5786-54-9

Usage

Uses

Used in Pharmaceutical Industry:
6,4''-DIHYDROXYAURONE is used as a pharmaceutical compound for its potential therapeutic effects. The expression of 6,4''-DIHYDROXYAURONE in this context is that it can be utilized in the development of new drugs due to its unique chemical structure and properties.
Used in Chemical Research:
6,4''-DIHYDROXYAURONE is used as a research compound for studying the properties and behavior of hydroxyaurones. The reason for its use in this application is to gain a deeper understanding of the chemical characteristics of this class of compounds, which can lead to the discovery of new applications and uses.
Used in Material Science:
6,4''-DIHYDROXYAURONE is used as a component in the development of new materials. The unique structure of 6,4''-DIHYDROXYAURONE can potentially contribute to the creation of novel materials with specific properties, making it a valuable compound in material science research.

InChI:InChI=1/C15H10O4/c16-10-3-1-9(2-4-10)7-14-15(18)12-6-5-11(17)8-13(12)19-14/h1-8,16-17H/b14-7-

Upstream product

• 25015-92-3 2-chloro-1-(2,4-dihydroxyphenyl)ethanone 
• 755722-84-0 imine 
• 108-46-3 recorcinol 
• 2688-49-5 6-hydroxy-2-oxo-3H-benzofuran-2-one 
• 123-08-0 4-hydroxy-benzaldehyde 
• 6272-26-0 6-hydroxybenzofuran-3-one 
• 74189-56-3 4-(tetrahydropyran-2-yloxy)benzaldehyde 

Downstream Products

• 82358-52-9 6-hydroxy-2-(4-hydroxybenzyl)benzofuran-3(2H)-one 

Relevant academic research and scientific papers

Design, synthesis and biological activities of dihydroaurones

To widen aurones applicability in achromatic food and cosmetic applications, a series of dihydroaurones were designed to mimic natural aurones as well as synthetic aurones. Dihydroaurones have been synthesized from the corresponding aurones by hydrogenation. These dihydroaurones and their corresponding aurones were screened for antioxidant, anti-inflammatory and tyrosinase enzyme inhibitory activity. Synthesized dihydroaurones (3b-f) displayed superior antioxidant activity in superoxide free radical scavenging assay than the standard gallic acid. Dihydroaurones (3b-f) also exhibited significant tyrosinase enzyme inhibitory activity and two dihydroaurones (3h, 3j) showed promising 5-lipoxygenase inhibitory activity.

Discovery and structure-activity relationship studies of 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives as a novel class of potential therapeutics for inflammatory bowel disease

To develop effective therapeutics for inflammatory bowel disease (IBD), 2-benzylidene-2,3-dihydro-1H-inden-1-one and benzofuran-3(2H)-one derivatives, were designed and synthesized and their structure-activity relationships (SAR) were investigated. Compounds 7, 25, 26, 32, 39, 41, 52, 54, and 55 showed potent inhibitory effect (>70%) on the TNF-α-induced adhesion of monocytes to colon epithelial cells, which is one of the hallmark events leading to IBD. Such inhibitory activity of the compounds correlated with their suppressive activities against the TNF-α-induced production of ROS; ICAM-1 and MCP-1 expression, critical molecules involved in monocyte-epithelial adhesion; and NF-κB transcriptional activity. In addition, compounds 41 and 55 significantly suppressed the lipopolysaccharide (LPS)-induced expression of the TNF-α gene, with compound 55 showing better efficacy. This inhibition of TNF-α expression by compounds 41 and 55 corresponded to their additional inhibitory activity against AP-1 transcriptional activity, which is another transcription factor required for high level TNF-α expression. The strong inhibitory activity of compound 55 against an in vivo colitis model was confirmed by its dose-dependent inhibitory activity in a rat model of 2,4,6-trinitrobenzenesulfonic acid (TNBS)-induced colitis, demonstrating compound 55 as a new potential candidate for the development of therapeutics against IBD.

Composition for preventing or treating inflammatory bowel disease comprising benzylidene benzofuranone compound as an active ingredient

The present invention relates to a composition for preventing and treating inflammatory bowel disease comprising a benzylidene benzofuranone derivative compound as an active ingredient. The benzylidene benzofuranone derivative compound is effective in maintaining the thickness of small intestine and the length of large intestine to normal states, and inhibiting inflammation with respect to large intestine, thereby being used as a pharmaceutical composition for preventing and treating inflammatory bowel disease.

Investigation of binding-site homology between mushroom and bacterial tyrosinases by using aurones as effectors

Tyrosinase is a copper-containing enzyme found in plants and bacteria, as well as in humans, where it is involved in the biosynthesis of melanin-type pigments. Tyrosinase inhibitors have attracted remarkable research interest as whitening agents in cosmetology, antibrowning agents in food chemistry, and as therapeutics. In this context, commercially available tyrosinase from mushroom (TyM) is frequently used for the identification of inhibitors. This and bacterial tyrosinase (TyB) have been the subjects of intense biochemical and structural studies, including X-ray diffraction analysis, and this has led to the identification of structural homology and divergence among enzymes from different sources. To better understand the behavior of potential inhibitors of TyM and TyB, we selected the aurone family - previously identified as potential inhibitors of melanin biosynthesis in human melanocytes. In this study, a series of 24 aurones with different hydroxylation patterns at the A- and B-rings were evaluated on TyM and TyB. The results show that, depending on the hydroxylation pattern of A- and B-rings, aurones can behave as inhibitors, substrates, and activators of both enzymes. Computational analysis was performed to identify residues surrounding the aurones in the active sites of both enzymes and to rationalize the interactions. Our results highlight similarities and divergence in the behavior of TyM and TyB toward the same set of molecules. A lighter future: Aurones have been identified as inhibitors of melanin biosynthesis. In this study, 24 aurones were evaluated on mushroom and bacterial tyrosinases (TyM and TyB). The compounds behaved as inhibitors, substrates, or activators of both enzymes. Our results highlight similarities and differences in behavior between TyM and TyB with the same set of molecules.

Synthesis of aurones and their inhibitory effects on nitric oxide and PGE2 productions in LPS-induced RAW 264.7 cells

Sulfuretin is one of major constituents of Rhus verniciflua that exerts anti-inflammatory activities. Some of aurones were synthesized as sulfuretin derivatives and evaluated for their abilities to inhibit NO and PGE2 production in LPS-induced RAW 264.7 cells in order to reveal the relationship. Of the aurones synthesized in the present study, 2h and 2i, which possess C-6 hydroxyl group in A-ring and methoxy substituents in B-ring, more potently inhibited NO and PGE2 production and were less cytotoxic than sulfuretin.

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.

Functionalized aurones as inducers of NAD(P)H:quinone oxidoreductase 1 that activate AhR/XRE and Nrf2/ARE signaling pathways: Synthesis, evaluation and SAR

The chemopreventive potential of functionalized aurones and related compounds as inducers of NAD(P)H:quinone oxidoreductase 1 (NQO1, EC 1.6.99.2) are described. Several 4,6-dimethoxy and 5-hydroxyaurones induced NQO1 activity of Hepa1c1c7 cells by 2-fold at submicromolar concentrations, making these the most potent inducers to be identified from this class. Mechanistically, induction of NQO1 was mediated by the activation of AhR/XRE and Nrf2/ARE pathways, indicating that aurones may be mixed activators of NQO1 induction or agents capable of exploiting the proposed cross-talk between the AhR and Nrf2 gene batteries. QSAR analysis by partial least squares projection to latent structures (PLS) identified size parameters, in particular those associated with non-polar surface areas, as an important determinant of induction activity. These were largely determined by the substitution on rings A and B. A stereoelectronic role for the exocyclic double bond as reflected in the E LUMO term was also identified. The electrophilicity of the double bond or its effect on the conformation of the target compound are possible key features for induction activity.

Discovery of benzylidenebenzofuran-3(2H)-one (aurones) as inhibitors of tyrosinase derived from human melanocytes

Tyrosinase is a copper-dependent enzyme which converts L- tyrosine to dopaquinone and is involved in different biological processes such as melanogenesis and skin hyperpigmentation. The purpose of this study was to investigate naturally occurring aurones (Z-benzylidenebenzofuran-3(2H)-one) and analogues as human tyrosinase inhibitors. Several aurones bearing hydroxyl groups on A-ring and different substituents on B-ring were synthesized and evaluated as inhibitors of human melanocyte-tyrosinase by an assay which measures tyrosinase-catalyzed L-Dopa oxidation. We found that unsubstituted aurones were weak inhibitors; however, derivatives with two or three hydroxyl groups preferably at 4,6 and 4′ positions are able to induce significant tyrosinase inhibition. The most potent aurone was found to be the naturally occurring 4,6,4′-trihydroxyaurone which induces 75% inhibition at 0.1 mM concentration and is highly effective when compared to kojic acid, one of the best tyrosinase inhibitors known so far (the latter is completely inactive at such concentrations). Active aurones are devoid of toxic effects as shown by in vivo studies.

Neoraufuracin and Ambofuracin. Two Novel 2-Benzyl-2-O-(methyl-β-D-glucopyranos-2-yl)-trans-2,3-dihydrobenzofurans. Synthesis of the Methylated Aglycone

The structures of two novel 2-benzyl-3-O-(methyl-β-D-glucopyranos-2-yl)-trans-2,3-dihydrobenzofurans are elucidated using high resolution 1H n.m.r., 13C n.m.r., and field-desorption mass spectrometry, and also by synthesis of a derivative of the aglycone moiety common to both compounds.