57060-61-4

Basic information

• Product Name: Aurone
• Synonyms: (Z)-2-benzylidene-4,6-diMethoxybenzofuran-3(2H)-one
• CAS NO: 57060-61-4
• Molecular Formula: C₁₇H₁₄O₄
• Molecular Weight: 282.29066
• Mol File: 57060-61-4.mol

Chemical Properties

• Appearance: /
• CAS DataBase Reference: Aurone(CAS DataBase Reference)
• NIST Chemistry Reference: Aurone(57060-61-4)
• EPA Substance Registry System: Aurone(57060-61-4)

Safety Data

• Hazardous Substances Data: 57060-61-4(Hazardous Substances Data)

Upstream product

• 536-74-3 phenylacetylene 
• 570-02-5 2,4,6-trimethoxybenzoic acid 
• 135746-18-8 2-(Hydroxy-phenyl-methyl)-4,6-dimethoxy-benzofuran-3-one 
• 67-56-1 methanol 
• 623-11-0 1-methyl-4-nitrosobenzene 
• 1775-97-9 flavokawain B 
• 7722-84-1 dihydrogen peroxide 
• 103040-51-3 2-chloro-1-(2-hydroxy-4,6-dimethoxyphenyl)ethanone 
• 100-52-7 benzaldehyde 
• 90-24-4 2-hydroxy-4,6-dimethoxyacetophenone 
• 131968-26-8 Acetic acid 2-((Z)-2-bromo-3-phenyl-acryloyl)-3,5-dimethoxy-phenyl ester 
• 54930-58-4 2'-acetoxy-4',6'-dimethoxychalcone dibromide 
• 54930-59-5 2'-hydroxy-4',6'-dimethoxychalcone dibromide 
• 57060-50-1 trans-α-Bromo-2'-hydroxy-4',6'-dimethoxychalcon 

Downstream Products

• 31022-84-1 trans-2-benzylidene-4,6-dimethoxy-2H-benzofuran-3-one epoxide 
• 38216-53-4 (Z)-2-benzylidene-4,6-dihydroxybenzofuran-3(2H)-one 
• 95280-40-3 2-benzyl-4,6-dimethoxybenzofuran-3(2H)-one 

Relevant articles and documents

Metal-free methodology for the preparation of sterically hindered alkynoylphenols and its application to the synthesis of flavones and aurones

A metal-free synthesis for the preparation of sterically demanding ortho-demethylated ynones from mixed anhydrides and potassium alkynyltrifluoroborate salts has been developed. The one-pot reaction proceeds rapidly in the presence of a Lewis acid without the exclusion of air and moisture. This method is advantageous in that it is operationally simple, proceeds under mild conditions, and has a broad substrate scope. 2,6-Dimethoxy substituted anhydrides afford the corresponding mono-demethylated ynone products in good yields. In particular, 2-hydroxy substituted ynone products are valuable synthetic intermediates because their conversion to biologically active natural product scaffolds is straightforward. Flavones were obtained via 6-endo cyclization of the o-alkynyoylphenol intermediates under acidic conditions. Cesium carbonate was found to promote rapid 5-exo cyclization to furnish aurone products.

Aurones as histone deacetylase inhibitors: Identification of key features

In this study, a total of 22 flavonoids were tested for their HDAC inhibitory activity using fluorimetric and BRET-based assays. Four aurones were found to be active in both assays and showed IC50 values below 20 μM in the enzymatic assay. Molecular modelling revealed that the presence of hydroxyl groups was responsible for good compound orientation within the isoenzyme catalytic site and zinc chelation.

In vitro inhibitory properties of ferrocene-substituted chalcones and aurones on bacterial and human cell cultures

Two series of ten chalcones and ten aurones, where ferrocene replaces the C ring and with diverse substituents on the A ring were synthesized. The compounds were tested against two antibiotic-sensitive bacterial strains, E. coli ATCC 25922 and S. aureus ATCC 25923, and two antibiotic-resistant strains, S. aureus SA-1199B and S. epidermidis IPF896. The unsubstituted compound and those with methoxy substitution showed an inhibitory effect on all bacterial strains at minimum inhibitory concentrations ranging between 2 and 32 mg L -1. For four of these compounds, the effect was bactericidal, as opposed to bacteriostatic. The corresponding organic aurones did not show growth inhibition, underscoring the role of the ferrocene group. The methoxy-substituted aurones and the unsubstituted aurone also showed low micromolar (IC50) activity against MRC-5 non-tumoral lung cells and MDA-MB-231 breast cancer cells, suggesting non-specific toxicity.

Discovery of naturally occurring aurones that are potent allosteric inhibitors of hepatitis C virus RNA-dependent RNA polymerase

We have identified naturally occurring 2-benzylidenebenzofuran-3-ones (aurones) as new templates for non-nucleoside hepatitis C virus (HCV) RNA-dependent RNA polymerase (RdRp) inhibitors. The aurone target site, identified by site-directed mutagenesis, is located in thumb pocket I of HCV RdRp. The RdRp inhibitory activity of 42 aurones was rationally explored in an enzyme assay. Molecular docking studies were used to determine how aurones bind to HCV RdRp and to predict their range of inhibitory activity. Seven aurone derivatives were found to have potent inhibitory effects on HCV RdRp, with IC50 below 5 μM and excellent selectivity index (inhibition activity versus cellular cytotoxicity). The most active aurone analogue was (Z)-2-((1-butyl-1H-indol-3-yl)methylene)-4,6-dihydroxybenzofuran-3(2H)-one (compound 51), with an IC50 of 2.2 μM. Their potent RdRp inhibitory activity and their low toxicity make these molecules attractive candidates as direct-acting anti-HCV agents.

Reactions of carbanions with 1,3-benzodioxin-4-ones: Facile routes to flavones, aurones, and acyl phloroglucinols

Two 1,3-benzodioxin-4-ones react with enolates, acetylides and aryllithium reagents to afford adducts that were converted into flavones, aurones, and an acyl phloroglucinol. Georg Thieme Verlag Stuttgart.

Oxidative rearrangement of 2′-hydroxychalcones having no substituent at the 3′- and 5′-positions with thallium(III) nitrate in methanol

Oxidation of 2′-hydroxychalcones with no substituents at the 3′- and 5′-positions with thallium(III) nitrate (TTN) in methanol has been studied in detail and the following results obtained. (1) 2′-Hydroxy-4,6′-dimethoxychalcones (1b and 2b) have increased

Kinetics and Mechanism of the Cyclisation of Some 2'-Hydroxychalcone Epoxides and Subsequent Elimination Reactions of Aurone Hydrates

Analysis of the pH-rate profile for the cyclisation of the monoanion of 2'-hydroxychalcone epoxide which gives 3-hydroxyflavanone and of some 6'-alkoxy-substituted analogues which give mostly aurone hydrate, gives rate coefficients which quantify the preference for α over β cyclisation when 6'-substituents are present.These are considered in terms of stereoelectronic factors which may be responsible for the preference.Also reported are rate coefficients for the subsequent reaction of aurone hydrates in which aurones and coumaranones are formed.

Amine-effected cyclization of chalcone dihalides to aurones

The possibility of employing the amine-catalysed cyclization of αβ-dibromodihydrochalcones and α-bromochalcones as a general synthesis of aurones was studied using cyclohexylamine and the most representative member of each class of these αβ-disubstituted ketones and α-halogeno chalcones. Overall yields of heterocyclic products were generally poor except from 4′6′-dimethoxy- and 3-nitro-substituted chalcone systems; aurones were obtained in fair yield from the former and in excellent yield from the latter. 22′-Diacetoxychalcone dibromide and 22′-diacetoxy-α-bromochalcone cyclised to a 2-benzoylbenzofuran to the exclusion of the corresponding aurone and flavone.

Regioselective synthesis of 2-arylidene coumaran-3-ones by dye-sensitized photooxygenation of 2-hydroxyphenyl-styrylketones in the presence of sodium dodecyl sulphate

2′-Hydroxyphenylstyrylketones when subjected to dye- sensitized photooxygenation in the presence of sodium dodecylsulphate (8x × 10-3M) in methanol, yielded the corresponding oxidatively cyclized products, i.e., 2-aryl idenecoumaran 3-ones and

Synthesis of 2-Benzylidene-3(2H)-benzofuran-3-ones (Aurones) by Oxidation of 2'-Hydroxychalcones with Mercury(II) Acetate

The reaction of 2'-hydroxychalcones with mercury(II) acetate in acetic acid gives predominantly 2-benzylidene-3(2H)-benzofuran-3-ones (aurones) in 28-62 percent yield accompanied by flavonones in 5-21 percent yield.