2-(3-benzoylphenyl)-N-(1H-indol-6-yl)-N-propylpropanamide | 1239447-58-5

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-(3-benzoylphenyl)-N-(1H-indol-6-yl)-N-propylpropanamide
• CAS: 1239447-58-5
• 化学式: C₂₇H₂₆N₂O₂
• 分子量: 410.516
• InChiKey: VTUGOOXWWOIQNC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.8
• 重原子数：
  31
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  53.2
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  N-propyl-1H-indol-6-amine 、 右旋酮洛芬 在 N,N-二异丙基乙胺 、 Methanaminium,N-[(dimethylamino)(3H-1,2,3-triazolo[4,5-b]pyridin-3-yloxy)methylene]-N-methyl-, hexafluorophosphate(1-) 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.5h， 以73%的产率得到2-(3-benzoylphenyl)-N-(1H-indol-6-yl)-N-propylpropanamide
  参考文献：
  名称：

  Amide conjugates of ketoprofen and indole as inhibitors of Gli1-mediated transcription in the Hedgehog pathway

  摘要：

  We have previously reported small-molecule inhibitors of Gli1-mediated transcription, an essential down-stream element of the Hh pathway. We created new derivatives of the previous compounds aiming to improve the druggable properties. The new compounds, amide conjugates of ketoprofen and indole, showed inhibitory activity and membrane permeability, while also improving the microsome stability. Among them, 33 and 42 inhibited Gli-luciferase reporter in C3H10T1/2 cells that were exogenously transfected with Gli1 with 2.6 mu M and 1.6 mu M of IC50, respectively, and in Rh30 cells that endogenously over-express Gli1, and were selective to Gli1 over Gli2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2010.05.001

文献信息

• Amide conjugates of ketoprofen and indole as inhibitors of Gli1-mediated transcription in the Hedgehog pathway
  作者：Neeraj Mahindroo、Michele C. Connelly、Chandanamali Punchihewa、Lei Yang、Bing Yan、Naoaki Fujii

  DOI：10.1016/j.bmc.2010.05.001

  日期：2010.7

  We have previously reported small-molecule inhibitors of Gli1-mediated transcription, an essential down-stream element of the Hh pathway. We created new derivatives of the previous compounds aiming to improve the druggable properties. The new compounds, amide conjugates of ketoprofen and indole, showed inhibitory activity and membrane permeability, while also improving the microsome stability. Among them, 33 and 42 inhibited Gli-luciferase reporter in C3H10T1/2 cells that were exogenously transfected with Gli1 with 2.6 mu M and 1.6 mu M of IC50, respectively, and in Rh30 cells that endogenously over-express Gli1, and were selective to Gli1 over Gli2. (C) 2010 Elsevier Ltd. All rights reserved.