Methyl 4-[(4-methoxyphenyl)methoxy]-6-(trifluoromethyl)quinoline-2-carboxylate | 1422284-65-8

• 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: Methyl 4-[(4-methoxyphenyl)methoxy]-6-(trifluoromethyl)quinoline-2-carboxylate
• 英文别名: methyl 4-[(4-methoxyphenyl)methoxy]-6-(trifluoromethyl)quinoline-2-carboxylate
• CAS: 1422284-65-8
• 化学式: C₂₀H₁₆F₃NO₄
• 分子量: 391.347
• InChiKey: YAAZMJDEJAVYJU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.2
• 拓扑面积：
  57.6
• 氢给体数：
  0
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  Methyl 4-[(4-methoxyphenyl)methoxy]-6-(trifluoromethyl)quinoline-2-carboxylate 在 氨 、 三乙胺 、 三氟乙酸酐 作用下， 生成 4-((4-methoxybenzyl)oxy)-6-(trifluoromethyl)quinoline-2-carbonitrile
  参考文献：
  名称：

  A novel series of N-(azetidin-3-yl)-2-(heteroarylamino)acetamide CCR2 antagonists

  摘要：

  The inflammatory response associated with the activation of C C chemokine receptor CCR2 via it's interaction with the monocyte chemoattractant protein-1 (MCP-1, CCL2) has been implicated in many disease states, including rheumatoid arthritis, multiple sclerosis, atherosclerosis, asthma and neuropathic pain. Small molecule antagonists of CCR2 have been efficacious in animal models of inflammatory disease, and have been advanced into clinical development. The necessity to attenuate hERG binding appears to be a common theme for many of the CCR2 antagonist scaffolds appearing in the literature, presumably due the basic hydrophobic motif present in all of these molecules. Following the discovery of a novel cyclohexyl azetidinylamide CCR2 antagonist scaffold, replacement of the amide bond with heterocyclic rings was explored as a strategy for reducing hERG binding and improving pharmacokinetic properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.017
• 作为产物：
  描述：

  4-甲氧基氯苄 、 methyl 1,4-dihydro-4-oxo-6-trifluoromethylquinoline-2-carboxylate 在 caesium carbonate 作用下， 生成 Methyl 4-[(4-methoxyphenyl)methoxy]-6-(trifluoromethyl)quinoline-2-carboxylate
  参考文献：
  名称：

  A novel series of N-(azetidin-3-yl)-2-(heteroarylamino)acetamide CCR2 antagonists

  摘要：

  The inflammatory response associated with the activation of C C chemokine receptor CCR2 via it's interaction with the monocyte chemoattractant protein-1 (MCP-1, CCL2) has been implicated in many disease states, including rheumatoid arthritis, multiple sclerosis, atherosclerosis, asthma and neuropathic pain. Small molecule antagonists of CCR2 have been efficacious in animal models of inflammatory disease, and have been advanced into clinical development. The necessity to attenuate hERG binding appears to be a common theme for many of the CCR2 antagonist scaffolds appearing in the literature, presumably due the basic hydrophobic motif present in all of these molecules. Following the discovery of a novel cyclohexyl azetidinylamide CCR2 antagonist scaffold, replacement of the amide bond with heterocyclic rings was explored as a strategy for reducing hERG binding and improving pharmacokinetic properties. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.12.017

文献信息

• A novel series of N-(azetidin-3-yl)-2-(heteroarylamino)acetamide CCR2 antagonists
  作者：Nalin L. Subasinghe、James Lanter、Thomas Markotan、Evan Opas、Sandra McKenney、Carl Crysler、Cuifen Hou、John O’Neill、Dana Johnson、Zhihua Sui

  DOI：10.1016/j.bmcl.2012.12.017

  日期：2013.2

  The inflammatory response associated with the activation of C C chemokine receptor CCR2 via it's interaction with the monocyte chemoattractant protein-1 (MCP-1, CCL2) has been implicated in many disease states, including rheumatoid arthritis, multiple sclerosis, atherosclerosis, asthma and neuropathic pain. Small molecule antagonists of CCR2 have been efficacious in animal models of inflammatory disease, and have been advanced into clinical development. The necessity to attenuate hERG binding appears to be a common theme for many of the CCR2 antagonist scaffolds appearing in the literature, presumably due the basic hydrophobic motif present in all of these molecules. Following the discovery of a novel cyclohexyl azetidinylamide CCR2 antagonist scaffold, replacement of the amide bond with heterocyclic rings was explored as a strategy for reducing hERG binding and improving pharmacokinetic properties. (C) 2012 Elsevier Ltd. All rights reserved.