112980-31-1

Basic information

• Product Name: 3(2H)-Benzofuranone, 2-[(4-hydroxyphenyl)methylene]-, (2Z)-
• CAS NO: 112980-31-1
• Molecular Formula: C15H10O3
• Molecular Weight: 238.243
• Mol File: 112980-31-1.mol
• Article Data: 16

Chemical Properties

• CAS DataBase Reference: 3(2H)-Benzofuranone, 2-[(4-hydroxyphenyl)methylene]-, (2Z)-(CAS DataBase Reference)
• NIST Chemistry Reference: 3(2H)-Benzofuranone, 2-[(4-hydroxyphenyl)methylene]-, (2Z)-(112980-31-1)
• EPA Substance Registry System: 3(2H)-Benzofuranone, 2-[(4-hydroxyphenyl)methylene]-, (2Z)-(112980-31-1)

Safety Data

• Hazardous Substances Data: 112980-31-1(Hazardous Substances Data)

Upstream product

• 7169-34-8 3-oxo-2,3-dihydrobenzo[b]furan 
• 123-08-0 4-hydroxy-benzaldehyde 
• 13323-66-5 2',4-dihydroxychalcone 
• 122-59-8 2-phenoxyacetic acid 
• 53074-73-0 2-(2-chloroacetyl)phenol 
• 620-73-5 phenyl chloroacetate 
• 108-95-2 phenol 
• 3327-24-0 1-(2-hydroxyphenyl)-3-(4-methoxyphenyl)-2-propen-1-one 
• 123-11-5 4-methoxy-benzaldehyde 
• 36685-41-3 (Z)-4'-methoxyaurone 
• 118-93-4 o-hydroxyacetophenone 

Downstream Products

• 70170-79-5 (Z)-2-(4-((3-oxobenzofuran-2(3H)-ylidene)methyl)phenoxy)acetic acid 

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.

The first synthesis of peracetyl glycosyl aurone derivatives and aurone glucosides

Aurones, a sub-class of the flavonoids with proven therapeutic importance, also exist in variously glycosylated forms. Although a large number of glycosylated aurone derivatives have been isolated from plant sources, no syntheses have been reported yet. Inspired from this gap, here we report the first synthesis of peracetylated glycosyl derivatives of synthetic aurones. The direct O-glycosylation was achieved by reacting 6-hydroxy aurones with 2, 3, 4, 6-tetra-O-acetyl-α-D glucopyranosyl bromide in the presence of a phase transfer catalyst tetrabutylammonium bromide (TBAB). The successful synthesis of aurone glycosides (33 examples) in 60–92% yield will benefit the synthesis of combinatorial libraries of glycosylated aurones for their biological study and comparison with non-glycosylated aurones.

Aurones as new porcine pancreatic α-amylase inhibitors

Background: Aurones, (Z)-2-benzylidenebenzofuran-3-one derivatives, are naturally-occurring structural isomers of flavones, with promising pharmacological potential. Methods: In this study, the structural requirements for the inhibition of porcine pancreatic α-amylase by hydroxylated or methoxylated aurone derivatives were investigated by assessing their in vitro biological activities against porcine pancreatic α-amylase. Results: The structure-activity relationship of these inhibitors based on both in vitro and in silico findings showed that the hydrogen bonds between the OH groups of the A or B ring of (Z)-benzylidenebenzofuran-3-one derivatives and the catalytic residues of the binding site are crucial for their inhibitory activities. Conclusion: It seems that the OH groups in aurones inhibit α-amylase in a manner similar to that of OH groups in flavones and flavonols.