N-[(3,4-dimethoxyphenyl)methyl]-N-methyl-4-(4-nitrophenyl)butanamide | 143665-55-8

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: N-[(3,4-dimethoxyphenyl)methyl]-N-methyl-4-(4-nitrophenyl)butanamide
• CAS: 143665-55-8
• 化学式: C₂₀H₂₄N₂O₅
• 分子量: 372.421
• InChiKey: YKZPJZIWDVMZOX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  27
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  84.6
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  N-[(3,4-dimethoxyphenyl)methyl]-N-methyl-4-(4-nitrophenyl)butanamide 在 palladium on activated charcoal lithium aluminium tetrahydride 、 氢气 、 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 乙醇 、 N,N-二甲基甲酰胺 为溶剂， 25.0 ℃ 、101.33 kPa 条件下， 反应 3.0h， 生成 N-[4-[4-[[(3,4-dimethoxyphenyl)methyl]methylamino]butyl]phenyl]-9,10-dihydro-9-oxo-4-acridinecarboxamide
  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-(4-硝基苯)丁酸 在 氯化亚砜 、 碳酸氢钠 作用下， 以 丙酮 为溶剂， 反应 9.0h， 生成 N-[(3,4-dimethoxyphenyl)methyl]-N-methyl-4-(4-nitrophenyl)butanamide
  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：EP0569380B1

  公开（公告）日：1997-05-28
• US5604237A
  申请人：——

  公开号：US5604237A

  公开（公告）日：1997-02-18
• Synthesis and Activity against Multidrug Resistance in Chinese Hamster Ovary Cells of New Acridone-4-carboxamides
  作者：Nerina Dodic、Bernard Dumaitre、Alain Daugan、Pascal Pianetti

  DOI：10.1021/jm00013a017

  日期：1995.6

  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.