3-(4-aminophenoxy)-N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methylpropanamine | 143665-62-7

• 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: 3-(4-aminophenoxy)-N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methylpropanamine
• 英文别名: N-<3-(4-aminophenoxy)propyl>-3,4-dimethoxy-N-methylbenzeneethanamine；N-[3-(4-Aminophenoxy)propyl]-3,4-dimethoxy-N-methylbenzeneethanamine；4-[3-[2-(3,4-Dimethoxyphenyl)ethyl-methylamino]propoxy]aniline
• CAS: 143665-62-7
• 化学式: C₂₀H₂₈N₂O₃
• 分子量: 344.454
• InChiKey: VBAIORXXMFEWFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  25
• 可旋转键数：
  10
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  57
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-羧基-9-茚酮 、 3-(4-aminophenoxy)-N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methylpropanamine 在 1-羟基苯并三唑一水物 、 N,N'-二环己基碳二亚胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 N-[4-[3-[[2-(3,4-dimethoxyphenyl)ethyl]methylamino]propoxy]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：

  1-(3-溴丙氧基)-4-硝基苯 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 25.0~140.0 ℃ 、101.33 kPa 条件下， 反应 0.5h， 生成 3-(4-aminophenoxy)-N-<2-(3,4-dimethoxyphenyl)ethyl>-N-methylpropanamine
  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

• Novel-N-(4-(Aminosubstituted)phenyl) methanesulfonamides and their use as cardiovascular agents
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0332570A2

  公开（公告）日：1989-09-13

  Novel N-[4-aminosubstituted)phenyl]methane­sulfonamides and their use as cardiovascular agents, especially as antiarrhythmic agents are described. Pharmaceutical formulations containing such compounds are also discussed.

  介绍了新型 N-[4-氨基取代)苯基]甲磺酰胺类化合物及其作为心血管药物，特别是作为抗心律失常药物的用途。还讨论了含有此类化合物的药物制剂。
• Synthesis, electrophysiological properties and analysis of structural requirements of a novel class of antiarrhythmic agents with potassium and calcium channel blocking properties
  作者：Guy Nadler、Jean-François Faivre、Marie-Claire Forest、Brigitte Cheval、Michel Martin、Michel Souchet、Bernard Gout、Antoine Bril

  DOI：10.1016/s0968-0896(98)00166-7

  日期：1998.11

  Class III antiarrhythmic agents have been shown to prevent reentrant arrhythmias but also to be responsible for initiating arrhythmias characterised by afterdepolarizations and triggered activities. By combining potassium and calcium channel antagonistic actions, as with BRL-32872(1,2) (1), it might be possible to reduce the incidence of proarrhythmias albeit retaining antiarrhythmic efficacy. In the present study we synthesised and tested for their electrophysiological activity in guinea pig papillary muscle a wide panel of analogues of BRL-32872. Some qualitative relationships between compound structure and the inhibitory effect on the rapidly activating component of the delayed rectifier potassium current and/or the L-type calcium current will be presented. New derivatives depicting bell-shaped dose-response curves on action potential duration may therefore represent novel agents for improved antiarrhythmic therapy. (C) 1998 Elsevier Science Ltd. All rights reserved.
• 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
• ANILIDE DERIVATIVES
  申请人：LABORATOIRES GLAXO SA

  公开号：EP0649410A1

  公开（公告）日：1995-04-26