N-[4-[4-(ethylamino)butyl]phenyl]methanesulfonamide | 178622-28-1

• 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-[4-(ethylamino)butyl]phenyl]methanesulfonamide
• CAS: 178622-28-1
• 化学式: C₁₃H₂₂N₂O₂S
• 分子量: 270.396
• InChiKey: CROAKIWNCSDLHJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 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：
  66.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-溴-7-氟庚烷 、 N-[4-[4-(ethylamino)butyl]phenyl]methanesulfonamide 在 碳酸氢钠 作用下， 以 乙腈 为溶剂， 反应 16.0h， 以47.4%的产率得到N-[4-[4-[ethyl(7-fluoroheptyl)amino]butyl]phenyl]methanesulfonamide
  参考文献：
  名称：

  Progress toward the Development of a Safe and Effective Agent for Treating Reentrant Cardiac Arrhythmias:  Synthesis and Evaluation of Ibutilide Analogues with Enhanced Metabolic Stability and Diminished Proarrhythmic Potential

  摘要：

  A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.

  DOI：

  10.1021/jm0004289
• 作为产物：
  描述：

  在 lithium aluminium tetrahydride 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 7.0h， 生成 N-[4-[4-(ethylamino)butyl]phenyl]methanesulfonamide
  参考文献：
  名称：

  Progress toward the Development of a Safe and Effective Agent for Treating Reentrant Cardiac Arrhythmias:  Synthesis and Evaluation of Ibutilide Analogues with Enhanced Metabolic Stability and Diminished Proarrhythmic Potential

  摘要：

  A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.

  DOI：

  10.1021/jm0004289

文献信息

• 4-(4-METHANESULFONAMIDOPHENYL)BUTYLAMINE DERIVATIVES WITH ANTIARRHYTHMIC ACTIVITY
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0781273A1

  公开（公告）日：1997-07-02
• [EN] 4-(4-METHANESULFONAMIDOPHENYL)BUTYLAMINE DERIVATIVES WITH ANTIARRHYTHMIC ACTIVITY<br/>[FR] DERIVES 4-(4-METHANESULFONAMIDOPHENYL)BUTYLAMINE EXERÇANT UNE ACTIVITE ANTIARHYTHMIQUE
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：WO1996008471A1

  公开（公告）日：1996-03-21

  (EN) Methanesulfonamides are structurally depicted by formula (I), or its pharmacologically acceptable salts where R3 is a C1-7 alkyl substituted with C3-7 cycloalkyl, or a C1-10 alkyl substituted with one to eight fluorine atoms, one to three hydroxy, one to three C1-5 acyloxy or one to three C1-4 alkoxy substituents. These compounds are useful as Class III antiarrhythmic agents and are stable against rapid metabolism. Methods for treating cardiac arrhythmias with the compounds of formula (I) as well as compositions thereof are also described.(FR) Méthanesulfonamides de la formule (I), ou leurs sels pharmaceutiquement acceptables. Dans cette formule, R3 et un C1-7 alkyle substitué par un C3-7 cycloalkyle, ou un C1-10 alkyle substitué par 1 à 8 atomes de fluore, 1 à 3 substituants hydroxy, 1 à 3 substituants C1-5 acyloxy ou 1 à 3 substituants de C1-4 alcoxy. Ces composés se révèlent utiles comme agents antiarhythmiques de la classe III et se révèlent stables par rapport à un métabolisme rapide. L'invention porte également sur des méthodes de traitement des arhythmies cardiaques à l'aide de composés de la formule (I) ainsi que de compositions issues de ces composés.
• Progress toward the Development of a Safe and Effective Agent for Treating Reentrant Cardiac Arrhythmias:  Synthesis and Evaluation of Ibutilide Analogues with Enhanced Metabolic Stability and Diminished Proarrhythmic Potential
  作者：Jackson B. Hester、John K. Gibson、Lewis V. Buchanan、Madeline G. Cimini、Michael A. Clark、D. Edward Emmert、Michael A. Glavanovich、Rick J. Imbordino、Richelle J. LeMay、Moses W. McMillan、Salvatore C. Perricone、Donald M. Squires、Rodney R. Walters

  DOI：10.1021/jm0004289

  日期：2001.3.1

  A series of ibutilide analogues with fluorine substituents on the heptyl side chain was prepared and evaluated for class III antiarrhythmic activity, metabolic stability, and proarrhythmic potential. It was found that fluorine substituents stabilized the side chain to metabolic oxidation. Many of the compounds also retained the ability to increase the refractoriness of cardiac tissue at both slow and fast pacing rates. The potential for producing polymorphic ventricular tachycardia in the rabbit model was dependent on the chirality of the benzylic carbon. The S-enantiomers generally had less proarrhythmic activity than the corresponding racemates. One compound from this series (45E, trecetilide fumarate) had excellent antiarrhythmic activity and metabolic stability and was devoid of proarrhythmic activity in the rabbit model. It was chosen for further development.