2-indol-3-yl-3-phenyl-acrylonitrile | 54474-73-6

• 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: 2-indol-3-yl-3-phenyl-acrylonitrile
• 英文别名: 2-(1H-indol-3-yl)-3-phenylacrylonitrile；2-1H-indol-3-yl-3-phenylacrylonitrile；2-(1H-indol-3-yl)-3-phenylprop-2-enenitrile
• CAS: 54474-73-6
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: NABLVJKVDBRRRX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  19
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  39.6
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  2-indol-3-yl-3-phenyl-acrylonitrile 在 碘 作用下， 以 乙醇 为溶剂， 反应 44.0h， 以71%的产率得到11H-benzo[a]carbazole-6-carbonitrile
  参考文献：
  名称：

  Further investigation of Paprotrain: Towards the conception of selective and multi-targeted CNS kinase inhibitors

  摘要：

  Starting from a known compound, identified as the first inhibitor of the kinesin MKLP-2 and named Paprotrain, we have investigated its reactivity to produce through photochemistry a potent nanomolar inhibitor of the kinase DYRK1A.Using similar and different chemical pathways, we have designed several families of compounds that have been screened on a panel of five protein kinases: CK1 delta/epsilon, CDK5/p25, GSK3 alpha/beta, DYRKIA and CLK1, all involved in neurodegenerative disorders such as Alzheimer's disease.We have identified a first group of multi-targeted compounds, a second group of dual inhibitors of DYRKIA & CLK1 and a last group of selective inhibitors of CLK1.Then, our best submicromolar to nanomolar inhibitors were evaluated towards the closest members of the aforementioned kinases: DYRK1B and CLK4, as well as the subfamily CLK2-3.Several compounds appear to be particularly promising for the development of tools in the battle against Alzheimer's disease. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.08.069
• 作为产物：
  描述：

  吲哚-3-乙腈 、 苯甲醛 在 sodium methylate 、 molecular sieve 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 17.0h， 以44%的产率得到2-indol-3-yl-3-phenyl-acrylonitrile
  参考文献：
  名称：

  [EN] AZEPINOINDOLE AND PYRIDOINDOLE DERIVATIVES AS PHARMACEUTICAL AGENTS
  [FR] DERIVES D'AZEPINOINDOLE ET DE PYRIDOINDOLE UTILISES COMME AGENTS PHARMACEUTIQUES

  摘要：

  本发明涉及化合物的公式（I）和公式（II）：公式（I）和（II），其中R1-R8，A和n如描述中所述。这些化合物用于制备药物组合物，并用于调节孤儿核受体的活性的方法。

  公开号：

  WO2003099821A1
• 作为试剂：
  描述：

  吲哚-3-乙腈 、 甲醇 、 苯甲醛 、 sodium methylate 在 2-indol-3-yl-3-phenyl-acrylonitrile 、 氮气 、 氯化铵 、 Sodium sulfate-III 、 crude material 、 SiO2 、 正己烷 、 乙酸乙酯 作用下， 以 二氯甲烷 为溶剂， 反应 17.0h， 以to yield 1.4 g (44% yield) of 2-1H-indol-3-yl-3-phenyl-acrylonitrile的产率得到2-indol-3-yl-3-phenyl-acrylonitrile
  参考文献：
  名称：

  Azepinoindole and pyridoindole derivatives as pharmaceutical agents

  摘要：

  提供了调节受体活性的化合物、组合物和方法。特别地，提供了用于调节受体活性和治疗、预防或缓解与受体活性直接或间接相关的一种或多种疾病或障碍的症状的化合物和组合物。

  公开号：

  US07485634B2

文献信息

• Azepinoindole derivatives as pharmaceutical agents
  申请人：Busch Brett

  公开号：US20050054634A1

  公开（公告）日：2005-03-10

  Compounds, compositions and methods for modulating the activity of receptors are provided. In particular, compounds and compositions are provided for modulating the activity of receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder directly or indirectly related to the activity of the receptors.

  提供了调节受体活性的化合物、组合物和方法。特别地，提供了调节受体活性的化合物和组合物，以及用于治疗、预防或改善与受体活性直接或间接相关的一种或多种疾病或障碍的症状的方法。
• Azepinoindole and Pyridoindole Derivatives as Pharmaceutical Agents
  申请人：Martin Richard

  公开号：US20090326218A1

  公开（公告）日：2009-12-31

  Compounds, compositions and methods for modulating the activity of receptors are provided. In particular compounds and compositions are provided for modulating the activity of receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder directly or indirectly related to the activity of the receptors.

  本发明提供了用于调节受体活性的化合物、组合物和方法。特别提供了用于调节受体活性的化合物和组合物，以及用于治疗、预防或缓解与受体活性直接或间接相关的一种或多种疾病或障碍的症状的方法。
• Azepinoindole Derivatives As Pharmaceutical Agents
  申请人：Busch Brett

  公开号：US20100173824A1

  公开（公告）日：2010-07-08

  Compounds, compositions and methods for modulating the activity of receptors are provided. In particular, compounds and compositions are provided for modulating the activity of receptors and for the treatment, prevention, or amelioration of one or more symptoms of disease or disorder directly or indirectly related to the activity of the receptors.

  本文提供了调节受体活性的化合物、组合物和方法。特别地，提供了用于调节受体活性以及治疗、预防或改善与受体活性直接或间接相关的一种或多种疾病或障碍症状的化合物和组合物。
• [EN] AZEPINOINDOLE AND PYRIDOINDOLE DERIVATIVES AS PHARMACEUTICAL AGENTS<br/>[FR] DERIVES D'AZEPINOINDOLE ET DE PYRIDOINDOLE UTILISES COMME AGENTS PHARMACEUTIQUES
  申请人：X CEPTOR THERAPEUTICS INC

  公开号：WO2003099821A1

  公开（公告）日：2003-12-04

  The present invention is directed to compounds of formula (I) and formula (II): formula (I) and (II), wherein R1-R8, A and n are as described in the description. These compounds are used in pharmaceutical compositions and methods for modulating the activity of orphan nuclear receptors.

  本发明涉及化合物的公式（I）和公式（II）：公式（I）和（II），其中R1-R8，A和n如描述中所述。这些化合物用于制备药物组合物，并用于调节孤儿核受体的活性的方法。
• Further investigation of Paprotrain: Towards the conception of selective and multi-targeted CNS kinase inhibitors
  作者：Christophe Labrière、Olivier Lozach、Mélina Blairvacq、Laurent Meijer、Catherine Guillou

  DOI：10.1016/j.ejmech.2016.08.069

  日期：2016.11

  Starting from a known compound, identified as the first inhibitor of the kinesin MKLP-2 and named Paprotrain, we have investigated its reactivity to produce through photochemistry a potent nanomolar inhibitor of the kinase DYRK1A.Using similar and different chemical pathways, we have designed several families of compounds that have been screened on a panel of five protein kinases: CK1 delta/epsilon, CDK5/p25, GSK3 alpha/beta, DYRKIA and CLK1, all involved in neurodegenerative disorders such as Alzheimer's disease.We have identified a first group of multi-targeted compounds, a second group of dual inhibitors of DYRKIA & CLK1 and a last group of selective inhibitors of CLK1.Then, our best submicromolar to nanomolar inhibitors were evaluated towards the closest members of the aforementioned kinases: DYRK1B and CLK4, as well as the subfamily CLK2-3.Several compounds appear to be particularly promising for the development of tools in the battle against Alzheimer's disease. (C) 2016 Elsevier Masson SAS. All rights reserved.