3542-63-0

Basic information

• Product Name: 4H-1-Benzopyran-4-one, 5,8-dihydroxy-2-phenyl-7-(phenylmethoxy)-
• Synonyms: 7-Benzyloxy-5,8-dihydroxy-2-phenyl-chromen-4-on;7-Benzyloxy-5,8-dihydroxy-flavon
• CAS NO: 3542-63-0
• Molecular Formula: C22H16O5
• Molecular Weight: 360.366
• Mol File: 3542-63-0.mol
• Article Data: 4

Chemical Properties

• CAS DataBase Reference: 4H-1-Benzopyran-4-one, 5,8-dihydroxy-2-phenyl-7-(phenylmethoxy)-(CAS DataBase Reference)
• NIST Chemistry Reference: 4H-1-Benzopyran-4-one, 5,8-dihydroxy-2-phenyl-7-(phenylmethoxy)-(3542-63-0)
• EPA Substance Registry System: 4H-1-Benzopyran-4-one, 5,8-dihydroxy-2-phenyl-7-(phenylmethoxy)-(3542-63-0)

Safety Data

• Hazardous Substances Data: 3542-63-0(Hazardous Substances Data)

Upstream product

• 146329-57-9 tetramethylammonium 5,7-dihydroxy-4-oxo-2-phenyl-4H-chromen-8-yl sulfate 
• 100-44-7 benzyl chloride 
• 480-40-0 5,7-dihydroxy-2-phenyl-chromen-4-one 
• 110506-85-9 7-(benzyloxy)-5-hydroxy-2-phenyl-4H-chromen-4-one 

Downstream Products

• 3542-64-1 7-benzyloxy-5-hydroxy-8-methoxy-2-phenyl-4H-chromen-4-one 
• 742076-91-1 7-benzyloxy-5,8-dimethoxy-2-phenyl-chromen-4-one 

Relevant articles and documents

Discovery of Wogonin-based PROTACs against CDK9 and capable of achieving antitumor activity

Wogonin is a natural product isolated from the Scutellaria baicalensis and has been proved to be a potent and selective inhibitor of CDK9. Using this scaffold, we designed and synthesized a series of proteolysis targeting chimeras (PROTACs) targeting CDK9 by recruiting ubiquitin E3 ligase cereblon (CRBN). For constructing diverse Wogonin-based PROTACs, a “click chemistry” approach was employed for the synthesis of CDK9-targeting PROTACs. The results of western blotting assays showed that compounds containing triazole group in the linker could selectively downregulate the intracellular CDK9 level. Among these compounds, 11c could selectively degrade CDK9 in a concentration-dependent manner. In addition, the application of the proteasome inhibitor MG132 and CRBN siRNA silencing confirmed that 11c could promote the proteasome-dependent and CRBN-dependent degradation. Consistent with the degradation of the CDK9 protein, 11c selectively inhibits proliferation of CDK9-overexpressed cancer cells. Thus, our Wogonin-based PROTAC would be an efficient probe that induces the degradation of CDK9.

Synthesis, evaluation and quantitative structure–activity relationship (QSAR) analysis of Wogonin derivatives as cytotoxic agents

A novel series of 49 wogonin derivatives were synthesized by introducing group at 7-, 8- or B ring of wogonin. The cytotoxic activities against HepG2, A549 and BCG-823 cancer cell lines were also investigated in vitro. Several of them showed obvious cytotoxic activities and compound 3h possessed the highest potency against HepG2, A549, and BCG-823 with IC50 values of 1.07 μM, 1.74 μM and 0.98 μM, respectively. A quantitative structure-activity relationship (QSAR) study of these synthetic derivatives as well as wogonin indicated that high solubility and low octanol/water partition coefficient are favorable, and excessive electrostatic properties and refractivity are unfavorable for the cytotoxic activities of these wogonin derivatives. These findings and results provide a base for further investigations.