14-bromo-8,18-diazatetracyclo[9.7.0.02,7.012,17]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one

• ChemBase编号: 153739
• 分子式: C16H11BrN2O
• 平均质量: 327.17534
• 单一同位素质量: 326.00547498
• SMILES: c1ccc2c(c1)c1c(c3cc(ccc3[nH]1)Br)CC(=O)N2
• Canonical SMILES: O=C1Nc2ccccc2c2c(C1)c1cc(Br)ccc1[nH]2
• InChI: InChI=1S/C16H11BrN2O/c17-9-5-6-14-11(7-9)12-8-15(20)18-13-4-2-1-3-10(13)16(12)19-14/h1-7,19H,8H2,(H,18,20)
• InChIKey: QQUXFYAWXPMDOE-UHFFFAOYSA-N

名称和登记号

名称

• IUPAC标准名: 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one; 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one
• IUPAC传统名: 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2,4,6,12,14,16-heptaen-9-one; 14-bromo-8,18-diazatetracyclo[9.7.0.0^2,^7.0^1^2,^1^7]octadeca-1(11),2(7),3,5,12,14,16-heptaen-9-one
• 别名: 9-Bromo-7,12-dihydro-indolo-[3,2-d]-[1]benzazepin-6(5H)-one; NSC 664704; Kenpaullone; 9-Bromo-7,12-dihydroindolo[3,2-d][1]benzazepin-6(5H)-one; 9-Bromopaullone; Kenpaullone

登记号

• CAS号: 142273-20-9
• MDL号: MFCD02683595
• PubChem SID: 24278507; 162247878
• PubChem CID: 3820

理论计算性质

• Acid pKa: 12.954072
• 质子受体: 1
• 质子供体: 2
• LogD (pH = 5.5): 3.5067914
• LogD (pH = 7.4): 3.5067902
• Log P: 3.5067914
• 摩尔折射率: 83.3079 cm^3
• 极化性: 33.262077 Å^3
• 极化表面积: 44.89 Å^2
• 可自由旋转的化学键: 0
• 里宾斯基五规则: true

分子性质

理化性质

• 溶解度: DMSO; DMSO: soluble18 mg/mL, clear, yellow; Ethyl Acetate
• 外观: Dark Yellow Solid; yellow
• 熔点: >300°C (dec.)

安全信息

• 保存条件: -20°C Freezer
• 欧盟危险性物质标志: 刺激性(Irritant) (Xi)
• 德国WGK号: 3
• 危险公开号: 36/37/38
• 安全公开号: 26-36
• GHS危险品标识: GHS07
• GHS警示词: Warning
• GHS危险声明: H315-H319-H335
• GHS警示性声明: P261-P305 + P351 + P338
• 个人保护装置: dust mask type N95 (US), Eyeshields, Gloves
• 保存温度: 2-8°C

药理学性质

• 相关基因信息: human ... CDC2(983)mouse ... Gsk3b(56637)rat ... Gsk3b(84027)

产品相关信息

• 纯度: ≥99%
• Empirical Formula (Hill Notation): C16H11BrN2O

详细说明

Sigma Aldrich - K3888

Biochem/physiol Actions
Kenpaullone is a potent inhibitor of CDK1/cyclin B (IC50 = 400 nM), CDK2/cyclin A (IC50 = 680 nM), CDK2/cyclin E (IC50 = 7.5 uM) and CDK5/p25 (IC50 = 850 nM).
包装
Store under argon

Toronto Research Chemicals - K162500

The paullones are a novel class of kinase inhibitors, initially identified as CDK inhibitors. Kenpaullone has been found to be a useful GSK-3β inhibitor (IC50=23nM).

参考文献

• Zaharevitz, D.W., et al.: Cancer Res., 59, 2566 (1999)
• Leclerc, S., et al.: J. Biol. Chem., 276, 251 (1999)
• Bain, J., et al.: Biochem. J., in press.