N-[4-[4-[(6,6-Difluoroheptyl)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-Difluoroheptyl)ethylamino]-1-hydroxybutyl]phenyl]methanesulfonamide
• 英文别名: N-[4-[4-[6,6-difluoroheptyl(ethyl)amino]-1-hydroxybutyl]phenyl]methanesulfonamide
• 化学式: C₂₀H₃₄F₂N₂O₃S
• 分子量: 420.564
• InChiKey: KZBHMKHBZOKLAW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  28
• 可旋转键数：
  14
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  78
• 氢给体数：
  2
• 氢受体数：
  7

上下游信息

• 上游原料

  中文名称	英文名称	CAS号	化学式	分子量
  ——	N-[4-[4-[(6,6-difluoroheptyl)ethylamino]-1,4-dioxobutyl]phenyl]methanesulfonamide	168268-65-3	C20H30F2N2O4S	432.532
  4-[(4-甲磺酰胺基)苯基]-4-氧代丁酸	4-<(methylsulfonyl)amino>-γ-oxobenzenebutanoic acid	100632-57-3	C11H13NO5S	271.294

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 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 反应 25.0h， 生成 N-[4-[4-[(6,6-Difluoroheptyl)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

• US5405997A
  申请人：——

  公开号：US5405997A

  公开（公告）日：1995-04-11