N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide | 135124-45-7

• 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-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide
• 英文别名: N-[4-[4-[ethyl-(6-fluoro-6-methylheptyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide
• CAS: 135124-45-7
• 化学式: C₂₁H₃₇FN₂O₃S
• 分子量: 416.601
• InChiKey: RPQUKWBLAHJOPX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-hydroxybutyl)phenyl)methanesulfonamide 在 三氟乙酸 作用下， 生成 (E)-N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-1-butenyl)phenyl)methanesulfonamide
  参考文献：
  名称：

  Antiarrhythmic methanesulfonamides

  摘要：

  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。

  公开号：

  US05405997A1
• 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 41.5h， 生成 N-(4-(4-(Ethyl(6-fluoro-6-methylheptyl)amino)-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

• Compounds and methods for preparing methanesulfonamides
  申请人：MacKey Suzanne Sonja

  公开号：US20050148796A1

  公开（公告）日：2005-07-07

  A process for preparing (S)-(−)-N-[4-[4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxylphenyl]methanesulfonamide hemifumarate salt, which comprises reacting N-[4-[(2S)-tetrahydro-5-hydroxy-2-furanyl]phenyl]methanesulfonamide(IIa) with fluoroamine (III) in the presence of triacetoxyborohydride and ethyl acetate to provide [4-[-4-[ethyl(6-fluoro-6-methylheptyl)amino]-1-hydroxylphenyl]methanesulfonamide(I) and then converting I into the hemifumarate salt Ia. A process for preparing IIa is also claimed as well as intermediates IIa-IId.

  一种制备（S）-（-）-N- [4- [4- [乙基（6-氟-6-甲基庚基）氨基] -1-羟基苯基]甲烷磺酰胺半富马酸盐的方法，包括在三乙酰氧硼氢化钠和乙酸乙酯的存在下，将N- [4- [(2S) -四氢-5-羟基-2-呋喃基]苯基]甲烷磺酰胺（IIa）与氟胺（III）反应，以提供[4- [-4- [乙基（6-氟-6-甲基庚基）氨基] -1-羟基苯基]甲烷磺酰胺（I），然后将I转化为半富马酸盐Ia。还声明了制备IIa的方法以及中间体IIa-IId。
• ANTIARRHYTHMIC TERTIARY AMINE-ALKENYL-PHENYL-ALKANESULFONAMIDES
  申请人：THE UPJOHN COMPANY

  公开号：EP0484378A1

  公开（公告）日：1992-05-13
• ANTIARRHYTHMIC (S)-ENANTIOMERS OF METHANESULFONAMIDES
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP0802900B1

  公开（公告）日：2000-02-16
• COMPOUNDS AND METHODS FOR PREPARING METHANESULFONAMIDES
  申请人：PHARMACIA & UPJOHN COMPANY

  公开号：EP1395549A1

  公开（公告）日：2004-03-10
• US5405997A
  申请人：——

  公开号：US5405997A

  公开（公告）日：1995-04-11