N-[4-[4-[(6,6-difluorohexyl)ethylamino]-1-hydroxybutyl]phenyl]methanesulfonamide

• 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-[(6,6-difluorohexyl)ethylamino]-1-hydroxybutyl]phenyl]methanesulfonamide
• 英文别名: N-(4-(4-(Ethyl(6,6-difluorohexyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide；N-[4-[4-[ethyl(6,6-difluorohexyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide；N-[4-[4-[6,6-difluorohexyl(ethyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide
• 化学式: C₁₉H₃₂F₂N₂O₃S
• 分子量: 406.537
• InChiKey: HIOTUWOWMABMNE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  27
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  4-[(4-甲磺酰胺基)苯基]-4-氧代丁酸 在 lithium aluminium tetrahydride 、 碳酸氢钠 、 三乙胺 作用下， 以 四氢呋喃 、 乙腈 为溶剂， 反应 43.5h， 生成 N-[4-[4-[(6,6-difluorohexyl)ethylamino]-1-hydroxybutyl]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

• Antiarrhythmic methanesulfonamides
  申请人：The Upjohn Company

  公开号：US05405997A1

  公开（公告）日：1995-04-11

  Methanesulfonamides are structurally depicted by Formula I' ##STR1## or its pharmacologically acceptable salts where R.sub.3 is a C.sub.1-7 alkyl substituted with C.sub.3-7 cycloalkyl, or a C.sub.1-10 alkyl substituted with one to eight fluorine atoms, one to three hydroxy, one to three C.sub.1-5 acyloxy or one to three C.sub.1-4 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.

  甲磺酰胺类化合物结构如式I所示：##STR1##或其药理学上可接受的盐，其中R3为被C3-7环烷基取代的C1-7烷基，或被一至八个氟原子、一至三个羟基、一至三个C1-5酰氧基或一至三个C1-4烷氧基取代的C1-10烷基。这些化合物作为III类抗心律失常药物具有用途，并且对快速代谢稳定。还描述了使用式I化合物及其组合物治疗心律失常的方法。
• US5405997A
  申请人：——

  公开号：US5405997A

  公开（公告）日：1995-04-11