2-(pyridin-2-ylethynyl)quinolin-5-yl pivalate | 1423778-48-6

• 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: 2-(pyridin-2-ylethynyl)quinolin-5-yl pivalate
• 英文别名: 2-(pyridine-2-ylethynyl)quinoline-5-yl pivalate；[2-(2-Pyridin-2-ylethynyl)quinolin-5-yl] 2,2-dimethylpropanoate；[2-(2-pyridin-2-ylethynyl)quinolin-5-yl] 2,2-dimethylpropanoate
• CAS: 1423778-48-6
• 化学式: C₂₁H₁₈N₂O₂
• 分子量: 330.386
• InChiKey: UKACSZVQRLENQA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  52.1
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2-(pyridin-2-ylethynyl)quinolin-5-yl pivalate 在 lithium aluminium tetrahydride 作用下， 以 四氢呋喃 为溶剂， 反应 0.5h， 以9%的产率得到2-(pyridine-2-ylethynyl)quinoline-5-ol
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain

  摘要：

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.056
• 作为产物：
  描述：

  5-羟基喹啉 在 吡啶 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 三乙胺 、 间氯过氧苯甲酸 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 47.5h， 生成 2-(pyridin-2-ylethynyl)quinolin-5-yl pivalate
  参考文献：
  名称：

  Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain

  摘要：

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.056

文献信息

• Synthesis and biological evaluation of 2-(arylethynyl)quinoline derivatives as mGluR5 antagonists for the treatment of neuropathic pain
  作者：Myung-Hee Son、Ji Young Kim、Eun Jeong Lim、Du-Jong Baek、Kihang Choi、Jae Kyun Lee、Ae Nim Pae、Sun-Joon Min、Yong Seo Cho

  DOI：10.1016/j.bmcl.2012.12.056

  日期：2013.3

  We described here the synthesis and biological evaluation of mGluR5 antagonists containing a quinoline ring structure. Using intracellular calcium mobilization assay (FDSS assay), we identified compound 5n, showing high inhibitory activity against mGluR5. In addition, it was found that compound 5n has excellent stability profile. Finally, this compound exhibited favorable analgesic effects in spinal nerve ligation model of neuropathic pain, which is comparable to gabapentin. (c) 2012 Elsevier Ltd. All rights reserved.