N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylquinoline-3-carboxamide | 676557-29-2

• 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: N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylquinoline-3-carboxamide
• CAS: 676557-29-2
• 化学式: C₃₂H₃₂F₆N₂O₂Si
• 分子量: 618.694
• InChiKey: HXKCARPNNJLDND-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9.39
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  51.2
• 氢给体数：
  1
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylquinoline-3-carboxamide 、 碘甲烷 在 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 1.33h， 以70%的产率得到N-[3,5-bis(trifluoromethyl)benzyl]-2-[[(t-butyl)dimethylsilyloxy]methyl]-N-methyl-4-phenyl-3-quinolinecarboxamide
  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 咪唑 、 三甲基铝 作用下， 以 二氯甲烷 、 甲苯 为溶剂， 反应 2.66h， 生成 N-[[3,5-bis(trifluoromethyl)phenyl]methyl]-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-4-phenylquinoline-3-carboxamide
  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