2-ethyl 7-methyl 3,6-dimethylquinoline-2,7-dicarboxylate | 1431530-71-0

• 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-ethyl 7-methyl 3,6-dimethylquinoline-2,7-dicarboxylate
• 英文别名: 2-O-ethyl 7-O-methyl 3,6-dimethylquinoline-2,7-dicarboxylate
• CAS: 1431530-71-0
• 化学式: C₁₆H₁₇NO₄
• 分子量: 287.315
• InChiKey: YPAQOQQAAUVKKD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.3
• 重原子数：
  21
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  65.5
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-ethyl 7-methyl 3,6-dimethylquinoline-2,7-dicarboxylate 在 sodium hydroxide 、 盐酸 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以35%的产率得到3,6-dimethylquinoline-2,7-dicarboxylic acid hydrochloride
  参考文献：
  名称：

  Identification of PDZ ligands by docking-based virtual screening for the development of novel analgesic agents

  摘要：

  Disrupting the interaction between the PDZ protein, PSD-95, and its target ligands (such as the glutamate NMDA receptor or the serotonin 5-HT2A receptor) was found to reduce hyperalgesia in various models of neuropathic pain. Here, we set out to identify lead molecules which would interact with PSD-95, and hence, would potentially display analgesic activity. We describe the virtual screening of the Asinex and Cambridge databases which together contain almost one million molecules. Using three successive docking filters and visual inspection, we identified three structural classes of molecules and synthesized a potential lead compound from each class. The binding of the molecules with the PDZ domains of PSD-95 was assessed by H-1-N-15 HSQC NMR experiments. The analgesic activity of the best ligand, quinoline 2, was evaluated in vivo in a model of neuropathic pain and showed promising results. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.100
• 作为产物：
  描述：

  乙醛酸乙酯 、 5-氨基-2-甲基苯甲酸甲酯 、 丙醛 在 magnesium sulfate 、 氧气 、 ytterbium(III) triflate 作用下， 以 氯仿 、 甲苯 为溶剂， 反应 19.0h， 以20%的产率得到2-ethyl 7-methyl 3,6-dimethylquinoline-2,7-dicarboxylate
  参考文献：
  名称：

  Identification of PDZ ligands by docking-based virtual screening for the development of novel analgesic agents

  摘要：

  Disrupting the interaction between the PDZ protein, PSD-95, and its target ligands (such as the glutamate NMDA receptor or the serotonin 5-HT2A receptor) was found to reduce hyperalgesia in various models of neuropathic pain. Here, we set out to identify lead molecules which would interact with PSD-95, and hence, would potentially display analgesic activity. We describe the virtual screening of the Asinex and Cambridge databases which together contain almost one million molecules. Using three successive docking filters and visual inspection, we identified three structural classes of molecules and synthesized a potential lead compound from each class. The binding of the molecules with the PDZ domains of PSD-95 was assessed by H-1-N-15 HSQC NMR experiments. The analgesic activity of the best ligand, quinoline 2, was evaluated in vivo in a model of neuropathic pain and showed promising results. (C) 2013 Published by Elsevier Ltd.

  DOI：

  10.1016/j.bmcl.2013.02.100

文献信息

• Identification of PDZ ligands by docking-based virtual screening for the development of novel analgesic agents
  作者：Naoual Bouzidi、Hemantkumar Deokar、Alexandre Vogrig、Benjamin Boucherle、Isabelle Ripoche、Isabelle Abrunhosa-Thomas、Liam Dorr、Anne-Sophie Wattiez、Lu-Yun Lian、Philippe Marin、Christine Courteix、Sylvie Ducki

  DOI：10.1016/j.bmcl.2013.02.100

  日期：2013.5

  Disrupting the interaction between the PDZ protein, PSD-95, and its target ligands (such as the glutamate NMDA receptor or the serotonin 5-HT2A receptor) was found to reduce hyperalgesia in various models of neuropathic pain. Here, we set out to identify lead molecules which would interact with PSD-95, and hence, would potentially display analgesic activity. We describe the virtual screening of the Asinex and Cambridge databases which together contain almost one million molecules. Using three successive docking filters and visual inspection, we identified three structural classes of molecules and synthesized a potential lead compound from each class. The binding of the molecules with the PDZ domains of PSD-95 was assessed by H-1-N-15 HSQC NMR experiments. The analgesic activity of the best ligand, quinoline 2, was evaluated in vivo in a model of neuropathic pain and showed promising results. (C) 2013 Published by Elsevier Ltd.