2-(1-(prop-2-ynyl)-1H-indol-3-yl)quinoline-3-carbonitrile | 1366500-90-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-(1-(prop-2-ynyl)-1H-indol-3-yl)quinoline-3-carbonitrile
• CAS: 1366500-90-4
• 化学式: C₂₁H₁₃N₃
• 分子量: 307.354
• InChiKey: DZLLBLYUCUFYAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.36
• 重原子数：
  24.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.05
• 拓扑面积：
  41.61
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-(1-(prop-2-ynyl)-1H-indol-3-yl)quinoline-3-carbonitrile 、 N-(2-iodo-4-methylphenyl)methanesulfonamide 在 copper(l) iodide 、 palladium 10% on activated carbon 、 三乙胺 、 三苯基膦 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 2-(1-((1-(methylsulfonyl)-1H-5-methylindol-2-yl)methyl)-1H-indol-3-yl)quinoline-3-carbonitrile
  参考文献：
  名称：

  C–C bond formation at C-2 of a quinoline ring: Synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors

  摘要：

  A number of 2-(1H-indol-3-yl) quinoline-3-carbonitrile derivatives were synthesized via AlCl3-mediated C-C bond forming reaction between 2-chloroquinoline-3-carbonitrile and various indoles. The methodology does not require any N-protection of the indoles employed and provided the corresponding products in good yields. The molecular structure of a representative compound was established unambiguously by single crystal X-ray diffraction and structural elaboration of a compound synthesized has been demonstrated. Many of these compounds synthesized showed PDE4 inhibitory properties in vitro. A brief structure-activity relationship studies within the series along with docking results of a representative compound (EC50 similar to 0.89 mu M) is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.027
• 作为产物：
  描述：

  吲哚 在 aluminum (III) chloride 、 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 1,2-二氯乙烷 、 甲苯 为溶剂， 反应 12.0h， 生成 2-(1-(prop-2-ynyl)-1H-indol-3-yl)quinoline-3-carbonitrile
  参考文献：
  名称：

  C–C bond formation at C-2 of a quinoline ring: Synthesis of 2-(1H-indol-3-yl)quinoline-3-carbonitrile derivatives as a new class of PDE4 inhibitors

  摘要：

  A number of 2-(1H-indol-3-yl) quinoline-3-carbonitrile derivatives were synthesized via AlCl3-mediated C-C bond forming reaction between 2-chloroquinoline-3-carbonitrile and various indoles. The methodology does not require any N-protection of the indoles employed and provided the corresponding products in good yields. The molecular structure of a representative compound was established unambiguously by single crystal X-ray diffraction and structural elaboration of a compound synthesized has been demonstrated. Many of these compounds synthesized showed PDE4 inhibitory properties in vitro. A brief structure-activity relationship studies within the series along with docking results of a representative compound (EC50 similar to 0.89 mu M) is presented. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.02.027