3-[2-(6-methylpyridin-2-yl)ethynyl]quinoline

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 3-[2-(6-methylpyridin-2-yl)ethynyl]quinoline
• 化学式: C₁₇H₁₂N₂
• 分子量: 244.296
• InChiKey: QWQVAXTXUSUWHX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.34
• 重原子数：
  19.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.06
• 拓扑面积：
  25.78
• 氢给体数：
  0.0
• 氢受体数：
  2.0

反应信息

• 作为产物：
  描述：

  三甲基-[2-(6-甲基吡啶-2-基)乙炔基]锡烷 、 3-溴喹啉 在 四(三苯基膦)钯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 以82%的产率得到3-[2-(6-methylpyridin-2-yl)ethynyl]quinoline
  参考文献：
  名称：

  Synthesis and receptor assay of aromatic–ethynyl–aromatic derivatives with potent mGluR5 antagonist activity

  摘要：

  Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2004.09.042

文献信息

• Synthesis and receptor assay of aromatic–ethynyl–aromatic derivatives with potent mGluR5 antagonist activity
  作者：David Alagille、Ronald M. Baldwin、Bryan L. Roth、Jarda T. Wroblewski、Ewa Grajkowska、Gilles D. Tamagnan

  DOI：10.1016/j.bmc.2004.09.042

  日期：2005.1

  Noncompetitive antagonists of the human metabotropic glutamate receptor subtype 5 (mGluR5) have been implicated as potential therapeutics for the treatment of a variety of nervous system disorders, including pain, anxiety, and drug addiction. To discover novel noncompetitive antagonists to the mGluR5, we initiated an SAR study around the known lead compounds MPEP and M-MPEP. Our results pointed out the critical role of the para position of the two aromatic rings, which leads to inactive products and permitted the discovery of potent mGluR5 antagonists (e.g., 16, 25, 28, 34 IC50 = 13.5, 11.9, 21, 15nM, respectively). (C) 2004 Elsevier Ltd. All rights reserved.