3-(2-cyanoacetyl)-1H-indole-5-carbonitrile | 1589071-17-9

• 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-(2-cyanoacetyl)-1H-indole-5-carbonitrile
• CAS: 1589071-17-9
• 化学式: C₁₂H₇N₃O
• 分子量: 209.207
• InChiKey: JZNZZUQOMOIYDM-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  16
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.08
• 拓扑面积：
  80.4
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  3-吲哚甲醛 、 3-(2-cyanoacetyl)-1H-indole-5-carbonitrile 在 potassium hydroxide 作用下， 以 乙醇 为溶剂， 生成 3-(2-cyano-3-(1H-indol-3-yl)acryloyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Multisubstituted indole–acrylonitrile hybrids as potential cytotoxic agents

  摘要：

  A series of multisubstituted indole-acrylonitrile hybrids were designed, synthesized and evaluated for their potential cytotoxic activities. The bio-evaluation results indicated that some of the target compounds (such as 3a, 3f, 3k, 3n) exhibited good to moderate cytotoxic effect on HepG2, BCG-823, BEL7402, and HL-7702 cell lines. Especially, the compounds 3a and 3k also exhibited high cytotoxic activities (3a, 19.38 +/- 3.38 mu M; 3k, 15.43 +/- 3.54 mu M) against the BEL-7402 cell line resistant to Taxol (>25 mu M) and 5-FU (>500 mu M), which might be developed as novel lead scaffold for potential anticancer agents. (c) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.03.011
• 作为产物：
  描述：

  5-氰基吲哚 、 氰乙酸 以 乙酸酐 为溶剂， 反应 0.08h， 生成 3-(2-cyanoacetyl)-1H-indole-5-carbonitrile
  参考文献：
  名称：

  Synthesis and Biological Evaluation of Indolyl Bis-chalcones as Anti-Breast Cancer and Antioxidant Agents

  摘要：

  DOI：

  10.5562/cca3758

文献信息

• Iodine-catalyzed oxidative annulation of 3-cyanoacetylindoles with benzylamines: facile access to 5-(3-indolyl)oxazoles
  作者：Xiaozu Liu、Yuxiang Zhou、Guojun Chen、Zhongqin Yang、Qin Li、Peijun Liu

  DOI：10.1039/c8ob00833g

  日期：——

  An iodine-catalyzed oxidative annulation of 3-cyanoacetylindoles with benzylamines has been developed. This reaction enables the convenient synthesis of a variety of 5-(3-indolyl)oxazoles under mild conditions with broad functional group compatibility.

  已经开发了碘催化的3-氰基乙酰吲哚与苄胺的氧化环合反应。该反应使得在温和条件下具有广泛的官能团相容性的各种5-（3-吲哚基）恶唑的方便合成成为可能。