g and 3a exhibited good neuraminidase inhibitory activity in sub-micromolar range (IC50 = 0.52 μM, 3.5 μM, 1.3 μM respectively). Moreover, these molecules were determined as non-competitive inhibitors similar to reference non-competitive inhibitor quercetin unlike reference competitive inhibitor oseltamivir in kinetics studies.

METHOD FOR SYNTHESIZING (Z)-AURONE AND DERIVATIVE COMPOUNDS THEREOF

One embodiment of the present invention is described below. Provided is (Z)-operon comprising o - (alkanone -1 - yl) phenol or its derivative compound in a thallium (Tl) catalyst and an cyclization step for cyclizing the compound under an organic solvent, and a method for producing the derivative compound.

Transition-metal-free synthesis of polysubstituted pyrrole derivatives via cyclization of methyl isocyanoacetate with aurone analogues

Presented herein is an unprecedented transition-metal-free cyclization of methyl isocyanoacetate with aurone analogues catalyzed by NaOH. Various 2,3,4-trisubstituted pyrroles were obtained in excellent yields (up to 99%). The high efficiency of this synthetic procedure, coupled with the operational simplicity and atom economy, makes it an attractive method for the synthesis of polysubstituted pyrroles.

Catalytic Asymmetric [3 + 2] Cycloaddition Reaction between Aurones and Isocyanoacetates: Access to Spiropyrrolines via Silver Catalysis

The first enantioselective formal [3 + 2] cycloaddition of aurone analogues with isocyanoacetates was developed via chiral Ag-complex catalysis. A variety of optically enriched spiro-1-pyrrolines were obtained in excellent yields, diastero- and enantioselectivities (up to 99% yield, >20:1 dr, >99% ee). This synthetic approach represents an extremely simple, efficient, and atom-economical method for spiro-1-pyrrolines synthesis.

One-pot Synthesis of Aurones through Oxidation-cyclization Tandem Reaction Catalyzed by Copper Nanoparticles Catalyst

Aurones were synthesized through an oxidation-cyclization tandem reaction of 2-(1- hydroxyprop-2-ynyl)phenols catalyzed by copper nanoparticles (Cu NPs) with bipyridine as the ligand. In the reaction, oxygen worked as a green and mild oxidant to give the best results. Cu NPs were dually activated by bipyridine ligand and water, and showed highly efficient catalytic activities to the oxygen oxidation and the cylization to give aurones and flavonoids.

Unusual Olefinic C-H Functionalization of Simple Chalcones toward Aurones Enabled by the Rational Design of a Function-Integrated Heterogeneous Catalyst

Flavonoids, which are ubiquitous plant secondary metabolites obtained from chalcones, mostly possess 6-membered C-rings derived from 6-endo-trig cyclization of chalcones. However, aurones, which are a class of flavonoids that rarely occur naturally, possess unusual 5-membered C-rings biosynthesized from chalcones by mainly performing B-ring oxidation. Therefore, the chemical catalytic transformation from simple chalcones into aurones is attractive, because it overcomes the drawback of known limited enzyme catalysis. The catalytic transformation, however, has not yet been reported because of the preferential 6-membered ring formation as with the biosynthesis and the need for rare intramolecular olefinic C-H functionalization. Here, we developed the catalytic olefinic C-H functionalization of simple chalcones toward various aurones enabled by the rational design of a function-integrated heterogeneous catalyst - a Pd-on-Au bimetallic nanoparticle catalyst supported on CeO2 - using O2 in air as the sole oxidant without any additives. In this system, the four conditions that were required for the challenging transformation toward aurones were achieved by the respective components of the catalyst: (a) a supported Pd catalyst: a catalyst for the olefinic C-H functionalization of chalcones toward aurones, (b) an Au promoter: an improvement in the catalytic activity by stabilizing Pd(0), (c) a CeO2 support: the inhibition of the 6-endo-trig cyclization utilizing the adsorption of chalcones, and (d) a Pd-on-Au structure: the inhibition of Au-catalyzed flavone synthesis. This catalytic transformation will promote not only the pharmaceutical study of aurones but also the rational design of a heterogeneous catalyst for the development of organic reactions that are not yet realized by homogeneous catalysts or biocatalyst.