19278-82-1

Basic information

• Product Name: 3(2H)-Benzofuranone, 5-hydroxy-
• Synonyms: 3(2H)-Benzofuranone, 5-hydroxy-;5-HYDROXY-3(2H)-BENZOFURANONE
• CAS NO: 19278-82-1
• Molecular Formula: C₈H₆O₃
• Molecular Weight: 150.13
• Mol File: 19278-82-1.mol
• Article Data: 7

Chemical Properties

• Appearance: /
• CAS DataBase Reference: 3(2H)-Benzofuranone, 5-hydroxy-(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Benzofuranone, 5-hydroxy-(19278-82-1)
• EPA Substance Registry System: 3(2H)-Benzofuranone, 5-hydroxy-(19278-82-1)

Safety Data

• Hazardous Substances Data: 19278-82-1(Hazardous Substances Data)

Usage

General Description

5-hydroxy-3(2H)-benzofuranone is a chemical compound with a molecular formula C8H6O3 and a molecular weight of 150.13 g/mol. It is a benzofuranone derivative that contains a hydroxyl group at the fifth carbon position. 3(2H)-Benzofuranone, 5-hydroxy- can be found in various natural sources such as plants and fruits, and it has been identified as a bioactive compound with potential pharmacological properties. It is known to have antioxidant, anti-inflammatory, and antidiabetic activities, and it has been studied for its potential therapeutic applications in various medical conditions. Additionally, 5-hydroxy-3(2H)-benzofuranone has been investigated for its use in the development of novel drugs and pharmaceutical products.

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Downstream Products

• 1234351-48-4 (Z)-2-(3-hydroxybenzylidene)-5-hydroxybenzofuran-3(2H)-one 
• 1234351-64-4 (Z)-5-hydroxy-2-(4-methylbenzylidene)benzofuran-3(2H)-one 
• 1234351-44-0 (Z)-5-hydroxy-2-(4-chlorobenzylidene)benzofuran-3(2H)-one 
• 1234351-40-6 2-(2'-chlorobenzylidene)-5-hydroxybenzofuran-3(2H)-one 
• 1234351-50-8 (Z)-5-hydroxy-2-(4-hydroxybenzylidene)benzofuran-3(2H)-one 
• 1234351-38-2 (Z)-5-hydroxy-2-benzylidene-benzofuran-3(2H)-one 
• 1234351-58-6 (Z)-5-hydroxy-2-(4-methoxybenzylidene)benzofuran-3(2H)-one 
• 1234351-46-2 (Z)-2-(2-hydroxybenzylidene)-5-hydroxybenzofuran-3(2H)-one 
• 1234351-42-8 (Z)-2-(3-chlorobenzylidene)-5-hydroxybenzo[b]furan-3-one 
• 1234351-55-3 (Z)-2-(3-methoxybenzylidene)-5-hydroxybenzo[b]furan-3-one 
• 1234351-52-0 5-hydroxy-2-(2'-methoxybenzylidene)benzofuran-3(2H)-one 
• 1261274-06-9 (Z)-5-hydroxy-2-(4-trifluoromethylbenzylidene)benzofuran-3(2H)-one 
• 1261274-11-6 (Z)-5-hydroxy-2-(4-(1-piperidinyl)benzylidene)benzofuran-3(2H)-one 
• 1261274-12-7 (Z)-5-hydroxy-2-(4-(1-pyrrolidinyl)benzylidene)benzofuran-3(2H)-one 

Relevant articles and documents

Design and synthesis of novel senkyunolide analogues as neuroprotective agents

A class of senkyunolide analogues bearing benzofuranone fragment were designed, synthesized and evaluated for their neuroprotective effect in models of oxygen glucose deprivation (OGD) and oxidative stress. All tested compounds showed neuroprotection profile based on the cell viability assay. In particular, derivatives 1f–1i possessing furoxan-based nitric oxide releasing functionality exhibited significant biological activities in OGD models. More importantly, compound 1g containing short linker with furoxan displayed the most potent neuroprotection at the concentration of 100 μM (cell survival up to 145.2%). Besides, 1g also showed the middle level neuroprotective effect in model of oxidative stress.

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.

Design, synthesis and discovery of 5-hydroxyaurone derivatives as growth inhibitors against HUVEC and some cancer cell lines

A series of 4′-substituted 5-hydroxyaurone derivatives were synthesized and their inhibitory activities against the proliferation of endothelial cells and two cancer cell lines were studied. Some of these compounds functioned as potent inhibitors against the proliferation of endothelial cells and cancer cells but possessed much weaker cytotoxic activities against non-cancer cell line of CCC-HPF-1. It was demonstrated that two most active compounds 16 and 27 effectively inhibited in vitro endothelial cell motility and tube formation, which are basic properties of endothelial cells for angiogenesis. Moreover, 16 and 27 also showed significant activities against in vitro cancer cell invasion, indicating that they have potential to inhibit cancer metastasis. These composite results suggest that 4′-substituted 5-hydroxyaurone is indeed a candidate structural scaffold for anticancer agent targeting activated endothelial cells and fast-proliferating cancer cells.