4657-07-2

Basic information

• Product Name: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
• Synonyms: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one
• CAS NO: 4657-07-2
• Molecular Weight: 504.491
• Mol File: 4657-07-2.mol
• Article Data: 2

Chemical Properties

• CAS DataBase Reference: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one(4657-07-2)
• EPA Substance Registry System: 2-(3,4-dimethoxyphenyl)-5,7-dimethoxy-6-((2S,3R,4R,5S,6R)-3,4,5-trihydroxy-6-(hydroxymethyl)tetrahydro-2H-pyran-2-yl)-4H-chromen-4-one(4657-07-2)

Safety Data

• Hazardous Substances Data: 4657-07-2(Hazardous Substances Data)

Upstream product

• 4261-42-1 isoorientin 
• 18107-18-1 diazomethyl-trimethyl-silane 
• 4261-42-1 isoorientin 

Relevant articles and documents

Discovery of Selective, Substrate-Competitive, and Passive Membrane Permeable Glycogen Synthase Kinase-3β Inhibitors: Synthesis, Biological Evaluation, and Molecular Modeling of New C-Glycosylflavones

Glycogen synthase kinase-3β (GSK-3β) is a key enzyme responsible for tau hyperphosphorylation and is a viable therapeutic target of Alzheimer's disease (AD). We developed a new class of GSK-3β inhibitors based on the 6-C-glycosylflavone isoorientin (1). The new inhibitors are passive membrane permeable and constitutively attenuate GSK-3β mediated tau hyperphosphorylation and amyloid neurotoxicity in an AD cellular model. Enzymatic assays and kinetic studies demonstrated that compound 30 is a GSK-3β substrate-competitive inhibitor with distinct kinase selectivity, isoform-selectivity and over 310-fold increased potency as compared to 1. Structure-activity relationship analyses and in silico modeling suggest the mechanism of actions by which the hydrophobic, π-cation, and orthogonal multipolar interactions of 30 with the substrate site are critical for the GSK-3β inhibition and selectivity. The results provide new insights into GSK-3β drug discovery. The new inhibitors are valuable chemical probes and drug leads with therapeutic potential to tackle AD and other GSK-3β relevant diseases.