CA238 | 883560-98-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: CA238
• 英文别名: 4-bromo-N-[2-(1H-indol-3-yl)ethyl]-N-methylbenzamide；N-(2-(1H-indol-3-yl)ethyl)-4-bromo-N-methylbenzamide
• CAS: 883560-98-3
• 化学式: C₁₈H₁₇BrN₂O
• 分子量: 357.25
• InChiKey: GKWRNEOLDXGCRU-UHFFFAOYSA-N

物化性质

• 熔点：
  160 °C
• 沸点：
  559.0±40.0 °C(Predicted)
• 密度：
  1.425±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  22
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  36.1
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  CA238 、 4-叔丁基苯硼酸 在 四(三苯基膦)钯 potassium carbonate 作用下， 以 乙醇 、 甲苯 为溶剂， 反应 24.0h， 以51%的产率得到N-(2-(1H-Indol-3-yl)ethyl)-4''-tert-butyl-N-methylbiphenyl-4-carboxamide
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4

  摘要：

  We present the design, synthesis and biological activity of a library of substituted (biphenylcarbonyl)-tryptamine and ( biphenylcarbonyl)-tetrahydro-beta-carboline compounds related to the natural product fascaplysin, as novel inhibitors of CDK4/cyclin D1. We show all these molecules, prepared using the Suzuki-Miyaura reaction, being selective inhibitors of CDK4 over CDK2. The most active compounds have a CDK4 IC50 in the range 9-11 mu M, three of them containing the para-biphenyl plus para-substituents supporting the existence of a pi-stacking pocket within the active site of CDK4. (C) 2008 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmc.2008.07.002
• 作为产物：
  描述：

  ethyl 2-(1H-indole-3-yl)ethylcarbamate 在 sodium hydroxide 、 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 4.08h， 生成 CA238
  参考文献：
  名称：

  Design, synthesis and biological activity of new CDK4-specific inhibitors, based on fascaplysin

  摘要：

  我们介绍了三类色胺衍生物的设计、合成及其生物活性，这些衍生物是非平面型的毒性抗癌剂fascaplysin的类似物。我们表明这些化合物是CDK4相对于CDK2的选择性抑制剂，活性最强的化合物9q对CDK4的抑制作用具有6 µM的IC50值。

  DOI：

  10.1039/b518019h

文献信息

• Design, synthesis and biological activity of new CDK4-specific inhibitors, based on fascaplysin
  作者：Carine Aubry、A. James Wilson、Paul R. Jenkins、Sachin Mahale、Bhabatosh Chaudhuri、Jean-Didier Maréchal、Michael J. Sutcliffe

  DOI：10.1039/b518019h

  日期：——

  We present the design, synthesis, and biological activity of three classes of tryptamine derivatives, which are non-planar analogues of the toxic anti-cancer agent fascaplysin. We show these compounds to be selective inhibitors of CDK4 over CDK2, the most active compound 9q has an IC50 for the inhibition of CDK4 of 6 µM.

  我们介绍了三类色胺衍生物的设计、合成及其生物活性，这些衍生物是非平面型的毒性抗癌剂fascaplysin的类似物。我们表明这些化合物是CDK4相对于CDK2的选择性抑制剂，活性最强的化合物9q对CDK4的抑制作用具有6 µM的IC50值。
• Design, synthesis and biological evaluation of new tryptamine and tetrahydro-β-carboline-based selective inhibitors of CDK4
  作者：Paul R. Jenkins、James Wilson、Daniel Emmerson、Marcos D. Garcia、Matthew R. Smith、Stephen J. Gray、Robert G. Britton、Sachin Mahale、Bhabatosh Chaudhuri

  DOI：10.1016/j.bmc.2008.07.002

  日期：2008.8

  We present the design, synthesis and biological activity of a library of substituted (biphenylcarbonyl)-tryptamine and ( biphenylcarbonyl)-tetrahydro-beta-carboline compounds related to the natural product fascaplysin, as novel inhibitors of CDK4/cyclin D1. We show all these molecules, prepared using the Suzuki-Miyaura reaction, being selective inhibitors of CDK4 over CDK2. The most active compounds have a CDK4 IC50 in the range 9-11 mu M, three of them containing the para-biphenyl plus para-substituents supporting the existence of a pi-stacking pocket within the active site of CDK4. (C) 2008 Published by Elsevier Ltd.