(4-bromophenyl)(1,2,3,4-tetrahydro-β-carbolin-2-yl)methanone | 571154-13-7

• 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: (4-bromophenyl)(1,2,3,4-tetrahydro-β-carbolin-2-yl)methanone
• 英文别名: (4-Bromophenyl)-(1,3,4,9-tetrahydropyrido[3,4-b]indol-2-yl)methanone
• CAS: 571154-13-7
• 化学式: C₁₈H₁₅BrN₂O
• 分子量: 355.234
• InChiKey: XIRVNUWCOWVCQT-UHFFFAOYSA-N

物化性质

• 熔点：
  217 °C
• 沸点：
  552.8±50.0 °C(Predicted)
• 密度：
  1.524±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  22
• 可旋转键数：
  1
• 环数：
  4.0
• 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：

  (4-bromophenyl)(1,2,3,4-tetrahydro-β-carbolin-2-yl)methanone 、 3-氟苯基硼酸 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84%的产率得到(3,4-Dihydro-1H-pyrido[3,4-b]indol-2(9H)-yl)(3''-fluorobiphenyl-4-yl)methanone
  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：

  1,2,3,4-四氢-9H-吡啶[3,4-B]并吲哚 、 4-溴苯甲酰氯 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 反应 3.08h， 以62%的产率得到(4-bromophenyl)(1,2,3,4-tetrahydro-β-carbolin-2-yl)methanone
  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。
• [EN] FASCAPLYSIN DERIVATIVES AND THEIR USE IN THE TREATMENT OF CANCER<br/>[FR] DÉRIVÉS DE FASCAPLYSINE ET LEUR UTILISATION DANS LE TRAITEMENT D'UN CANCER
  申请人：UNIV MONTFORT

  公开号：WO2009022104A1

  公开（公告）日：2009-02-19

  A method of treating cancer comprising administering a compound of Formula (I), (II) or (III) to a patient.

  一种治疗癌症的方法，包括向患者给予化合物I、II或III的剂量。
• 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.