2-(4-(4-fluorobenzyl)piperidin-1-yl)-1-(5-methoxy-1H-indol-3-yl)ethanone | 1549940-48-8

• 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-(4-fluorobenzyl)piperidin-1-yl)-1-(5-methoxy-1H-indol-3-yl)ethanone
• 英文别名: 2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-1-(5-methoxy-1H-indol-3-yl)ethanone
• CAS: 1549940-48-8
• 化学式: C₂₃H₂₅FN₂O₂
• 分子量: 380.462
• InChiKey: ULJCLXJSYUBCDV-UHFFFAOYSA-N

物化性质

• 熔点：
  200-202 °C
• 沸点：
  562.1±45.0 °C(predicted)
• 密度：
  1.213±0.06 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  28
• 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：
  4

反应信息

• 作为反应物：
  描述：

  2-(4-(4-fluorobenzyl)piperidin-1-yl)-1-(5-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30%的产率得到2-(4-(4-fluorobenzyl)piperidin-1-yl)-1-(5-hydroxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors

  摘要：

  A three-step synthetic pathway has been employed to synthesize a small library of 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl)ethanone and 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl) ethane-1,2-dione derivatives that have been screened in [H-3]ifenprodil competition binding assay. Some compounds exhibited significant binding affinity at nanomolar concentration, the most active being ligand 35 (IC50 = 5.5 nM). Docking experiments suggested the main interactions between 35 and GluN2B-containing NMDA receptors. Notably, the compound 35 reduced NMDA-mediated excitatory post-synaptic currents recorded in mouse hippocampal slices indicating antagonistic effects (50 nM). Moreover, the compound 35 has shown antioxidant effects in a preliminary screening, thus suggesting that it might be considered prototype for future drug development of novel 'dual target' neuroprotective agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.040
• 作为产物：
  描述：

  5-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 2.58h， 生成 2-(4-(4-fluorobenzyl)piperidin-1-yl)-1-(5-methoxy-1H-indol-3-yl)ethanone
  参考文献：
  名称：

  Synthesis, modelling and biological characterization of 3-substituted-1H-indoles as ligands of GluN2B-containing N-methyl-d-aspartate receptors

  摘要：

  A three-step synthetic pathway has been employed to synthesize a small library of 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl)ethanone and 2-(4-arylpiperidin-1-yl)-1-(1H-indol-3-yl) ethane-1,2-dione derivatives that have been screened in [H-3]ifenprodil competition binding assay. Some compounds exhibited significant binding affinity at nanomolar concentration, the most active being ligand 35 (IC50 = 5.5 nM). Docking experiments suggested the main interactions between 35 and GluN2B-containing NMDA receptors. Notably, the compound 35 reduced NMDA-mediated excitatory post-synaptic currents recorded in mouse hippocampal slices indicating antagonistic effects (50 nM). Moreover, the compound 35 has shown antioxidant effects in a preliminary screening, thus suggesting that it might be considered prototype for future drug development of novel 'dual target' neuroprotective agents. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.12.040