96225-96-6

Basic information

• Product Name: 4-AMINO-6-(4-METHYL-1-PIPERAZINYL)PYRIMIDINE
• Synonyms: 4-AMINO-6-(4-METHYL-1-PIPERAZINYL)PYRIMIDINE;6-(4-Methylpiperazin-1-yl)pyriMidin-4-aMine;6-(4-methyl-1-piperazinyl)-4-Pyrimidinamine
• CAS NO: 96225-96-6
• Molecular Formula: C9H15N5
• Molecular Weight: 193.25
• Product Categories: Heterocycle-Pyrimidine series
• Mol File: 96225-96-6.mol
• Article Data: 3

Chemical Properties

• Boiling Point: 392.133 °C at 760 mmHg
• Flash Point: 190.955 °C
• Appearance: /
• Density: 1.197 g/cm³
• Vapor Pressure: 0mmHg at 25°C
• Refractive Index: 1.599
• Storage Temp.: Keep in dark place,Inert atmosphere,Room temperature
• CAS DataBase Reference: 4-AMINO-6-(4-METHYL-1-PIPERAZINYL)PYRIMIDINE(CAS DataBase Reference)
• NIST Chemistry Reference: 4-AMINO-6-(4-METHYL-1-PIPERAZINYL)PYRIMIDINE(96225-96-6)
• EPA Substance Registry System: 4-AMINO-6-(4-METHYL-1-PIPERAZINYL)PYRIMIDINE(96225-96-6)

Safety Data

• Hazardous Substances Data: 96225-96-6(Hazardous Substances Data)

Usage

Uses

6-(4-Methyl-1-piperazinyl)-4-pyrimidinamine is a MNK1/2 inhibitor which makes it effective in cancer therapies.

InChI:InChI=1/C9H15N5/c1-13-2-4-14(5-3-13)9-6-8(10)11-7-12-9/h6-7H,2-5H2,1H3,(H2,10,11,12)

Upstream product

• 109-01-3 1-methyl-piperazine 
• 5305-59-9 4-amino-6-chloropyrimidine 

Relevant articles and documents

Design, synthesis and biological evaluation of pyridone–aminal derivatives as MNK1/2 inhibitors

Excessive phosphorylation of eukaryotic translation initiation factor 4E (eIF4E) plays a major role in the dysregulation of mRNA translation and the activation of tumor cell signaling. eIF4E is exclusively phosphorylated by mitogen-activated protein kinase interacting kinases 1 and 2 (MNK1/2) on Ser209. So, MNK1/2 inhibitors could decrease the level of p-eIF4E and regulate tumor-associated signaling pathways. A series of pyridone–aminal derivatives were synthesized and evaluated as MNK1/2 inhibitors. Several compounds exhibited great inhibitory activity against MNK1/2 and selected compounds showed moderate to excellent anti-proliferative potency against hematologic cancer cell lines. In particular, compound 42i (MNK1 IC50 = 7.0 nM; MNK2 IC50 = 6.1 nM) proved to be the most potent compound against TMD-8 cell line with IC50 value of 0.91 μM. Furthermore, 42i could block the phosphorylation level of eIF4E in CT-26 cell line, and 42i inhibited the tumor growth of CT-26 allograft model significantly. These results indicated that compound 42i was a promising MNK1/2 inhibitor for the potent treatment of colon cancer.

Development of Multifunctional Pyrimidinylthiourea Derivatives as Potential Anti-Alzheimer Agents

Starting from a screening-hit compound, via structure modifications and optimizations, a series of nonfused and nonassembly pyrimidinylthiourea derivatives (2-5) was designed, synthesized, and evaluated as novel multifunctional agents against Alzheimer's disease. Biological activity results demonstrated that compounds 5r and 5t exhibited potent inhibition and excellent selectivity toward acetylcholinesterase (AChE, 5r, IC50 = 0.204 μM, SI > 196; 5t, IC50 = 0.067 μM, SI > 597), specific metal-chelating ability, significant antioxidant effects, modulation of metal-induced Aβ aggregation, inhibition of ROS production by copper redox cycle, low cytotoxicity, and moderate neuroprotection to human neuroblastoma SH-SY5Y cells. Moreover, compound 5r displayed appropriate blood-brain barrier (BBB) permeability both in vitro and in vivo and could improve memory and cognitive function of scopolamine-induced amnesia mice. The multifunctional profiles of 5r and its effectivity in AD mice highlight these structurally distinct pyrimidinylthiourea derivatives as prospective prototypes in the research of innovative multifunctional drugs for Alzheimer's disease.