19278-81-0

Basic information

• Product Name: 3(2H)-Benzofuranone, 4-hydroxy-
• Synonyms: 3(2H)-Benzofuranone, 4-hydroxy-;4-Hydroxy-3(2H)-benzofuranone;4-Hydroxybenzofuran-3(2H)-one;4-Hydroxycoumaran-3-one;4-Hydroxy-benzofuran-3-one
• CAS NO: 19278-81-0
• Molecular Formula: C₈H₆O₃
• Molecular Weight: 150.13
• Mol File: 19278-81-0.mol

Chemical Properties

• Melting Point: 117℃
• Boiling Point: 331.8±42.0 °C(Predicted)
• Appearance: /
• Density: 1.436±0.06 g/cm3(Predicted)
• PKA: 9.79±0.20(Predicted)
• CAS DataBase Reference: 3(2H)-Benzofuranone, 4-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Benzofuranone, 4-hydroxy-(19278-81-0)
• EPA Substance Registry System: 3(2H)-Benzofuranone, 4-hydroxy-(19278-81-0)

Safety Data

• Hazardous Substances Data: 19278-81-0(Hazardous Substances Data)

Upstream product

• 699-83-2 2,6-dihydroxylacetophenone 
• 2491-40-9 2-bromo-1-(2,6-dihydroxy-phenyl)-ethanone 
• 26674-05-5 acetic acid 2-acetyl-3-hydroxyphenyl ester 
• 75-77-4 chloro-trimethyl-silane 
• 1146968-51-5 C₁₄H₂₄O₃Si₂ 
• 144152-28-3 2,6-diacetoxyacetophenone 
• 444711-04-0 2-bromo-1-(2,6-diacetoxy-phenyl)-ethanone 

Downstream Products

• 480-97-7 4-hydroxybenzofuran 
• 1198275-68-1 4-{3-[(Z)-(4-hydroxy-3-oxo-1-benzofuran-2(3H)-ylidene)methyl]-1-methyl-1H-pyrrolo[2,3-b]pyridin-4-yl}-N,N-dimethylbenzamide 
• 1198275-85-2 (2Z)-4-hydroxy-2-({1-methyl-4-[4-(morpholin-4-ylcarbonyl)phenyl]-1H-pyrrolo[2,3-b]pyridin-3-yl}methylene)-1-benzofuran-3(2H)-one 
• 1198276-03-7 (2Z)-4-hydroxy-2-{[4-(4-{[4-(2-hydroxyethyl)piperazin-1-yl]carbonyl}phenyl)-1-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl]methylidene}-1-benzofuran-3(2H)-one 
• 173394-21-3 (Z)-2-(2,4-dihydroxybenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 1314713-68-2 C₂₀H₂₀N₂O₃*ClH 
• 1314713-67-1 (Z)-2-(4-tert-butylbenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 1314713-62-6 (Z)-2-(2,4,6-trimethoxybenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 1314713-66-0 (Z)-2-(4-butylbenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 67140-91-4 (Z)-2-benzylidene-4-hydroxybenzofuran-3(2H)-one 
• 1314713-44-4 (Z)-2-(3-hydroxybenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 1314713-56-8 (Z)-2-(2,4-dimethylbenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 1314713-72-8 (Z)-2-(2-fluorobenzylidene)-4-hydroxybenzofuran-3(2H)-one 
• 1314839-58-1 (Z)-2-(4-(4-methylpiperazin-1-yl)benzylidene)-4-hydroxybenzofuran-3(2H)-one 

Relevant articles and documents

Para-substituted dihydrofurocoumarin neuraminidase inhibitor and preparation method and application thereof

The invention relates to the technical field of biological medicines, and particularly relates to a para-substituted dihydrofurocoumarin neuraminidase inhibitor and a preparation method and application thereof. The para-substituted dihydrofurocoumarin neuraminidase inhibitor has a structure as shown in a formula I. The para-substituted dihydrofurocoumarin neuraminidase inhibitor has a novel compound structure, and experiments show that the para-substituted dihydrofurocoumarin neuraminidase inhibitor has good neuraminidase inhibition activity and is expected to be used for preparing medicines for inhibiting neuraminidase activity

Aurone derivatives as promising antibacterial agents against resistant Gram-positive pathogens

A set of variously substituted aurones was synthesized and evaluated against Methicillin-Resistant S. aureus (MRSA) and P. aeruginosa. Several analogues were found active against MRSA, but no effect was recorded against P. aeruginosa. Compounds 27, 30 and 33 showed low cytotoxicity, and were tested against a full range of bacterial (Gram-positive and Gram-negative) and fungal species, including resistant strains. These aurones displayed a selective inhibition of Gram-positive bacteria with excellent Therapeutic Index values, while showing no significant action on several Gram-negative strains, H. pylori and V. alginolyticus being the only susceptible strains among the Gram-negative bacteria tested. A permeabilization assay showed that the antibacterial activity of at least some of the aurones could be linked to alterations of the bacterial membrane. Overall, this study endorses the use of the aurone scaffold for the development of new potent and selective antibacterial agents.

Discovery of benzofuran-3(2H)-one derivatives as novel DRAK2 inhibitors that protect islet β-cells from apoptosis

Death-associated protein kinase-related apoptosis-inducing kinase-2 (DRAK2) is a serine/threonine kinase that plays a key role in a wide variety of cell death signaling pathways. Inhibition of DRAK2 was found to efficiently protect islet β-cells from apoptosis and hence DRAK2 inhibitors represent a promising therapeutic strategy for the treatment of diabetes. Only very few chemical entities targeting DRAK2 are currently known. We carried out a high throughput screening and identified compound 4 as a moderate DRAK2 inhibitor with an IC50value of 3.15?μM. Subsequent SAR studies of hit compound 4 led to the development of novel benzofuran-3(2H)-one series of DRAK2 inhibitors with improved potency and favorable selectivity profiles against 26 selected kinases. Importantly, most potent compounds 40 (IC50?=?0.33?μM) and 41 (IC50?=?0.25?μM) were found to protect islet β-cells from apoptosis in dose-dependent manners. These data support the notion that small molecule inhibitors of DRAK2 represents a promising strategy for the treatment of diabetes.

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.

Structure - activity relationship studies leading to the identification of (2E)-3-[l-[(2,4-dichlorophenyl)methyl]-5-fluoro-3-methyl-lH-indol-7-yl]-N-[(4, 5-dichloro-2-thienyl)sulfonyl]-2-propenamide (DG-041), a potent and selective prostanoid EP3 receptor antagonist, as a novel antiplatelet agent that does not prolong bleeding

The EP3 receptor on the platelet mediates prostaglandin E 2 potentiation of thrombogenic coagonists including collagen and adenosine diphosphate (ADP). A pharmacophore driven approach led to the identification of diverse peri-substituted heterocycles as potent and selective EP3 receptor antagonists. A simultaneous chemical optimization and druglike assessment of prioritized molecules converged on a lead compound 50 (DG-041) that displayed favorable in vitro and functional activities as an inhibitor of human platelet aggregation. This agent is currently in human clinical trials for the treatment of atherothrombosis.

3-SUBSTITUTED-1H-INDOLE, 3-SUBSTITUTED-1H-PYRROLO[2,3-B]PYRIDINE AND 3-SUBSTITUTED-1H-PYRROLO[3,2-B]PYRIDINE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES

The invention relates to 3-substituted-1H-indole, 3-substituted-1H-pyrrolo[2,3-b]pyridine, and 3-substituted-1H-pyrrolo[3,2-b]pyridine compounds of the Formula (I): or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

3-SUBSTITUTED-1H-PYRROLO[2,3-B]PYRIDINE AND 3-SUBSTITUTED-1H-PYRROLO[3,2-B]PYRIDINE COMPOUNDS, THEIR USE AS MTOR KINASE AND PI3 KINASE INHIBITORS, AND THEIR SYNTHESES

The invention relates to 3-substituted-1H-pyrrolo[2,3-b]pyridine, and 3-substituted-1H-pyrrolo[3,2-b]pyridine compounds of the Formula 1: or a pharmaceutically acceptable salt thereof, wherein the constituent variables are as defined herein, compositions comprising the compounds, and methods for making and using the compounds.

An Adler-Becker oxidation approach to vinigrol

Detailed in this Letter is an Adler-Becker oxidation strategy towards vinigrol. The effects of substitution were shown to greatly impact successes of both the oxidative dearomatization and Diels-Alder reactions.

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.

A method of cosmetic depigmentation care by applying at least one aurone

At least one aurone or a natural or synthetic derivative of aurone, or an analogue of aurone, in which the independent phenyl ring can be substituted by a heterocycle of pyrrole, imidazole, triazole, pyridine, furan, or thiophene type, is disclosed as a cosmetic agent, or as an active substance, for the manufacture either of a cosmetic composition, or of a pharmaceutical composition, notably a dermatological composition, having a melanogenesis-inhibiting activity or a depigmenting activity, or an anti-tyrosinase activity.