2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-phenyl-quinoline-3-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide | 676557-28-1

• 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-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-phenyl-quinoline-3-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide
• 英文别名: N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[(1,3-dioxoisoindol-2-yl)methyl]-4-phenylquinoline-3-carboxamide
• CAS: 676557-28-1
• 化学式: C₃₄H₂₁F₆N₃O₃
• 分子量: 633.549
• InChiKey: TZBLHTJIWAJSOK-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.9
• 重原子数：
  46
• 可旋转键数：
  6
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  79.4
• 氢给体数：
  1
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-phenyl-quinoline-3-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide 在 一水合肼 作用下， 以 乙醇 为溶剂， 反应 4.0h， 以85%的产率得到2-Aminomethyl-4-phenyl-quinoline-3-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide
  参考文献：
  名称：

  A Non-Peptide NK₁ Receptor Agonist Showing Subpicomolar Affinity

  摘要：

  3-Quinolinecarboxamides have been synthesized and evaluated for their binding to the human NK1 receptor. Several secondary amide derivatives show NK1 receptor affinity in the picomolar range. The most active compound, hydroxymethylcarboxamide 3h showing an IC50 value in the subpicomolar range, behaved as an agonist of NK1 receptor in endothelial cell proliferation, inositol phosphate turnover, and NO-mediated cyclic GMP accumulation, thus proving it to be the first non-peptide NK, receptor agonist showing very high potency.

  DOI：

  10.1021/jm034219a
• 作为产物：
  描述：

  9-phenylfuro[3,4-b]quinolin-1(3H)-one 在 三甲基铝 、 三溴化磷 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 3.33h， 生成 2-(1,3-Dioxo-1,3-dihydro-isoindol-2-ylmethyl)-4-phenyl-quinoline-3-carboxylic acid 3,5-bis-trifluoromethyl-benzylamide
  参考文献：
  名称：

  A Non-Peptide NK₁ Receptor Agonist Showing Subpicomolar Affinity

  摘要：

  3-Quinolinecarboxamides have been synthesized and evaluated for their binding to the human NK1 receptor. Several secondary amide derivatives show NK1 receptor affinity in the picomolar range. The most active compound, hydroxymethylcarboxamide 3h showing an IC50 value in the subpicomolar range, behaved as an agonist of NK1 receptor in endothelial cell proliferation, inositol phosphate turnover, and NO-mediated cyclic GMP accumulation, thus proving it to be the first non-peptide NK, receptor agonist showing very high potency.

  DOI：

  10.1021/jm034219a