1,3,5-tris(2-piperidin-1-ylethyl)-1,3,5-triazinane | 820241-36-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 哌啶类
• 英文名称: 1,3,5-tris(2-piperidin-1-ylethyl)-1,3,5-triazinane
• 英文别名: 1,3,5-Tris[2-(piperidin-1-yl)ethyl]-1,3,5-triazinane
• CAS: 820241-36-9
• 化学式: C₂₄H₄₈N₆
• 分子量: 420.685
• InChiKey: BGTQQTAUYNMTKB-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  30
• 可旋转键数：
  9
• 环数：
  4.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  19.4
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  N-{4-[2-(4-fluorophenyl)-2-hydroxyliminoacetyl]pyridin-2-yl}acetamide 、 1,3,5-tris(2-piperidin-1-ylethyl)-1,3,5-triazinane 以 乙醇 为溶剂， 反应 6.0h， 以76%的产率得到N-{4-[5-(4-fluorophenyl)-1-oxy-3-(2-(piperidin-1-yl)ethyl)-3H-imidazol-4-yl]pyridin-2-yl}acetamide
  参考文献：
  名称：

  Tetrasubstituted Imidazole Inhibitors of Cytokine Release:  Probing Substituents in the N-1 Position

  摘要：

  We prepared novel 1,2,4,5-tetrasubstituted imidazole derivatives with high anti-inflammatory activity by using our previously described regiospecific synthesis. Systematic optimization of the imidazole N-1 substituent resulted in compound 9b that potently inhibited the mitogen-activated protein kinase p38 (p38 IC50 = 0.218 muM) as well as the release of the proinflammatory cytokines interleukin-1beta (IL-1beta) and tumor necrosis factor alpha. (TNFalpha) from human whole blood after stimulation with LPS. Furthermore, compound 9b exhibited reduced cytochrome P450 interaction in comparison with SB203580. This result is particularly important, since cytochrome P450 interaction is observed for some p38 inhibitors and in turn can potentially cause drug-drug interaction or lead to other hepatic changes such as P450 enzyme induction.

  DOI：

  10.1021/jm0496584
• 作为产物：
  描述：

  聚合甲醛 、 1-(2-氨乙基)哌啶 以 甲醇 为溶剂， 生成 1,3,5-tris(2-piperidin-1-ylethyl)-1,3,5-triazinane
  参考文献：
  名称：

  基于全氢四氮杂四苯的新型多环加合物的合成

  摘要：

  通过全氢四氮杂四苯与甲醛和各种伯胺的一锅催化杂环化合成了手性中心为( R*,R*,R*,R* )构型的新型N,N'-二取代全氢六氮杂二苯并[fg,op]并四苯。胺以及1,3,5-三取代的1,3,5-三嗪与全氢四氮杂四苯的催化再环化反应。所有合成化合物的结构均通过核磁共振波谱和高分辨率质谱确认。

  DOI：

  10.1007/s11172-024-4353-0

文献信息

• Tetrasubstituted Imidazole Inhibitors of Cytokine Release:  Probing Substituents in the N-1 Position
  作者：Stefan A. Laufer、Werner Zimmermann、Kathrin J. Ruff

  DOI：10.1021/jm0496584

  日期：2004.12.1

  We prepared novel 1,2,4,5-tetrasubstituted imidazole derivatives with high anti-inflammatory activity by using our previously described regiospecific synthesis. Systematic optimization of the imidazole N-1 substituent resulted in compound 9b that potently inhibited the mitogen-activated protein kinase p38 (p38 IC50 = 0.218 muM) as well as the release of the proinflammatory cytokines interleukin-1beta (IL-1beta) and tumor necrosis factor alpha. (TNFalpha) from human whole blood after stimulation with LPS. Furthermore, compound 9b exhibited reduced cytochrome P450 interaction in comparison with SB203580. This result is particularly important, since cytochrome P450 interaction is observed for some p38 inhibitors and in turn can potentially cause drug-drug interaction or lead to other hepatic changes such as P450 enzyme induction.