3-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide | 401461-86-7

• 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: 3-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide
• CAS: 401461-86-7
• 化学式: C₁₇H₁₅BrN₂O
• 分子量: 343.223
• InChiKey: MGSVLADKXFITRZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  44.9
• 氢给体数：
  2
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  3-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide 在 三氟甲磺酸酐 、 三苯基氧化膦 、 manganese(IV) oxide 作用下， 以 氯苯 为溶剂， 反应 4.0h， 以88%的产率得到1-(3-溴苯基)-9H-吡啶[3,4-B]吲哚
  参考文献：
  名称：

  亨德里克森试剂引发的Pictet-Gams反应的替代物：酰胺中的异喹啉和β-咔啉

  摘要：

  衍生自三氟甲磺酸酐和三苯基氧化膦的亨德里克森试剂表现出高的亲氧性，并完美地诱导了β-芳基乙酰胺的分子内环化。因此，开发了一种一锅法访问异喹啉和β-咔啉，该方法涉及环化，然后进行氧化芳构化。 亨德里克森试剂-异喹啉-β-咔啉-β-芳基乙酰胺-氧化锰

  DOI：

  10.1055/s-0029-1217138
• 作为产物：
  描述：

  色胺 、 3-溴苯甲酰氯 在 sodium hydroxide 作用下， 以 二氯甲烷 为溶剂， 以79%的产率得到3-bromo-N-[2-(1H-indol-3-yl)ethyl]benzamide
  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

文献信息

• 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.
• An Alternative to Pictet-Gams Reaction Triggered by Hendrickson Reagent: Isoquinolines and β-Carbolines from Amides
  作者：Shaozhong Wang、Mengde Wu

  DOI：10.1055/s-0029-1217138

  日期：2010.2

  The Hendrickson reagent derived from triflic anhydride and triphenylphosphine oxide exhibited high oxophilicity and induced the intramolecular cyclization of β-arylethylamides perfectly. Thus, a one-pot protocol to access isoquinoline and β-carboline was developed involving cyclization followed by oxidative aromatization. Hendrickson reagent - isoquinoline - β-carboline - β-arylethylamide - manganese(IV)

  衍生自三氟甲磺酸酐和三苯基氧化膦的亨德里克森试剂表现出高的亲氧性，并完美地诱导了β-芳基乙酰胺的分子内环化。因此，开发了一种一锅法访问异喹啉和β-咔啉，该方法涉及环化，然后进行氧化芳构化。 亨德里克森试剂-异喹啉-β-咔啉-β-芳基乙酰胺-氧化锰