N-<2-(diethylamino)-2-(1-naphthalenyl)ethyl>-4-<(methylsulfonyl)amino>benzamide | 116855-42-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: N-<2-(diethylamino)-2-(1-naphthalenyl)ethyl>-4-<(methylsulfonyl)amino>benzamide
• 英文别名: N-[2-(Diethylamino)-2-(naphthalen-1-yl)ethyl]-4-[(methylsulfonyl)amino]benzamide；N-[2-(diethylamino)-2-naphthalen-1-ylethyl]-4-(methanesulfonamido)benzamide
• CAS: 116855-42-6
• 化学式: C₂₄H₂₉N₃O₃S
• 分子量: 439.579
• InChiKey: IKQSFTKYZOOYEX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  31
• 可旋转键数：
  9
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  86.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  α-(diethylamino)-1-naphthaleneacetonitrile 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 33.0h， 生成 N-<2-(diethylamino)-2-(1-naphthalenyl)ethyl>-4-<(methylsulfonyl)amino>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

文献信息

• ARYL-N-AMINOALKYL-4-(SULFONAMIDO)BENZAMIDES, ANTIARRHYTMIC AGENTS AND COMPOSITIONS THEREOF
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：EP0324791A1

  公开（公告）日：1989-07-26
• US4920116A
  申请人：——

  公开号：US4920116A

  公开（公告）日：1990-04-24
• [EN] ARYL-N-AMINOALKYL-4-(SULFONAMIDO)BENZAMIDES, ANTIARRHYTMIC AGENTS AND COMPOSITIONS THEREOF
  申请人：SCHERING AKTIENGESELLSCHAFT

  公开号：WO1988002362A1

  公开（公告）日：1988-04-07

  (EN) Novel aryl-N-aminoalkyl-4-(sulfonamido)benzamides are described as useful antiarrhytmic agents. Their use in the treatment of cardiac arrhytmias especially as combination class I/class III agents is described. Pharmaceutical formulations containing such compounds are also disclosed.(FR) Les aryl-N-aminoalkyl-4-(sulfonamido)benzamides décrites sont utiles en tant qu'agents antiarythmiques. Leur utilisation dans le traitement d'arrythmie cardiaque, spécialement comme agents de la combinaison de la classe I et de la classe III est décrite. Des compositions pharmaceutiques contenant de tels composés sont également décrites.
• 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.