39777-72-5

Basic information

• Product Name: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one
• Synonyms: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one
• CAS NO: 39777-72-5
• Molecular Weight: 414.415
• Mol File: 39777-72-5.mol

Chemical Properties

• CAS DataBase Reference: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one(CAS DataBase Reference)
• NIST Chemistry Reference: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one(39777-72-5)
• EPA Substance Registry System: 2-(3,4-dihydroxyphenyl)-3,5,7-trihydroxy-8-((4-methylpiperazin-1-yl)methyl)-4H-chromen-4-one(39777-72-5)

Safety Data

• Hazardous Substances Data: 39777-72-5(Hazardous Substances Data)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 50-00-0 formaldehyd 
• 18003-33-3 3',4',5,6,7-pentahydroxyflavone 
• 117-39-5 quercetol 

Relevant articles and documents

Mannich aminomethylation of flavonoids and anti-proliferative activity against breast cancer cell

We herein report Mannich aminomethylation of variously structural flavonoids and their biological evaluation against human breast cancer cell. Mannich reaction showed that substitution at C-6 position depends on amine basicity and C-ring feature of flavon

The synthesis, antimalarial activity and CoMFA analysis of novel aminoalkylated quercetin analogs

A series of novel aminoalkylated quercetin analogs, prepared via the Mannich reaction of various primary and secondary amines with formaldehyde, were tested for antimalarial activity. The compounds were screened against three drug resistant malarial strains (D6, C235 and W2) and were found to exhibit sub-micromolar activity across all three strains (0.065-13.0 μM). The structure-activity relationship determined from the antimalarial activity data suggests the inclusion of phenethyl amine sidechains on the quercetin scaffolding is necessary for potent activity. Additionally, the most active compounds ((5) and (6)) were tested for both early and late stage anti-gametocytocidal activity. Finally, the antimalarial activity data were utilized to construct comparative molecular field analysis (CoMFA) models to be used for further compound refinement.

Nitrogen-containing flavonoid analogues as CDK1/cyclin B inhibitors: Synthesis, SAR analysis, and biological activity

A series of nitrogen-containing flavonoid analogues were designed and synthesized by Mannich reaction, and screened for the inhibitory activities of cyclin-dependent kinases using a FRET-based biochemical assay method. The results showed that C-8 nitrogen-containing baicalein analogues 3a-3f exhibited potent CDK1/Cyclin B inhibitory activities. 5,6,7-Trihydroxy-8-(dimethylaminomethyl)-2-phenyl-4H-chromen-4-one 3a, 5,6,7-trihydroxy-8-(pyrrolid inylmethyl)-2-phenyl-4H-chromen-4-one 3b, and 5,6,7-trihydroxy-8-(piperidinylmethyl)-2-phenyl-4H-chromen-4-one 3c (IC50 1.05-1.28 μM) were about sixfold more potent than baicalein 2 (IC50 6.53 μM). 5,6,7-Trihydroxy-8-(morpholinomethyl)-2-phenyl-4H-chromen-4-one 3d, 5,6,7-trihydroxy-8-(thiomorpholinomethy)-2-phenyl-4H-chrom en-4-one 3e, and 5,6,7-trihydroxy-8-(4-methylpiperazinylmethyl)-2-phenyl-4H-chromen-4-one 3f (IC50 0.27-0.38 μM) were about 20-fold more potent than baicalein, and were at the same level as flavopiridol (IC50 0.33 μM).