4-(2'-trifluoromethoxybenzyloxy)benzonitrile

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 4-(2'-trifluoromethoxybenzyloxy)benzonitrile
• 英文别名: 4-{[2-(Trifluoromethoxy)benzyl]oxy}benzonitrile；4-[[2-(trifluoromethoxy)phenyl]methoxy]benzonitrile
• 化学式: C₁₅H₁₀F₃NO₂
• mdl: MFCD25953472
• 分子量: 293.245
• InChiKey: COXDYJGTFWUKLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.13
• 拓扑面积：
  42.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-(2'-trifluoromethoxybenzyloxy)benzonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 16.0h， 生成 [4-[[2-(Trifluoromethoxy)phenyl]methoxy]phenyl]methanamine
  参考文献：
  名称：

  Benzyloxybenzylammonium chlorides: Simple amine salts that display anticonvulsant activity

  摘要：

  Several antiepileptic drugs exert their activities by inhibiting Na+ currents. Recent studies demonstrated that compounds containing a biaryl-linked motif (Ar-X-Ar') modulate Na+ currents. We, and others, have reported that compounds with an embedded benzyloxyphenyl unit (ArOCH2Ar', OCH2 = X) exhibit potent anticonvulsant activities. Here, we show that benzyloxybenzylammonium chlorides (+H3NCH2C6H4OCH2 Ar' Cl-) displayed notable activities in animal seizure models. Electrophysiological studies of 4-(2'-trifluoromethoxybenzyloxy)benzylammonium chloride (9) using embryonic cortical neurons demonstrated that 9 promoted both fast and slow inactivation of Na+ channels. These findings suggest that the potent anticonvulsant activities of the earlier compounds were due, in part, to the benzyloxyphenyl motif and provide support for the use of the biaryl-linked pharmacophore in future drug design efforts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.031
• 作为产物：
  描述：

  2-(三氟甲氧基)苄基溴 、 4-羟基苯甲腈 在 sodium carbonate 作用下， 以 丙酮 为溶剂， 反应 16.0h， 以84%的产率得到4-(2'-trifluoromethoxybenzyloxy)benzonitrile
  参考文献：
  名称：

  Benzyloxybenzylammonium chlorides: Simple amine salts that display anticonvulsant activity

  摘要：

  Several antiepileptic drugs exert their activities by inhibiting Na+ currents. Recent studies demonstrated that compounds containing a biaryl-linked motif (Ar-X-Ar') modulate Na+ currents. We, and others, have reported that compounds with an embedded benzyloxyphenyl unit (ArOCH2Ar', OCH2 = X) exhibit potent anticonvulsant activities. Here, we show that benzyloxybenzylammonium chlorides (+H3NCH2C6H4OCH2 Ar' Cl-) displayed notable activities in animal seizure models. Electrophysiological studies of 4-(2'-trifluoromethoxybenzyloxy)benzylammonium chloride (9) using embryonic cortical neurons demonstrated that 9 promoted both fast and slow inactivation of Na+ channels. These findings suggest that the potent anticonvulsant activities of the earlier compounds were due, in part, to the benzyloxyphenyl motif and provide support for the use of the biaryl-linked pharmacophore in future drug design efforts. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2013.10.031

文献信息

• Benzyloxybenzylammonium chlorides: Simple amine salts that display anticonvulsant activity
  作者：Hyosung Lee、Alexander S. Gold、Xiao-Fang Yang、Rajesh Khanna、Harold Kohn

  DOI：10.1016/j.bmc.2013.10.031

  日期：2013.12

  Several antiepileptic drugs exert their activities by inhibiting Na+ currents. Recent studies demonstrated that compounds containing a biaryl-linked motif (Ar-X-Ar') modulate Na+ currents. We, and others, have reported that compounds with an embedded benzyloxyphenyl unit (ArOCH2Ar', OCH2 = X) exhibit potent anticonvulsant activities. Here, we show that benzyloxybenzylammonium chlorides (+H3NCH2C6H4OCH2 Ar' Cl-) displayed notable activities in animal seizure models. Electrophysiological studies of 4-(2'-trifluoromethoxybenzyloxy)benzylammonium chloride (9) using embryonic cortical neurons demonstrated that 9 promoted both fast and slow inactivation of Na+ channels. These findings suggest that the potent anticonvulsant activities of the earlier compounds were due, in part, to the benzyloxyphenyl motif and provide support for the use of the biaryl-linked pharmacophore in future drug design efforts. (C) 2013 Elsevier Ltd. All rights reserved.