N-<4-<<2-(diethylamino)ethyl>amino>phenyl>methanesulfonamide | 123507-59-5

• 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-<4-<<2-(diethylamino)ethyl>amino>phenyl>methanesulfonamide
• 英文别名: N-[4-[[2-(Diethylamino)ethyl]amino]phenyl]methanesulfonamide；N-[4-[2-(diethylamino)ethylamino]phenyl]methanesulfonamide
• CAS: 123507-59-5
• 化学式: C₁₃H₂₃N₃O₂S
• 分子量: 285.411
• InChiKey: LDUYQBDLIDWETE-UHFFFAOYSA-N

物化性质

• 沸点：
  432.9±55.0 °C(Predicted)
• 密度：
  1.193±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  19
• 可旋转键数：
  8
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.54
• 拓扑面积：
  69.8
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-<(methylsulfonyl)amino>benzoyl chloride 、 N-<4-<<2-(diethylamino)ethyl>amino>phenyl>methanesulfonamide 以 四氢呋喃 为溶剂， 反应 17.0h， 以35%的产率得到N-<2-(diethylamino)ethyl>-4-<(methylsufonyl)amino>-N-<4-<(methylsulfonyl)amino>phenyl>benzamide
  参考文献：
  名称：

  Synthesis and cardiac electrophysiological activity of aryl-substituted derivatives of the class III antiarrhythmic agent sematilide. Potential class I/III agents

  摘要：

  Twelve novel derivatives of the selective class III antiarrhythmic agent sematilide were prepared in an attempt to incorporate both class I and class III electrophysiological properties into a single molecule. Electrophysiological activity was determined by standard microelectrode techniques in canine cardiac Purkinje fibers. Initial assessment of class I efficacy was carried out in a ouabain-induced arrhythmia model in guinea pigs. All of the compounds prolonged action potential duration in Purkinje fibers (class III activity), and three were active against ouabain-induced arrhythmias (class I activity). Selected compounds were evaluated further in dogs for efficacy against arrhythmias occurring 24 h following coronary ligation (automatic arrhythmias) and induced by using programmed electrical stimulation techniques (reentrant arrhythmias). The most effective compounds from the series are 3g and -j, which were effective in both canine models. Molecular modeling and structure-activity relationships are discussed.

  DOI：

  10.1021/jm00164a025
• 作为产物：
  描述：

  2-二乙氨基氯乙烷盐酸盐 、 4-甲磺酰胺基苯胺 以 甲苯 为溶剂， 反应 18.0h， 以62%的产率得到N-<4-<<2-(diethylamino)ethyl>amino>phenyl>methanesulfonamide
  参考文献：
  名称：

  Synthesis and cardiac electrophysiological activity of aryl-substituted derivatives of the class III antiarrhythmic agent sematilide. Potential class I/III agents

  摘要：

  Twelve novel derivatives of the selective class III antiarrhythmic agent sematilide were prepared in an attempt to incorporate both class I and class III electrophysiological properties into a single molecule. Electrophysiological activity was determined by standard microelectrode techniques in canine cardiac Purkinje fibers. Initial assessment of class I efficacy was carried out in a ouabain-induced arrhythmia model in guinea pigs. All of the compounds prolonged action potential duration in Purkinje fibers (class III activity), and three were active against ouabain-induced arrhythmias (class I activity). Selected compounds were evaluated further in dogs for efficacy against arrhythmias occurring 24 h following coronary ligation (automatic arrhythmias) and induced by using programmed electrical stimulation techniques (reentrant arrhythmias). The most effective compounds from the series are 3g and -j, which were effective in both canine models. Molecular modeling and structure-activity relationships are discussed.

  DOI：

  10.1021/jm00164a025

文献信息

• Novel N-[4-(aminosubstituted)phenyl]methanesulfonamides and their use as
  申请人：Schering A.G.

  公开号：US04906634A1

  公开（公告）日：1990-03-06

  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.

  本文描述了新型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，特别是抗心律失常药物的用途。还讨论了含有这些化合物的制药配方。
• 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。
• GREENBERG, STANLEY S.;LUMMA, WILLIAM C. (JR);NICKISCH, KLAUS;WOHL, RONALD+
  作者：GREENBERG, STANLEY S.、LUMMA, WILLIAM C. (JR)、NICKISCH, KLAUS、WOHL, RONALD+

  DOI：——

  日期：——
• US4906634A
  申请人：——

  公开号：US4906634A

  公开（公告）日：1990-03-06
• Synthesis and cardiac electrophysiological activity of aryl-substituted derivatives of the class III antiarrhythmic agent sematilide. Potential class I/III agents
  作者：Gary B. Phillips、Thomas K. Morgan、Klaus Nickisch、Joan M. Lind、Robert P. Gomez、Ronald A. Wohl、Thomas M. Argentieri、Mark E. Sullivan

  DOI：10.1021/jm00164a025

  日期：1990.2

  Twelve novel derivatives of the selective class III antiarrhythmic agent sematilide were prepared in an attempt to incorporate both class I and class III electrophysiological properties into a single molecule. Electrophysiological activity was determined by standard microelectrode techniques in canine cardiac Purkinje fibers. Initial assessment of class I efficacy was carried out in a ouabain-induced arrhythmia model in guinea pigs. All of the compounds prolonged action potential duration in Purkinje fibers (class III activity), and three were active against ouabain-induced arrhythmias (class I activity). Selected compounds were evaluated further in dogs for efficacy against arrhythmias occurring 24 h following coronary ligation (automatic arrhythmias) and induced by using programmed electrical stimulation techniques (reentrant arrhythmias). The most effective compounds from the series are 3g and -j, which were effective in both canine models. Molecular modeling and structure-activity relationships are discussed.