2-(4-aminophenoxy)-N-benzyl-N-methylacetamide | 143666-84-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: 2-(4-aminophenoxy)-N-benzyl-N-methylacetamide
• CAS: 143666-84-6
• 化学式: C₁₆H₁₈N₂O₂
• 分子量: 270.331
• InChiKey: JCVPLFJCFDWTCF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  20
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-(4-aminophenoxy)-N-benzyl-N-methylacetamide 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 4-[2-[Benzyl(methyl)amino]ethoxy]aniline
  参考文献：
  名称：

  Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides

  摘要：

  A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the (CHC)-C-R/5 cell line. Among them the acridone derivatives were the most potent, A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain. Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone. On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy- 9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)ethyl]phenyl]-4-acridinecarboxamide (84) has been selected for further development.

  DOI：

  10.1021/jm00013a017
• 作为产物：
  描述：

  4-硝基苯氧乙酸 在 palladium on activated charcoal 氯化亚砜 、 氢气 、 碳酸氢钠 作用下， 以 乙醇 、 丙酮 为溶剂， 25.0~60.0 ℃ 、101.33 kPa 条件下， 反应 8.0h， 生成 2-(4-aminophenoxy)-N-benzyl-N-methylacetamide
  参考文献：
  名称：

  Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides

  摘要：

  A number of tricyclic carboxamides have been synthesized and tested to evaluate their ability to reverse multidrug resistance in the (CHC)-C-R/5 cell line. Among them the acridone derivatives were the most potent, A key feature is the presence of a dimethoxybenzyl or phenethylamine cationic site, separated from the tricyclic lipophilic part by a carbamoylphenyl chain. Optimization led to compounds 2 orders of magnitude more active than the prototype inhibitors verapamil and amiodarone. On the basis of in vitro and in vivo activities, 9,10-dihydro-5-methoxy- 9-oxo-N-[4-[2-(1,2,3,4-tetrahydro-6,7-dimethoxyisoquinol-2-yl)ethyl]phenyl]-4-acridinecarboxamide (84) has been selected for further development.

  DOI：

  10.1021/jm00013a017

文献信息

• EP0494623A1
  申请人：——

  公开号：EP0494623A1

  公开（公告）日：1992-07-15
• ACRIDINE DERIVATIVES
  申请人：LABORATOIRES GLAXO SA

  公开号：EP0569380A1

  公开（公告）日：1993-11-18
• ANILIDE DERIVATIVES
  申请人：LABORATOIRES GLAXO SA

  公开号：EP0649410A1

  公开（公告）日：1995-04-26
• US5604237A
  申请人：——

  公开号：US5604237A

  公开（公告）日：1997-02-18
• US5663179A
  申请人：——

  公开号：US5663179A

  公开（公告）日：1997-09-02