252935-94-7 Usage
Description
2,6-PYRIDINEDIAMINE, N6-[2-[[4-(2,4-DICHLOROPHENYL)-5-(1H-IMIDAZOL-1-YL)-2-PYRIMIDINYL]AMINO]ETHYL]-3-NITROis a complex organic compound with a unique chemical structure. It is characterized by its 2,6-pyridinediamine core, with a nitrogen atom at the 6th position, which is connected to a complex side chain. This side chain includes a 2-pyrimidinyl group, an imidazol-1-yl group, and a 2,4-dichlorophenyl group. The compound also features an ethyl group and a nitro group at the 3rd position. Due to its specific chemical properties and structure, it has potential applications in various fields.
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.
Check Digit Verification of cas no
The CAS Registry Mumber 252935-94-7 includes 9 digits separated into 3 groups by hyphens. The first part of the number,starting from the left, has 6 digits, 2,5,2,9,3 and 5 respectively; the second part has 2 digits, 9 and 4 respectively.
Calculate Digit Verification of CAS Registry Number 252935-94:
(8*2)+(7*5)+(6*2)+(5*9)+(4*3)+(3*5)+(2*9)+(1*4)=157
157 % 10 = 7
So 252935-94-7 is a valid CAS Registry Number.
252935-94-7Relevant 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
Wagman, Allan S.,Boyce, Rustum S.,Brown, Sean P.,Fang, Eric,Goff, Dane,Jansen, Johanna M.,Le, Vincent P.,Levine, Barry H.,Ng, Simon C.,Ni, Zhi-Jie,Nuss, John M.,Pfister, Keith B.,Ramurthy, Savithri,Renhowe, Paul A.,Ring, David B.,Shu, Wei,Subramanian, Sharadha,Zhou, Xiaohui A.,Shafer, Cynthia M.,Harrison, Stephen D.,Johnson, Kirk W.,Bussiere, Dirksen E.
, p. 8482 - 8514 (2017/11/03)
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
-
, (2008/06/13)
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.
