4-(6-Methoxy-pyridazin-3-yl)-piperazine-1-carboxylic acid (4-trifluoromethyl-phenyl)-amide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 4-(6-Methoxy-pyridazin-3-yl)-piperazine-1-carboxylic acid (4-trifluoromethyl-phenyl)-amide
• 英文别名: 4-(6-methoxypyridazin-3-yl)-N-[4-(trifluoromethyl)phenyl]piperazine-1-carboxamide
• 化学式: C₁₇H₁₈F₃N₅O₂
• 分子量: 381.357
• InChiKey: AEMAAXAECNGOFH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  70.6
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  3-氯-6-甲氧基哒嗪 在 三乙胺 作用下， 以 四氢呋喃 、 二甲基亚砜 为溶剂， 反应 8.0h， 生成 4-(6-Methoxy-pyridazin-3-yl)-piperazine-1-carboxylic acid (4-trifluoromethyl-phenyl)-amide
  参考文献：
  名称：

  Synthesis and evaluation of pyridazinylpiperazines as vanilloid receptor 1 antagonists

  摘要：

  A structurally biased chemical library of pyridazinylpiperazine analogs was prepared in an effort to improve the pharmaceutical and pharmacological profile of the lead compound N-(4-tertiarybutylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide (BCTC). The library was evaluated for VR1 antagonist activity in capsaicin-induced (CAP) and pH 5.5-induced (pH) FLIPR assays in a human VR1-expressing HEK293 cell line. The most potent VR1 antagonists were found to have IC50 values in the range of 9-200nM with improved pharmaceutical and pharmacological profiles versus the lead BCTC. These compounds represent possible second-generation BCTC analogs. (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2004.09.010

文献信息

• Synthesis and evaluation of pyridazinylpiperazines as vanilloid receptor 1 antagonists
  作者：Laykea Tafesse、Qun Sun、Lori Schmid、Kenneth J. Valenzano、Yakov Rotshteyn、Xin Su、Donald J. Kyle

  DOI：10.1016/j.bmcl.2004.09.010

  日期：2004.11

  A structurally biased chemical library of pyridazinylpiperazine analogs was prepared in an effort to improve the pharmaceutical and pharmacological profile of the lead compound N-(4-tertiarybutylphenyl)-4-(3-chloropyridin-2-yl)tetrahydropyrazine-1(2H)-carboxamide (BCTC). The library was evaluated for VR1 antagonist activity in capsaicin-induced (CAP) and pH 5.5-induced (pH) FLIPR assays in a human VR1-expressing HEK293 cell line. The most potent VR1 antagonists were found to have IC50 values in the range of 9-200nM with improved pharmaceutical and pharmacological profiles versus the lead BCTC. These compounds represent possible second-generation BCTC analogs. (C) 2004 Elsevier Ltd. All rights reserved.