4-[1-(3-Chloro-2-methoxyphenyl)-5-(4-chlorophenyl)pyrazol-3-yl]-1-methylsulfonylpiperidine | 1383544-11-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-[1-(3-Chloro-2-methoxyphenyl)-5-(4-chlorophenyl)pyrazol-3-yl]-1-methylsulfonylpiperidine
• CAS: 1383544-11-3
• 化学式: C₂₂H₂₃Cl₂N₃O₃S
• 分子量: 480.415
• InChiKey: PDWGTPYJENVBGQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.6
• 重原子数：
  31
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  72.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  (3-chloro-2-methoxyphenyl)hydrazine 在 盐酸 、 四(三苯基膦)钯 、 sodium carbonate 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 乙醇 、 水 、 甲苯 为溶剂， 反应 2.75h， 生成 4-[1-(3-Chloro-2-methoxyphenyl)-5-(4-chlorophenyl)pyrazol-3-yl]-1-methylsulfonylpiperidine
  参考文献：
  名称：

  A novel series of pyrazolylpiperidine N-type calcium channel blockers

  摘要：

  Selective blockers of the N-type calcium channel have proven to be effective in animal models of chronic pain. However, even though intrathecally delivered synthetic x-conotoxin MVIIA from Conus magnus (ziconotide [Prialt (R)]) has been approved for the treatment of chronic pain in humans, its mode of delivery and narrow therapeutic window have limited its usefulness. Therefore, the identification of orally active, small-molecule N-type calcium channel blockers would represent a significant advancement in the treatment of chronic pain. A novel series of pyrazole-based N-type calcium channel blockers was identified by structural modification of a high-throughput screening hit and further optimized to improve potency and metabolic stability. In vivo efficacy in rat models of inflammatory and neuropathic pain was demonstrated by a representative compound from this series. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.075