N-(2-氯嘧啶-5-基)-3-氟苯甲酰胺 | 582323-10-2

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: N-(2-氯嘧啶-5-基)-3-氟苯甲酰胺
• 英文名称: N-(2-chloropyrimidin-5-yl)-3-fluorobenzamide
• CAS: 582323-10-2
• 化学式: C₁₁H₇ClFN₃O
• 分子量: 251.647
• InChiKey: PVBHPXFLJOWZKI-UHFFFAOYSA-N

物化性质

• 沸点：
  346.0±22.0 °C(Predicted)
• 密度：
  1.472±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  17
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  54.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  间氟苯甲酸 在 吡啶 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.0h， 生成 N-(2-氯嘧啶-5-基)-3-氟苯甲酰胺
  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

• Pyrimidines as novel openers of potassium ion channels
  申请人：Icagen, Inc.

  公开号：US20030181465A1

  公开（公告）日：2003-09-25

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

  本发明提供了一类嘧啶酰胺，可用作钾离子通道的开启剂。该发明的化合物在治疗和诊断方法中均有用途。
• EP1483259A4
  申请人：——

  公开号：EP1483259A4

  公开（公告）日：2005-12-14
• PYRIMIDINES AS NOVEL OPENERS OF POTASSIUM ION CHANNELS
  申请人：Icagen, Inc.

  公开号：EP1483259A1

  公开（公告）日：2004-12-08
• US7205307B2
  申请人：——

  公开号：US7205307B2

  公开（公告）日：2007-04-17
• [EN] PYRIMIDINES AS NOVEL OPENERS OF POTASSIUM ION CHANNELS<br/>[FR] PYRIMIDINES UTILISEES COMME NOUVEAUX AGENTS D'OUVERTURE DES CANAUX IONIQUES DE POTASSIUM
  申请人：ICAGEN INC

  公开号：WO2003068767A1

  公开（公告）日：2003-08-21

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