24418-86-8

Basic information

• Product Name: 2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V
• Synonyms: 2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V;SKI V;2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one;Sphingosine Kinase Inhibitor V;(2E)-2-[(3,4-dihydroxyphenyl)methylidene]-1-benzofuran-3-one
• CAS NO: 24418-86-8
• Molecular Formula: C₁₅H₁₀O₄
• Molecular Weight: 254.24
• Mol File: 24418-86-8.mol
• Article Data: 7

Chemical Properties

• Boiling Point: 493.2±45.0 °C(Predicted)
• Appearance: /
• Density: 1.489±0.06 g/cm3(Predicted)
• Storage Temp.: 2-8°C
• PKA: 8.99±0.10(Predicted)
• CAS DataBase Reference: 2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V(24418-86-8)
• EPA Substance Registry System: 2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, Sphingosine Kinase Inhibitor V(24418-86-8)

Safety Data

• Hazardous Substances Data: 24418-86-8(Hazardous Substances Data)

Usage

General Description

2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one, also known as Sphingosine Kinase Inhibitor V, is a chemical compound that acts as an inhibitor of sphingosine kinase, an enzyme involved in the regulation of cell survival, proliferation, and migration. By inhibiting this enzyme, 2-(3,4-Dihydroxy-benzylidene)-benzofuran-3-one has the potential to disrupt the signaling pathways involved in various cellular processes, making it a promising candidate for anti-cancer and anti-inflammatory therapies. Its structure contains a benzofuran ring system with hydroxyl and aldehyde functional groups, giving it specific binding properties to its target enzyme. Further research on this compound may lead to the development of novel pharmaceutical drugs for the treatment of various diseases.

Upstream product

• 53074-73-0 2-(2-chloroacetyl)phenol 
• 620-73-5 phenyl chloroacetate 
• 108-95-2 phenol 
• 63831-46-9 (Z)-2-(3,4-dimethoxybenzylidene)benzofuran-3(2H)-one 
• 79140-20-8 2'-hydroxy-3,4-dimethoxychalcone 
• 120-14-9 3,4-dimethoxy-benzaldehyde 
• 139-85-5 3,4-dihydroxybenzaldehyde 
• 118-93-4 o-hydroxyacetophenone 
• 88191-21-3 3,4,2'-trihydroxy-trans-chalcone 
• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 

Relevant articles and documents

Flavone inspired discovery of benzylidenebenzofuran-3(2H)-ones (aurones) as potent inhibitors of human protein kinase CK2

In this work, we describe the design, synthesis and SAR studies of 2-benzylidenebenzofuran-3-ones (aurones), a new family of potent inhibitors of CK2. A series of aurones have been synthesized. These compounds are structurally related to the synthetic flavones and showed nanomolar activities towards CK2. Biochemical tests revealed that 20 newly synthesized compounds inhibited CK2 with IC50 values in the nanomolar range. Further property-based optimization of aurones was performed, yielding a series of CK2 inhibitors with enhanced lipophilic efficiency. The most potent compound 12m (BFO13) has CLipE = 4.94 (CLogP = 3.5; IC50 = 3.6 nM) commensurable with the best known inhibitors of CK2.

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.

Synthesis, structural revision, and biological activities of 4′-chloroaurone, a metabolite of marine brown alga Spatoglossum variabile

4′-Chloroaurone (1a), the only aurone reported from a marine source, Spatoglossum variabile was synthesized from 2-hydroxyacetophenone along with six structural analogs. The products obtained were Z-isomers and these were converted into E-isomers by photo