2-(4-benzylpiperidin-1-yl)-1-(6-methoxy-1H-indol-3-yl)ethanone | 847035-75-0

• 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: 2-(4-benzylpiperidin-1-yl)-1-(6-methoxy-1H-indol-3-yl)ethanone
• CAS: 847035-75-0
• 化学式: C₂₃H₂₆N₂O₂
• 分子量: 362.472
• InChiKey: BVMMGXUPQXGQGU-UHFFFAOYSA-N

物化性质

• 沸点：
  558.7±40.0 °C(Predicted)
• 密度：
  1.172±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.5
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 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：

  2-(4-benzylpiperidin-1-yl)-1-(6-methoxy-1H-indol-3-yl)ethanone 在 三溴化硼 作用下， 以 二氯甲烷 为溶剂， 反应 10.0h， 以68%的产率得到2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Characterization of 3-Substituted-1H-indoles as Ligands of GluN2B-Containing N-Methyl-d-aspartate Receptors

  摘要：

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.

  DOI：

  10.1021/jm2008002
• 作为产物：
  描述：

  6-甲氧基吲哚 在 potassium carbonate 、 三氯氧磷 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 2.67h， 生成 2-(4-benzylpiperidin-1-yl)-1-(6-methoxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis and Biological Characterization of 3-Substituted-1H-indoles as Ligands of GluN2B-Containing N-Methyl-d-aspartate Receptors

  摘要：

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.

  DOI：

  10.1021/jm2008002

文献信息

• Synthesis and Biological Characterization of 3-Substituted-1<i>H</i>-indoles as Ligands of GluN2B-Containing <i>N</i>-Methyl-<scp>d</scp>-aspartate Receptors
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Maria Rosa Buemi、Emilio Russo、Giovambattista De Sarro、Lara Costa、Lucia Ciranna、Orazio Prezzavento、Emanuela Arena、Simone Ronsisvalle、Giuseppe Bruno、Alba Chimirri

  DOI：10.1021/jm2008002

  日期：2011.12.22

  As an extension of our studies, novel indole derivatives were rationally designed and synthesized as ligands targeted to GluN2B/NMDA receptors. The 2-(4-benzylpiperidin-1-yl)-1-(6-hydroxy-1H-indol-3-yl)ethanone (4i) and 1-(4-benzylpiperidin-l-yl)-2-(6-hydroxy-1H-indol-3-yl)ethane-1,2-dione (6i) showed high binding affinity in [H-3]ifenprodil displacement assay. By computational studies, we suggested the hypothetical interactions playing a significant role during the binding process. However, in functional and in vivo studies the most potent compound 4i did not show any activity whereas it displayed relevant affinity toward the sigma(2) receptor.