N-(6-chloropyridin-3-yl)-3-methoxybenzamide | 1293979-21-1

• 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-(6-chloropyridin-3-yl)-3-methoxybenzamide
• CAS: 1293979-21-1
• 化学式: C₁₃H₁₁ClN₂O₂
• 分子量: 262.696
• InChiKey: ZYRIVHRTTUIAJY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.076
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  2-氯-5-硝基吡啶 在 palladium 10% on activated carbon 、 氢气 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 为溶剂， 生成 N-(6-chloropyridin-3-yl)-3-methoxybenzamide
  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

• <i>N</i>-Pyridyl and Pyrimidine Benzamides as KCNQ2/Q3 Potassium Channel Openers for the Treatment of Epilepsy
  作者：George Amato、Rosemarie Roeloffs、Greg C. Rigdon、Brett Antonio、Theresa Mersch、Grant McNaughton-Smith、Alan D. Wickenden、Paul Fritch、Mark J. Suto

  DOI：10.1021/ml200053x

  日期：2011.6.9

  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.