4-(4-Methyl-pyridazin-3-yl)-piperazine-1-carboxylic acid (6-fluoro-benzothiazol-2-yl)-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-(4-Methyl-pyridazin-3-yl)-piperazine-1-carboxylic acid (6-fluoro-benzothiazol-2-yl)-amide
• 英文别名: N-(6-fluoro-1,3-benzothiazol-2-yl)-4-(4-methylpyridazin-3-yl)piperazine-1-carboxamide
• 化学式: C₁₇H₁₇FN₆OS
• 分子量: 372.426
• InChiKey: APVZULWOGLTJAJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.2
• 重原子数：
  26
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.29
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  3,6-二氯-4-甲基哒嗪 在 palladium on activated charcoal 氢气 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二甲基亚砜 为溶剂， 反应 11.0h， 生成 4-(4-Methyl-pyridazin-3-yl)-piperazine-1-carboxylic acid (6-fluoro-benzothiazol-2-yl)-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.