(Z)-1-benzyl-4-(4-fluorophenyl)piperidin-3-one O-4-trifluoromethylbenzyl oxime | 1280635-08-6

• 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: (Z)-1-benzyl-4-(4-fluorophenyl)piperidin-3-one O-4-trifluoromethylbenzyl oxime
• 英文别名: (Z)-1-benzyl-4-(4-fluorophenyl)-N-[[4-(trifluoromethyl)phenyl]methoxy]piperidin-3-imine
• CAS: 1280635-08-6
• 化学式: C₂₆H₂₄F₄N₂O
• 分子量: 456.483
• InChiKey: GUEBWXBYBPVFDT-QCKNELIISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.4
• 重原子数：
  33
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.27
• 拓扑面积：
  24.8
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (Z)-1-benzyl-4-(4-fluorophenyl)piperidin-3-one O-4-trifluoromethylbenzyl oxime 在 盐酸 、 10% palladium on activated charcoal 、 氢气 作用下， 以 乙醇 为溶剂， 20.0 ℃ 、101.33 kPa 条件下， 反应 30.0h， 生成 (E)-4-(4-fluorophenyl)piperidin-3-one O-4-(trifluoromethyl)benzyl oxime hydrochloride 、 (Z)-4-(4-fluorophenyl)piperidin-3-one O-4-(trifluoromethyl)benzyl oxime hydrochloride
  参考文献：
  名称：

  Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors

  摘要：

  With the aim of obtaining compounds possessing high SERT selectivity, in the present work we synthesized and studied the inhibition of serotonin (SERT), dopamine (DAT) and norepinephrine (NET) transporters by docking studies and experimental binding measurements of a series of 4-(aryl)piperidin-3-one O-4-benzyl oxime hydrochlorides (1-10) of both E and Z configuration. E configuration compounds showed high SERT binding affinities (K-i = 10-98 nM) and high SERT selectivities over both NET and DAT. The molecular docking studies allowed a rationalization of the molecular basis of drug-SERT interactions both of the synthesized compounds and paroxetine and fluoxetine used as reference antidepressant drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.018
• 作为产物：
  描述：

  1-benzyl-4-(4-fluorophenyl)piperidin-3-one oxime 、 4-(三氟甲基)苄基氯 在 sodium hydride 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 为溶剂， 反应 121.0h， 以85%的产率得到(Z)-1-benzyl-4-(4-fluorophenyl)piperidin-3-one O-4-trifluoromethylbenzyl oxime
  参考文献：
  名称：

  Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors

  摘要：

  With the aim of obtaining compounds possessing high SERT selectivity, in the present work we synthesized and studied the inhibition of serotonin (SERT), dopamine (DAT) and norepinephrine (NET) transporters by docking studies and experimental binding measurements of a series of 4-(aryl)piperidin-3-one O-4-benzyl oxime hydrochlorides (1-10) of both E and Z configuration. E configuration compounds showed high SERT binding affinities (K-i = 10-98 nM) and high SERT selectivities over both NET and DAT. The molecular docking studies allowed a rationalization of the molecular basis of drug-SERT interactions both of the synthesized compounds and paroxetine and fluoxetine used as reference antidepressant drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2010.12.018

文献信息

• Synthesis, molecular docking and binding studies of selective serotonin transporter inhibitors
  作者：Susanna Nencetti、Maria R. Mazzoni、Gabriella Ortore、Annalina Lapucci、Janette Giuntini、Elisabetta Orlandini、Irene Banti、Elisa Nuti、Antonio Lucacchini、Gino Giannaccini、Armando Rossello

  DOI：10.1016/j.ejmech.2010.12.018

  日期：2011.3

  With the aim of obtaining compounds possessing high SERT selectivity, in the present work we synthesized and studied the inhibition of serotonin (SERT), dopamine (DAT) and norepinephrine (NET) transporters by docking studies and experimental binding measurements of a series of 4-(aryl)piperidin-3-one O-4-benzyl oxime hydrochlorides (1-10) of both E and Z configuration. E configuration compounds showed high SERT binding affinities (K-i = 10-98 nM) and high SERT selectivities over both NET and DAT. The molecular docking studies allowed a rationalization of the molecular basis of drug-SERT interactions both of the synthesized compounds and paroxetine and fluoxetine used as reference antidepressant drugs. (C) 2010 Elsevier Masson SAS. All rights reserved.