1-(5-methoxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl)ethanone | 1531588-05-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1-(5-methoxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl)ethanone
• CAS: 1531588-05-2
• 化学式: C₂₂H₂₄N₂O₂
• 分子量: 348.445
• InChiKey: VPVQIWNLYOXDFQ-UHFFFAOYSA-N

物化性质

• 熔点：
  219 °C (decomp)
• 沸点：
  555.1±50.0 °C(predicted)
• 密度：
  1.180±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  45.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  1-(5-methoxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl)ethanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以10%的产率得到1-(5-hydroxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl)ethanone
  参考文献：
  名称：

  From NMDA receptor antagonists to discovery of selective σ2 receptor ligands

  摘要：

  Following previous studies focused on the search for new molecules targeting GluN2B-containing NMDA, a small series of 1-(1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl) ethanone derivatives has been synthesized by using Microwave Assisted Organic Synthesis (MAOS). Given that GluN2B ligands frequently exert off-target effects we also tested their affinity towards sigma receptors. Binding assay revealed that only the 1-(5-hydroxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl) ethanone (7a) retained GluN2B affinity. Interestingly, the 5-methoxyindoles 5a and 6a were efficient and selective ligands toward sigma 2 receptor (K-i values of 10 nM and 20 nM, respectively). Thus, in this case the discovery of new sigma 2 receptor selective ligands was an unexpected result emerging from the screening of cross-activity against other CNS receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.014
• 作为产物：
  描述：

  5-甲氧基吲哚 在 吡啶 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 N,N-二甲基甲酰胺 为溶剂， 反应 0.25h， 生成 1-(5-methoxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl)ethanone
  参考文献：
  名称：

  From NMDA receptor antagonists to discovery of selective σ2 receptor ligands

  摘要：

  Following previous studies focused on the search for new molecules targeting GluN2B-containing NMDA, a small series of 1-(1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl) ethanone derivatives has been synthesized by using Microwave Assisted Organic Synthesis (MAOS). Given that GluN2B ligands frequently exert off-target effects we also tested their affinity towards sigma receptors. Binding assay revealed that only the 1-(5-hydroxy-1H-indol-3-yl)-2-(4-phenylpiperidin-1-yl) ethanone (7a) retained GluN2B affinity. Interestingly, the 5-methoxyindoles 5a and 6a were efficient and selective ligands toward sigma 2 receptor (K-i values of 10 nM and 20 nM, respectively). Thus, in this case the discovery of new sigma 2 receptor selective ligands was an unexpected result emerging from the screening of cross-activity against other CNS receptors. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.11.014