19278-82-1

Usage

Uses

Used in Pharmaceutical Industry:
3(2H)-Benzofuranone, 5-hydroxyis used as a bioactive compound for its potential therapeutic applications in various medical conditions. It is known to have antioxidant, anti-inflammatory, and antidiabetic activities, making it a promising candidate for the development of novel drugs and pharmaceutical products.
Used in Drug Development:
3(2H)-Benzofuranone, 5-hydroxyis used in the development of novel drugs and pharmaceutical products due to its potential pharmacological properties. Its antioxidant, anti-inflammatory, and antidiabetic activities have been studied for their potential therapeutic applications in various medical conditions, making it a valuable compound for further research and development in the pharmaceutical industry.

Upstream product

• 60912-82-5 α-chloro-2,5-dihydroxyacetophenone 
• 75717-53-2 2-chloro-1-(2-hydroxy-5-methoxyphenyl)ethan-1-one 
• 150-76-5 4-methoxy-phenol 
• 25015-91-2 2-bromo-1-(2,5-dihydroxyphenyl)ethanone 
• 490-78-8 2,5-Dihydroxyacetophenone 
• 1125-55-9 2-Acetyl-1,4-benzoquinone 
• 144152-29-4 2-acetoxy-5-hydroxyacetophenone 

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 academic research and scientific papers

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.

Benzofuranone derivatives as well as preparation method and application thereof

The invention discloses benzofuranone derivatives as well as a preparation method and medical application thereof, and provides the benzofuranone derivatives, the preparation method thereof and an application of pharmaceutical composition containing the d

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.

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.

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.