2-(4-benzylpiperazin-1-yl)-1-(1H-indol-3-yl)ethanone | 324059-16-7

• 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: 2-(4-benzylpiperazin-1-yl)-1-(1H-indol-3-yl)ethanone
• CAS: 324059-16-7
• 化学式: C₂₁H₂₃N₃O
• mdl: MFCD00377748
• 分子量: 333.433
• InChiKey: GFPMJRSSACBKGL-UHFFFAOYSA-N

物化性质

• 沸点：
  536.0±45.0 °C(Predicted)
• 密度：
  1.206±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.285
• 拓扑面积：
  39.3
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  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 2-(4-benzylpiperazin-1-yl)-1-(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

• Development of 3-substituted-1H-indole derivatives as NR2B/NMDA receptor antagonists
  作者：Rosaria Gitto、Laura De Luca、Stefania Ferro、Rita Citraro、Giovambattista De Sarro、Lara Costa、Lucia Ciranna、Alba Chimirri

  DOI：10.1016/j.bmc.2008.12.058

  日期：2009.2

  previously allowed us to identify NR2B/NMDA receptor antagonists containing indole scaffold. In order to further explore the main structure activity relationships of this class of derivatives we herein report the design, synthesis and biological evaluation of new analogues. Some derivatives demonstrated to produce significant anticonvulsant properties and NMDA antagonism. The most active of them (3d)

  以前基于配体和基于结构的组合方法使我们能够鉴定出含有吲哚支架的NR2B / NMDA受体拮抗剂。为了进一步探索这类衍生物的主要结构活性关系，我们在此报告了新类似物的设计，合成和生物学评估。一些衍生物被证明具有显着的抗惊厥特性和NMDA拮抗作用。其中最活跃的（3d）与ifenprodil的NR2B结合亲和力相等。这些结果也得到了计算研究的证实。
• 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.