4-(2-{[2-(4-Amino-phenyl)-ethyl]-methyl-amino}-ethoxy)-N-methyl-benzamide | 115256-27-4

• 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: 4-(2-{[2-(4-Amino-phenyl)-ethyl]-methyl-amino}-ethoxy)-N-methyl-benzamide
• 英文别名: 4-[2-[2-(4-aminophenyl)ethyl-methylamino]ethoxy]-N-methylbenzamide
• CAS: 115256-27-4
• 化学式: C₁₉H₂₅N₃O₂
• 分子量: 327.426
• InChiKey: CYAAAIXVUJKEGV-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  24
• 可旋转键数：
  8
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  67.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-(2-{[2-(4-Amino-phenyl)-ethyl]-methyl-amino}-ethoxy)-N-methyl-benzamide 、 甲基磺酸酐 以 二氯甲烷 为溶剂， 以19%的产率得到4-(2-{[2-(4-Methanesulfonylamino-phenyl)-ethyl]-methyl-amino}-ethoxy)-N-methyl-benzamide
  参考文献：
  名称：

  Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines

  摘要：

  A series of bis(arylalkyl)amines is described and their effects on prolonging effective refractory period in isolated cardiac tissue listed. Most compounds prolonged the cardiac action potential without significantly altering the maximum rate of depolarization and may be defined as selective class III antiarrhythmic agents. It was found that a particularly advantageous structural feature was to have a methanesulfonamido moiety on both of the aryl rings. Thus, compound 16 [1-(4-methanesulfonamidophenoxy)2-[N-(4-methanesulfonamidophene thyl)-N- methylamine]ethane] was selected for further investigations. The compound is highly potent and selective class III agent which acts by blockade of cardiac potassium channels.

  DOI：

  10.1021/jm00166a011
• 作为产物：
  描述：

  N-甲基-[2-(4-硝基-苯基)-乙基]-胺 在 氢气 、 potassium carbonate 、 sodium iodide 作用下， 以 乙醇 、 乙腈 为溶剂， 反应 72.0h， 生成 4-(2-{[2-(4-Amino-phenyl)-ethyl]-methyl-amino}-ethoxy)-N-methyl-benzamide
  参考文献：
  名称：

  Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines

  摘要：

  A series of bis(arylalkyl)amines is described and their effects on prolonging effective refractory period in isolated cardiac tissue listed. Most compounds prolonged the cardiac action potential without significantly altering the maximum rate of depolarization and may be defined as selective class III antiarrhythmic agents. It was found that a particularly advantageous structural feature was to have a methanesulfonamido moiety on both of the aryl rings. Thus, compound 16 [1-(4-methanesulfonamidophenoxy)2-[N-(4-methanesulfonamidophene thyl)-N- methylamine]ethane] was selected for further investigations. The compound is highly potent and selective class III agent which acts by blockade of cardiac potassium channels.

  DOI：

  10.1021/jm00166a011

文献信息

• N-substituted p-aminoethylsulphon anilides as antiarrhythmic agents, and intermediates therefor
  申请人：Pfizer Limited

  公开号：EP0245997B1

  公开（公告）日：1992-04-15
• CROSS, PETER E.;ARROWSMITH, JOHN E.;THOMAS, GEOFFREY N.;GWILT, MICHAEL;BU+, J. MED. CHEM., 33,(1990) N, C. 1151-1155
  作者：CROSS, PETER E.、ARROWSMITH, JOHN E.、THOMAS, GEOFFREY N.、GWILT, MICHAEL、BU+

  DOI：——

  日期：——
• US4959366A
  申请人：——

  公开号：US4959366A

  公开（公告）日：1990-09-25
• US5079248A
  申请人：——

  公开号：US5079248A

  公开（公告）日：1992-01-07
• Selective class III antiarrhythmic agents. 1. Bis(arylalkyl)amines
  作者：Peter E. Cross、John E. Arrowsmith、Geoffrey N. Thomas、Michael Gwilt、Roger A. Burges、Alan J. Higgins

  DOI：10.1021/jm00166a011

  日期：1990.4

  A series of bis(arylalkyl)amines is described and their effects on prolonging effective refractory period in isolated cardiac tissue listed. Most compounds prolonged the cardiac action potential without significantly altering the maximum rate of depolarization and may be defined as selective class III antiarrhythmic agents. It was found that a particularly advantageous structural feature was to have a methanesulfonamido moiety on both of the aryl rings. Thus, compound 16 [1-(4-methanesulfonamidophenoxy)2-[N-(4-methanesulfonamidophene thyl)-N- methylamine]ethane] was selected for further investigations. The compound is highly potent and selective class III agent which acts by blockade of cardiac potassium channels.