5-[N-(2-dimethylaminoethyl)aminocarbonyl]indirubin | 1238056-97-7

• 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: 5-[N-(2-dimethylaminoethyl)aminocarbonyl]indirubin
• 英文别名: N-[2-(dimethylamino)ethyl]-2-oxo-3-(3-oxo-1H-indol-2-ylidene)-1H-indole-5-carboxamide
• CAS: 1238056-97-7
• 化学式: C₂₁H₂₀N₄O₃
• 分子量: 376.415
• InChiKey: HYLHQILTRYTGBH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.95
• 重原子数：
  28.0
• 可旋转键数：
  4.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  90.54
• 氢给体数：
  3.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5-[N-(2-dimethylaminoethyl)aminocarbonyl]indirubin 、 硫酸二甲酯 以 5,5-dimethyl-1,3-cyclohexadiene 、 硝基苯 为溶剂， 反应 0.75h， 以82%的产率得到2-(indirubin-5-carbonylamino)-ethyl-trimethyl-ammonium methosulfate
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel indirubin-5-carboxamides

  摘要：

  Indirubins have been reported to act as potent inhibitors of protein kinases relevant to tumorigenesis and of tumor cell growth, but their development to antitumor drugs suffer from their poor water solubility. We synthesized a novel class of indirubin derivatives, indirubin-5-carboxamides, carrying amide substituents with basic centers. Quaternization or protonation of these alkylamino substituents provided indirubins with significantly improved solubility without loss of bioactivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.066
• 作为产物：
  描述：

  pentafluorophenyl indirubin-5-carboxylate 、 N,N-二甲基乙二胺 在 4-二甲氨基吡啶 作用下， 以 1,4-二氧六环 为溶剂， 以88%的产率得到5-[N-(2-dimethylaminoethyl)aminocarbonyl]indirubin
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel indirubin-5-carboxamides

  摘要：

  Indirubins have been reported to act as potent inhibitors of protein kinases relevant to tumorigenesis and of tumor cell growth, but their development to antitumor drugs suffer from their poor water solubility. We synthesized a novel class of indirubin derivatives, indirubin-5-carboxamides, carrying amide substituents with basic centers. Quaternization or protonation of these alkylamino substituents provided indirubins with significantly improved solubility without loss of bioactivity. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.04.066