6-(1H-indol-5-yl)nicotinaldehyde

• 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: 6-(1H-indol-5-yl)nicotinaldehyde
• 英文别名: 6-(1H-indol-5-yl)pyridine-3-carbaldehyde
• 化学式: C₁₄H₁₀N₂O
• 分子量: 222.246
• InChiKey: LQJGDOAFPAJVCT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  45.8
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  5-溴吲哚 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 1,1'-双(二苯膦基)二茂铁二氯化钯(II)二氯甲烷复合物 、 potassium acetate 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 水 为溶剂， 反应 13.33h， 生成 6-(1H-indol-5-yl)nicotinaldehyde
  参考文献：
  名称：

  Design, synthesis and biological evaluation of indole derivatives as Vif inhibitors

  摘要：

  The crystal structure of viral infectivity factor (Vif) was reported recently, which makes it possible to design new inhibitors against Vif by structure-based drug design. Through analysis of the protein surface of Vif, the C2 pocket located in the N-terminal was found, which is suit for developing small molecular inhibitors. Then, in our article, fragment-based virtual screening (FBVS) was conducted and a series of fragments was obtained, among which, Zif-1 bearing indole scaffold and pyridine ring can form H-bonds with Tyr148 and Ilel 55. Subsequently, 19 derivatives of Zif-1 were synthesized. Through the immune fluorescence staining and Western blot assays, Zif-15 shows potent activity in inhibiting Vif-mediated A3G degradation. Further docking experiment shows that Zif-15 form H-bond interactions with residues His139, Tyr148 and Ilel 55. Therefore, Zif-15 is a promising lead compound against Vif that can be used to treat AIDS. (C) 2017 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2017.07.026

文献信息

• Design, synthesis and biological evaluation of indole derivatives as Vif inhibitors
  作者：Chunlan Pu、Rong-Hua Luo、Mengqi Zhang、Xueyan Hou、Guoyi Yan、Jiang Luo、Yong-Tang Zheng、Rui Li

  DOI：10.1016/j.bmcl.2017.07.026

  日期：2017.9

  The crystal structure of viral infectivity factor (Vif) was reported recently, which makes it possible to design new inhibitors against Vif by structure-based drug design. Through analysis of the protein surface of Vif, the C2 pocket located in the N-terminal was found, which is suit for developing small molecular inhibitors. Then, in our article, fragment-based virtual screening (FBVS) was conducted and a series of fragments was obtained, among which, Zif-1 bearing indole scaffold and pyridine ring can form H-bonds with Tyr148 and Ilel 55. Subsequently, 19 derivatives of Zif-1 were synthesized. Through the immune fluorescence staining and Western blot assays, Zif-15 shows potent activity in inhibiting Vif-mediated A3G degradation. Further docking experiment shows that Zif-15 form H-bond interactions with residues His139, Tyr148 and Ilel 55. Therefore, Zif-15 is a promising lead compound against Vif that can be used to treat AIDS. (C) 2017 Published by Elsevier Ltd.