75318-36-4

Upstream product

• 66406-62-0 2'-hydroxy-4-nitrochalcone dibromide 
• 66406-69-7 (Z)-2'-Acetoxy-α-brom-4-nitrochalcon 
• 38216-51-2 (Z)-2-(4-nitrobenzylidene)benzofuran-3(2H)-one 
• 38270-09-6 1-(2-hydroxyphenyl)-3-(4-nitrophenyl)prop-2-en-1-one 
• 118-93-4 o-hydroxyacetophenone 
• 555-16-8 4-nitrobenzaldehdye 
• 2491-36-3 2-(2-bromoacetyl)hydroxybenzene 
• 38270-09-6 (E)-2'-hydroxy-4-nitrochalcone 
• 67139-34-8 Methanesulfonic acid (2R,3R)-2-(4-nitro-phenyl)-4-oxo-chroman-3-yl ester 
• 66406-61-9 4-Nitro-2'-acetoxy-chalkondibromid 
• 66406-67-5 (Z)-α-bromo-2'-hydroxy-4-nitrochalcone 
• 66406-66-4 (E)-α-bromo-2'-hydroxy-4-nitrochalcone 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 

Downstream Products

• 141885-62-3 (2-Hydroxy-phenyl)-[4-(4-nitro-phenyl)-2,5-diphenyl-2H-pyrazol-3-yl]-methanone 

Relevant academic research and scientific papers

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.

An unusual triazole synthesis from aurones

Attempts to prepare azido-substituted aurones via a copper-catalyzed azidation failed to afford the desired product, but instead resulted in an unusual triazole formation reaction. Further efforts noted that copper was not required for this reaction, but simply thermal treatment with sodium azide in a polar aprotic solvent. A wide range of substitution patterns were tolerated in this reaction to afford the interesting salicyl-substituted triazoles in modest to excellent yield. While the mechanism is not yet clear, a simple elimination/cyclization pathway seems unlikely given the failure of the reaction on the corresponding thioaurones, which feature an even better thiol leaving group. Regardless, the potential utility of these easily accessible, multifunctional compounds should engender further interest and applications.

"On water" synthesis of aurones: First synthesis of 4,5,3',4',5'-pentamethoxy-6-hydroxyaurone from Smilax riparia

A simple and green method for the synthesis of aurones by condensation of benzofuranone with aromatic aldehyde in neat water has been developed. The main advantages of this protocol include good yields, absence of catalyst, reagent, organic solvent, work-up and chromatographic purification. 4,5,3',4',5'-Pentamethoxy-6-hydroxyaurone, isolated from Smilax riparia was synthesized for the first time from 3-benzyloxy-4,5-dimethoxybenzaldehyde in five steps. {figure presented}.

Rapid synthesis of aurones under mild conditions using a combination of microwaves and deep eutectic solvents

The combination of microwave heating and the deep eutectic solvent formed from choline chloride and urea has resulted in a new, essentially neutral, yet rapid method for the synthesis of a wide range of aurone derivatives. While isolated yields remain somewhat variable, in virtually every case, a significant increase in yield has been observed on going from conventional thermal heating to microwave heating. In addition, some compounds inaccessible using prior methods have become reproducibly available using this modification. Further application of the combination of DES and microwave heating is expected to be highly promising and of general utility.

Synthesis of aurones under neutral conditions using a deep eutectic solvent

Aurones are an interesting, but little studied member of the flavanoid family of natural products. Of the various methods available for their synthesis, the simplest involves the condensation of a coumaranone with an aldehyde. This reaction can be perform

Aurones: Small molecule visible range fluorescent probes suitable for biomacromolecules

Aurones, derivatives of 2-benylidenebenzofuran-3 (2H)-one, are natural products that serve as plant pigments. There have been reports that some of these substances fluoresce, but little information about their optical properties is in the literature. In this report, series of aurone derivatives were synthesized as possible fluorescent probes that can be excited by visible light. We found that an amine substituent shifted the lowest energy absorption band from the near-UV to the visible region of the electromagnetic spectrum. Four amine-substituted aurone derivatives were synthesized to explore the effect of this substituent on the absorption and emission properties of the aurone chromophore. The emission maxima and intensities of the molecules are strongly dependent on the nature of the substituent and the solvent polarity. Overall, the emission intensity increases and the maximum wavelength decreases in less polar solvents; thus, the aurones may be useful probes for hydrophobic sites on biological molecules. A limited investigation with model protein, nucleic acid and fixed cells supports this idea. It is known that the sulfur analog of aurone can undergo photoinduced E/Z isomerization. This possibility was investigated for one of the aminoaurones, which was observed to reversible photoisomerize. The two isomers have similar absorption spectra, but the emission properties are distinct. We conclude that appropriately substituted aurones are potentially useful as biological probes and photoswitches. Springer Science+Business Media, LLC 2011.

ALUMINA-MEDIATED CONDENSATION. A SIMPLE SYNTHESIS OF AURONES

A simple and high yielding synthesis of aurones (2-phenylmethylene-3(2H)-benzofuranones) is described which occurs under mild conditions on alumina surface using readily available benzofuranones and arylaldehydes.Key Words: Aurones; 2-Phenylmethylene-3(2H)-benzofuranones; Solid Surface; Alumina

REACTION DE DIVERSES 2-ARYLIDENE-BENZOFURAN-3-ONES AVEC LA DIPHENYLNITRILIMINE. UNE NOUVELLE SYNTHESE D'ORTHO-HYDROXYBENZOYLPYRAZOLES

A new synthesis of ortho-hydroxybenzoylpyrazoles in one step from 2-arylidene-benzofuran-3-ones, via cycloaddition route and a adduct rearrangement, is recorded.

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.

Cyclodehydrogenation of 2'-hydroxychalcones and dehydrogenation of flavanones using nickel peroxide

Nickel peroxide oxidation of 2'-hydroxychalcones (1) gives flavones (3) in moderate yields, aurones (4) are also formed in cases where the 2/4 position of the starting 1 bears either a strong ?-donor or a ?-acceptor substituent.Flavanones (2) are dehydrogenated with this reagent to the corresponding flavones (3) in very good yields.