N-(6-chloropyridin-3-yl)-3-fluoro-4-(4-fluorophenyl)sulfanylbenzamide | 378241-28-2

• 分子结构分类: 有机化合物 - 有机硫化合物 - 硫醚类
• 英文名称: N-(6-chloropyridin-3-yl)-3-fluoro-4-(4-fluorophenyl)sulfanylbenzamide
• CAS: 378241-28-2
• 化学式: C₁₈H₁₁ClF₂N₂OS
• 分子量: 376.814
• InChiKey: RGODQEBGKZESJG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.9
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.3
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-Fluoro-4-(4-fluorophenyl)sulfanylbenzoic acid 在 草酰氯 、 N,N-二异丙基乙胺 、 N,N-二甲基甲酰胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(6-chloropyridin-3-yl)-3-fluoro-4-(4-fluorophenyl)sulfanylbenzamide
  参考文献：
  名称：

  N-Pyridyl and Pyrimidine Benzamides as KCNQ2/Q3 Potassium Channel Openers for the Treatment of Epilepsy

  摘要：

  A series of N-pyridyl benzamide KCNQ2/Q3 potassium channel openers were identified and found to be active in animal models of epilepsy and pain. The best compound 12 [ICA-027243, N-(6-chloro-pyridin-3-yl)-3,4-difluoro-benzamide] has an EC(50) of 0.38 mu M and is selective for KCNQ2/Q3 channels. This compound was active in several rodent models of epilepsy and pain but upon repeated dosing had a number of unacceptable toxicities that prevented further development. On the basis of the structure activity relationships developed around 12, a second compound, 51, [N-(2-chloro-pyrimidin-5-yl)-3,4-difluoro-benzamide, ICA-069673], was prepared and advanced into a phase 1 clinical study. Herein, we describe the structure activity relationships that led to the identification of compound 12 and to the corresponding pyrimidine 51.

  DOI：

  10.1021/ml200053x

文献信息

• Pyridine-substituted benzanilides as potassium ion channel openers
  申请人：——

  公开号：US20010049444A1

  公开（公告）日：2001-12-06

  The present invention provides a genus of pyridine-substituted benzanilides that are useful as openers of potassium ion channels. The compounds of the invention are of use in both therapeutic and diagnostic methods.

  本发明提供了一类取代吡啶基苯甲酰苯胺的属，这些属可作为钾离子通道的开启剂。本发明的化合物在治疗和诊断方法中均有用途。
• PYRIDINE-SUBSTITUTED BENZANILIDES AS POTASSIUM ION CHANNEL OPENERS
  申请人：Icagen, Inc.

  公开号：EP1363884A2

  公开（公告）日：2003-11-26
• EP1363884A4
  申请人：——

  公开号：EP1363884A4

  公开（公告）日：2005-03-30
• US6495550B2
  申请人：——

  公开号：US6495550B2

  公开（公告）日：2002-12-17
• [EN] PYRIDINE-SUBSTITUTED BENZANILIDES AS POTASSIUM ION CHANNEL OPENERS<br/>[FR] BENZANILIDES A SUBSTITUTION PYRIDINE UTILISES COMME OUVREURS DE CANAUX IONIQUES DE POTASSIUM
  申请人：ICAGEN INC

  公开号：WO2002062295A2

  公开（公告）日：2002-08-15

  The present invention provides a genus of pyridine-substituted benzanilides that are useful as openers of potassium ion channels. The compounds of the invention are of use in both therapeutic and diagnostic methods.