2-N-(2-{[4-(2,4-dichlorophenyl)-5-(1H-imidazol-2-yl)pyrimidin-2-yl]amino}ethyl)-5-nitropyridine-2,6-diamine

• ChemBase ID: 164042
• Molecular Formular: C20H17Cl2N9O2
• Molecular Mass: 486.31408
• Monoisotopic Mass: 485.08822619
• SMILES: c1(c(nc(nc1)NCCNc1ccc(c(n1)N)[N+](=O)[O-])c1ccc(cc1Cl)Cl)c1[nH]ccn1
• Canonical SMILES: Clc1ccc(c(c1)Cl)c1nc(NCCNc2ccc(c(n2)N)[N+](=O)[O-])ncc1c1ncc[nH]1
• InChI: InChI=1S/C20H17Cl2N9O2/c21-11-1-2-12(14(22)9-11)17-13(19-25-6-7-26-19)10-28-20(30-17)27-8-5-24-16-4-3-15(31(32)33)18(23)29-16/h1-4,6-7,9-10H,5,8H2,(H,25,26)(H3,23,24,29)(H,27,28,30)
• InChIKey: NDFXSHIIGXVOKT-UHFFFAOYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-N-(2-{[4-(2,4-dichlorophenyl)-5-(1H-imidazol-2-yl)pyrimidin-2-yl]amino}ethyl)-5-nitropyridine-2,6-diamine
• IUPAC Traditional name: 2-N-(2-{[4-(2,4-dichlorophenyl)-5-(1H-imidazol-2-yl)pyrimidin-2-yl]amino}ethyl)-5-nitropyridine-2,6-diamine
• Synonyms: N6-[2-[[4-(2,4-Dichlorophenyl)-5-(1H-imidazol-2-yl)-2-pyrimidinyl]amino]ethyl]-3-nitro-2,6-pyridinediamine; CHIR-98014

Database IDs

• CAS Number: 556813-39-9
• PubChem SID: 162258177
• PubChem CID: 9957049

CALCULATED PROPERTIES

• Acid pKa: 12.213838
• H Acceptors: 9
• H Donor: 4
• LogD (pH = 5.5): 3.8440044
• LogD (pH = 7.4): 4.342117
• Log P: 4.3555646
• Molar Refractivity: 140.0703 cm^3
• Polarizability: 48.045517 Å^3
• Polar Surface Area: 163.25 Å^2
• Rotatable Bonds: 8
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Yellow Solid
• Melting Point: 192-196°C

Safety Information

• Storage Condition: Refrigerator

DETAILS

Toronto Research Chemicals - C292100

A glycogen synthase kinase-3 (GSK-3) inhibitor. Effects of GSK inhibitors on p-tau, GSK-3β activities and cell death were measured in a human neuronal cell line (LUHMES). Lithium and CHIR98014 reduced tau phosphorylation (Ser396) in the cortex and hippoca

REFERENCES

• Aardema, M., et al.: Mutat. Res., 410, 3 (1998)
• Coghlan, M., et al.: Chem. Biol., 7, 793 (1998)
• Ring, D., et al.: Diabetes, 52, 588 (1998)
• Ougolkov, A., et al.: Cancer Res., 65, 2076 (1998)
• Armstrong, V., et al.: J. Biol. Chem., 282, 20715 (1998)
• Guo