N-(2,2-dimethoxyethyl)-5-nitro-1H-indole-2-carboxamide | 1189035-78-6

• 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: N-(2,2-dimethoxyethyl)-5-nitro-1H-indole-2-carboxamide
• 英文别名: 5-nitro-1H-indole-2-carboxylic acid (2,2-dimethoxyethyl)amide；5-nitro-1H-indole-2-carboxylic acid (2,2-dimethoxy-ethyl)-amide
• CAS: 1189035-78-6
• 化学式: C₁₃H₁₅N₃O₅
• 分子量: 293.279
• InChiKey: GSMHQIGSTGUVLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  109
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-(2,2-dimethoxyethyl)-5-nitro-1H-indole-2-carboxamide 在 polyphosphoric acid(PPA) 作用下， 反应 0.5h， 以93%的产率得到6-nitro-2,9-dihydro-1H-pyrido[3,4-b]indol-1-one
  参考文献：
  名称：

  A New, Simple, and High-Yielding Synthesis of 2,9-Dihydro-1H-pyrido[3,4-b]indol-1-ones

  摘要：

  A new, simple, and high-yielding method was developed to prepare 2,9-dihydro-1H-pyrido[3,4-b]indol-1-ones by selective cyclization of the appropriate N-(2,2-dimethoxyethyl)-1H-indole-2-carboxamide in polyphosphoric acid at 110 degrees C for 30 minutes. The reaction yield was strongly dependent on the acid used. The method was less affected by the presence of electron-donating and -withdrawing substituents at 5-position of the indole nucleus.

  DOI：

  10.1055/s-0033-1339155
• 作为产物：
  描述：

  5-硝基吲哚-2-甲酸 、 氨基乙醛缩二甲醇 在 氯化亚砜 、 碳酸氢钠 作用下， 以 1,4-二氧六环 、 四氢呋喃 、 水 为溶剂， 反应 2.0h， 以90%的产率得到N-(2,2-dimethoxyethyl)-5-nitro-1H-indole-2-carboxamide
  参考文献：
  名称：

  [EN] 3,4-DIHYDRO-2H-PYRAZINO[1,2-A]INDOL-1-ONE DERIVATIVES ACTIVE AS KINASE INHIBITORS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  [FR] DÉRIVÉS ACTIFS DE 3,4-DIHYDRO-2H-PYRAZINO[1,2-A]INDOL-1-ONE EN TANT QU'INHIBITEURS DE KINASE, PROCÉDÉ POUR LEUR PRÉPARATION ET COMPOSITIONS PHARMACEUTIQUES LES CONTENANT

  摘要：

  公开号：

  WO2009118411A3

文献信息

• 3,4-DIHYDRO-2H-PYRAZINO[1,2-A]INDOL-1-ONE DERIVATIVES ACTIVE AS KINASE INHIBITORS, PROCESS FOR THEIR PREPARATION AND PHARMACEUTICAL COMPOSITIONS COMPRISING THEM
  申请人：Cervi Giovanni

  公开号：US20110183971A1

  公开（公告）日：2011-07-28

  Compounds which are 3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one derivatives or pharmaceutically acceptable salts thereof, their preparation process and pharmaceutical compositions comprising them are disclosed; these compounds are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, viral infection, prevention of AIDS development in HIV-infected individuals, cell proliferative disorders, autoimmune and neurodegenerative disorders; also disclosed is a process under Solid Phase Synthesis conditions for preparing the compounds of the invention and chemical libraries comprising a plurality of them.

  本发明公开了3,4-二氢-2H-吡唑并[1,2-a]吲哚-1-酮衍生物或其药学上可接受的盐，其制备过程以及包含它们的制药组合物；这些化合物在治疗由改变的蛋白激酶活性引起和/或相关的疾病方面具有用途，如癌症、病毒感染、预防HIV感染者艾滋病的发展、细胞增殖性疾病、自身免疫和神经退行性疾病；本发明还公开了一种在固相合成条件下制备本发明化合物的过程和化学文库，其中包括多种这些化合物。
• 3,4-dihydro-2H-pyrazino[1,2-A]indol-1-one derivatives active as kinase inhibitors, process for their preparation and pharmaceutical compositions comprising them
  申请人：Nerviano Medical Sciences S.R.L.

  公开号：US08207165B2

  公开（公告）日：2012-06-26

  Compounds which are 3,4-dihydro-2H-pyrazino[1,2-a]indol-1-one derivatives or pharmaceutically acceptable salts thereof, their preparation process and pharmaceutical compositions comprising them are disclosed; these compounds are useful in the treatment of diseases caused by and/or associated with an altered protein kinase activity such as cancer, viral infection, prevention of AIDS development in HIV-infected individuals, cell proliferative disorders, autoimmune and neurodegenerative disorders; also disclosed is a process under Solid Phase Synthesis conditions for preparing the compounds of the invention and chemical libraries comprising a plurality of them.

  本文披露了3,4-二氢-2H-吡嗪并[1,2-a]吲哚-1-酮衍生物或其药学上可接受的盐、它们的制备过程以及包含它们的制药组合物；这些化合物可用于治疗由蛋白激酶活性改变引起和/或相关的疾病，例如癌症、病毒感染、预防HIV感染者发展艾滋病、细胞增殖性疾病、自身免疫和神经退行性疾病；本文还披露了一种在固相合成条件下制备本发明化合物的方法以及包含多种这些化合物的化学文库。
• US8207165B2
  申请人：——

  公开号：US8207165B2

  公开（公告）日：2012-06-26
• US8513241B2
  申请人：——

  公开号：US8513241B2

  公开（公告）日：2013-08-20