tert-butyl 3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)-2-oxoacetyl)-1H-indol-6-ylcarbamate | 1549940-74-0

• 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: tert-butyl 3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)-2-oxoacetyl)-1H-indol-6-ylcarbamate
• 英文别名: tert-butyl N-[3-[2-[4-[(4-fluorophenyl)methyl]piperidin-1-yl]-2-oxoacetyl]-1H-indol-6-yl]carbamate
• CAS: 1549940-74-0
• 化学式: C₂₇H₃₀FN₃O₄
• 分子量: 479.551
• InChiKey: FDLWUKNMHLMLEZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.8
• 重原子数：
  35
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  91.5
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  tert-butyl 3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)-2-oxoacetyl)-1H-indol-6-ylcarbamate 在 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以65%的产率得到1-(6-amino-1H-indol-3-yl)-2-(4-(4-fluorobenzyl)piperidin-1-yl)ethane-1,2-dione
  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：

  (1H-吲哚-6-基)-氨基甲酸叔丁酯 在 O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate 作用下， 以 乙醚 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.5h， 生成 tert-butyl 3-(2-(4-(4-fluorobenzyl)piperidin-1-yl)-2-oxoacetyl)-1H-indol-6-ylcarbamate
  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