3-(3-oxo-2,3-dihydro-1H-indol-2-ylidene)-2,3-dihydro-1H-indol-2-one

• ChemBase编号: 73010
• 分子式: C16H10N2O2
• 平均质量: 262.2628
• 单一同位素质量: 262.07422757
• SMILES: c1ccc2c(c1)NC(=O)/C/2=C\1/Nc2c(C1=O)cccc2
• Canonical SMILES: O=C1/C(=C/2\C(=O)Nc3c2cccc3)/Nc2c1cccc2
• InChI: InChI=1S/C16H10N2O2/c19-15-10-6-2-4-8-12(10)17-14(15)13-9-5-1-3-7-11(9)18-16(13)20/h1-8,17H,(H,18,20)/b14-13+
• InChIKey: CRDNMYFJWFXOCH-BUHFOSPRSA-N

名称和登记号

名称

• IUPAC标准名: 3-(3-oxo-2,3-dihydro-1H-indol-2-ylidene)-2,3-dihydro-1H-indol-2-one
• IUPAC传统名: 3-(3-oxo-1H-indol-2-ylidene)-1H-indol-2-one
• 别名: Indirubin

登记号

• CAS号: 479-41-4
• PubChem SID: 162037930
• PubChem CID: 5359405

理论计算性质

• Acid pKa: 7.41985
• 质子受体: 3
• 质子供体: 2
• LogD (pH = 5.5): 2.429935
• LogD (pH = 7.4): 2.1638434
• Log P: 2.434867
• 摩尔折射率: 78.9954 cm^3
• 极化性: 28.034647 Å^3
• 极化表面积: 58.2 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

安全信息

• 保存条件: -20°C

药理学性质

• 作用靶点: GSK-3

产品相关信息

• 成盐信息: Free Base

详细说明

Selleck Chemicals - S2386

Research Area: Cancer
Biological Activity:
Indirubin is a potent cyclin-dependent kinases and GSK-3β inhibitor with IC50 of about 75 nM and 0.19 μM. It inhibits CDK5- and GSK-3β-mediated tau phosphorylation, a process over-active in Alzheimer disease states. Also inhibits AMPK, LCK and SGK. Induces cell cycle arrest and inhibits cell proliferation. It suppressed tumor necrosis factor (TNF)-induced NF-κB activation in a dose- and time-dependent manner. Indirubin also suppressed the NF-κB activation induced by various inflammatory agents and carcinogens. Further studies showed that indirubin blocked the phosphorylation and degradation of IκBα through the inhibition of activation of IκBα kinase and phosphorylation and nuclear translocation of p65. NF-κB reporter activity induced by TNFR1, TNF receptor-associated death domain, TRAF2, TAK1, NF-κB-inducing kinase, and IKKβ was inhibited by indirubin but not that induced by p65 transfection. [1][2]References on Indirubin[1] NATURE CELL BIOLOGY, MAY 1999, 1：60－67[2] THE JOURNAL OF BIOLOGICAL CHEMISTRY, 2001, 276：251–260

参考文献

• Hoessel R et al. Nat Cell Biol. 1999 May;1(1):60-7.