2-(1H-indol-3-yl)quinoline-3-carbonitrile | 1366500-53-9

• 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-(1H-indol-3-yl)quinoline-3-carbonitrile
• CAS: 1366500-53-9
• 化学式: C₁₈H₁₁N₃
• 分子量: 269.305
• InChiKey: AZWRPRHCWKTPSA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  52.5
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-(1H-indol-3-yl)quinoline-3-carbonitrile 、 3-溴丙炔 在 四丁基溴化铵 、 sodium hydroxide 作用下， 以 水 、 甲苯 为溶剂， 反应 6.0h， 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
• 作为产物：
  描述：

  吲哚 、 2-氯喹啉-3-甲腈 在 三氟乙酸 作用下， 反应 1.0h， 以80%的产率得到2-(1H-indol-3-yl)quinoline-3-carbonitrile
  参考文献：
  名称：

  无金属 TFA 促进的区域选择性（杂）芳基化：（杂）芳基取代和咔唑/奥塞平稠合 N-杂环的合成

  摘要：

  通过氮杂环的氯衍生物的反应在温和条件下实现无金属 TFA 促进的芳基化/杂芳基化[e. g.，=C-C(Cl)=N-] 与富电子芳烃/杂芳烃。还观察到，除了参与杂芳基化步骤外，TFA 还能够在同一锅中促进氢化芳基化/邻芳基化过程，从而提供咔唑/氧杂环庚烯稠合的N-杂环。该反应以克级的相似效率进行。

  DOI：

  10.1002/adsc.202101459

文献信息

• 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
  作者：K. Shiva Kumar、S. Kiran Kumar、B. Yogi Sreenivas、Dhilli Rao Gorja、Ravikumar Kapavarapu、D. Rambabu、G. Rama Krishna、C. Malla Reddy、M.V. Basaveswara Rao、Kishore V.L. Parsa、Manojit Pal

  DOI：10.1016/j.bmc.2012.02.027

  日期：2012.4

  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.
• Metal‐Free TFA‐Promoted Regioselective (Hetero)Arylation: Synthesis of (Hetero)Aryl Substituted and Carbazole/Oxepine Fused <i>N</i> ‐Heterocycles
  作者：Ramanna Jatoth、Praveen Kumar Naikawadi、Boyapally Bhaskar、Kishan Gugulothu、Peramalla Edukondalu、K. Shiva Kumar

  DOI：10.1002/adsc.202101459

  日期：2022.3.30

  Metal-free TFA promoted arylation/heteroarylation was achieved under mild conditions via the reaction of chloro-derivatives of nitrogen heterocycles [e. g., =C−C(Cl)=N−] with electron rich arenes/heteroarenes. It was also observed that apart from participating in the heteroarylation step, TFA was able to facilitate the hydroarylation/o-arylation process in the same pot affording the carbazole/oxepine

  通过氮杂环的氯衍生物的反应在温和条件下实现无金属 TFA 促进的芳基化/杂芳基化[e. g.，=C-C(Cl)=N-] 与富电子芳烃/杂芳烃。还观察到，除了参与杂芳基化步骤外，TFA 还能够在同一锅中促进氢化芳基化/邻芳基化过程，从而提供咔唑/氧杂环庚烯稠合的N-杂环。该反应以克级的相似效率进行。