1-(5-hydroxy-1H-indol-3-yl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)ethanone | 1531588-12-1

• 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-hydroxy-1H-indol-3-yl)-2-(4-hydroxy-4-phenylpiperidin-1-yl)ethanone
• CAS: 1531588-12-1
• 化学式: C₂₁H₂₂N₂O₃
• 分子量: 350.417
• InChiKey: INEIQXCEYQJKLK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  76.6
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  5-甲氧基吲哚 在 吡啶 、 三溴化硼 、 potassium carbonate 作用下， 以 1,4-二氧六环 、 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 10.25h， 生成 1-(5-hydroxy-1H-indol-3-yl)-2-(4-hydroxy-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

文献信息

• From NMDA receptor antagonists to discovery of selective σ2 receptor ligands
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Angela Scala、Simone Ronsisvalle、Carmela Parenti、Orazio Prezzavento、Maria Rosa Buemi、Alba Chimirri

  DOI：10.1016/j.bmc.2013.11.014

  日期：2014.1

  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.