252935-94-7

Basic information

• Product Name: 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-
• Synonyms: 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-;N6-[ 2-[4-(2,4-DICHLORO-PHENYL)-5-IMIDAZOL-1-YL-PYRIMIDIN-2-YLAMINO]-ETHYL]-3-NITRO-PYRIDINE-2,6-DIAMINE;CHIR98014(CT98014);N2-(2-((4-(2,4-dichlorophenyl)-5-(1H-iMidazol-1-yl)pyriMidin-2-yl)aMino)ethyl)-5-nitropyridine-2,6-diaMine;N6-[2-[[4-(2,4-Dichlorophenyl)-5-(1H-imidazol-1-yl)-2-pyrimidinyl]amino]ethyl]-3-nitro-2,6-pyridinediamine;2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-;N6-[2-[[4-(2,4-dichlorophenyl)-5-(1H-imidazol-1-yl)-2-pyrimidinyl]amino]ethyl]-3-nitro-2,6-Pyridinediamine CHIR98014
• CAS NO: 252935-94-7
• Molecular Formula: C20H17Cl2N9O2
• Molecular Weight: 486.31
• Product Categories: PI3K/Akt/mTOR;Inhibitors;Akt;mTOR;PI3K
• Mol File: 252935-94-7.mol

Chemical Properties

• Appearance: /
• Density: 1.62
• Storage Temp.: -20°C
• Solubility: insoluble in H2O; insoluble in EtOH; ≥8.1 mg/mL in DMSO with gentle warming
• CAS DataBase Reference: 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-(CAS DataBase Reference)
• NIST Chemistry Reference: 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-(252935-94-7)
• EPA Substance Registry System: 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITRO-(252935-94-7)

Safety Data

• WGK Germany: 3
• Hazardous Substances Data: 252935-94-7(Hazardous Substances Data)

Usage

Uses

Used in Pharmaceutical Industry:
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITROis used as a pharmaceutical compound for its potential therapeutic effects. The compound's unique structure allows it to interact with specific biological targets, making it a promising candidate for the development of new drugs.
Used in Chemical Research:
In the field of chemical research, 2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITROserves as a valuable compound for studying its chemical properties, reactivity, and potential applications in the synthesis of other complex molecules.
Used in Material Science:
The compound's unique structure and properties make it a candidate for use in material science, where it could be employed in the development of new materials with specific properties, such as improved stability, reactivity, or selectivity.
Used in Chromatin Immunoprecipitation (ChIP) Studies:
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITROcan be used as a Wnt/β-catenin pharmacological agonist in cell-conditioned medium for performing ChIP studies in neurons, such as HT22 neurons. This application allows researchers to investigate the epigenetic regulation of gene expression and the role of Wnt/β-catenin signaling in neuronal function and development.
Used in Neural Progenitor Cell Research:
The compound has been used for the generation of small molecules that promote the differentiation of neural progenitor cells towards motor neurons. This application is crucial for understanding the molecular mechanisms underlying neuronal development and could potentially lead to the development of new therapeutic strategies for neurological disorders.

Biological Activity

chir-98014 is a potent inhibitor of gsk-3α and gsk-3β with ic50 values of 0.65 nm and 0.58 nm, respectively [1]gsk-3 (glycogen synthase kinase 3) is a serine/threonine protein kinase and plays a pivotal role in a number of central intracellular signaling pathways, including cellular proliferation, migration, inflammation and immune responses, glucose regulation, and apoptosis. recently, it has been reported that gsk-3 abnormally expressed in a variety of diseases, including type ii diabetes, alzheimer's disease, inflammation, cancer, and bipolar disorder [2, 3].chir-98014 is a potent gsk-3α and gsk-3β inhibitor. when tested with insulin receptor-expressing cho-ir cells or primary rat hepatocytes, chir-98014 stimulated the gs activity ratio as high as two- to three fold compared with basal in a dose dependent manner. similarly, in isolated type 1 skeletal muscle from insulin-sensitive lean zucker and from insulin-resistant zdf rats, administration of chir-98014 activated gs activity ratio [1]. in mouse es-d3 cells, chir-98014 treatment (48 and 72 hours later) resulted in a significant activation of the wnt/beta-catenin pathway via inhibiting gsk-3 [4].in markedly diabetic and insulin-resistant db/db mice model, oral administration of chir-98014 (30mg/kg) significantly reduced fasting hyperglycemia within 4 hours and improved glucose disposal during an ipgtt [1].

Biochem/physiol Actions

CHIR 98014 is a glycogen synthase kinase-3 (GSK-3) inhibitor with IC50 values of 0.65 nM and 0.58 nM for GSK3α and GSK3β, respectively. CHIR98014 is 500-fold to >10,000-fold selectivity for GSK-3 versus 20 other protein kinases tested, including closest homologs Cdc2 and ERK2.

references

[1]. ring, d.b., et al., selective glycogen synthase kinase 3 inhibitors potentiate insulin activation of glucose transport and utilization in vitro and in vivo. diabetes, 2003. 52(3): p. 588-95.[2]. pan wa, et al. the rna recognition motif of nifk is required for rrna maturation during cell cycle progression. rna biol. 2015. 12(3):255-67.[3]. mccubrey ja, et al. gsk-3 as potential target for therapeutic intervention in cancer. oncotarget. 2014. 5(10):2881-911.[4]. naujok o, et al. cytotoxicity and activation of the wnt/beta-catenin pathway in mouse embryonic stem cells treated with four gsk3 inhibitors. bmc res notes. 2014. 7(1):273-281.

Upstream product

• 4252-78-2 2,2',4'-trichloroacetophenone 
• 46503-52-0 1-(2,4-dichlorophenyl)-2-(imidazol-1-yl)ethanone 
• 82013-34-1 1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-imidazolylprop-2-en-1-one 

Relevant articles and documents

Synthesis, Binding Mode, and Antihyperglycemic Activity of Potent and Selective (5-Imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine Inhibitors of Glycogen Synthase Kinase 3

In an effort to identify new antidiabetic agents, we have discovered a novel family of (5-imidazol-2-yl-4-phenylpyrimidin-2-yl)[2-(2-pyridylamino)ethyl]amine analogues which are inhibitors of human glycogen synthase kinase 3 (GSK3). We developed efficient synthetic routes to explore a wide variety of substitution patterns and convergently access a diverse array of analogues. Compound 1 (CHIR-911, CT-99021, or CHIR-73911) emerged from an exploration of heterocycles at the C-5 position, phenyl groups at C-4, and a variety of differently substituted linker and aminopyridine moieties attached at the C-2 position. These compounds exhibited GSK3 IC50s in the low nanomolar range and excellent selectivity. They activate glycogen synthase in insulin receptor-expressing CHO-IR cells and primary rat hepatocytes. Evaluation of lead compounds 1 and 2 (CHIR-611 or CT-98014) in rodent models of type 2 diabetes revealed that single oral doses lowered hyperglycemia within 60 min, enhanced insulin-stimulated glucose transport, and improved glucose disposal without increasing insulin levels.

Inhibitors of glycogen synthase kinase 3

New pyrimidine or pyridine based compounds, compositions and methods of inhibiting the activity of glycogen synthase kinase (GSK3) in vitro and of treatment of GSK3 mediated disorders in vivo are provided. The methods, compounds and compositions of the invention may be employed alone, or in combination with other pharmacologically active agents in the treatment of disorders mediated by GSK3 activity, such as diabetes, Alzheimer's disease and other neurodegenerative disorders, obesity, atherosclerotic cardiovascular disease, essential hypertension, polycystic ovary syndrome, syndrome X, ischemia, traumatic brain injury, bipolar disorder, immunodeficiency or cancer.

Inhibitors of glycogen synthase kinase 3

Novel pyridine and pyrimidine derivatives which selectively inhibit glycogen synthase kinase 3 are provided and methods of preparing these compounds are provided. These compounds are useful in treating certain conditions which may be mediated by glycogen synthase kinase 3.