4-(4-fluorophenyl)-5-[2-(1-phenylethylamino)pyridin-4-yl]-1,3-dihydroimidazol-2-one | 1229571-94-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-fluorophenyl)-5-[2-(1-phenylethylamino)pyridin-4-yl]-1,3-dihydroimidazol-2-one
• CAS: 1229571-94-1
• 化学式: C₂₂H₁₉FN₄O
• 分子量: 374.417
• InChiKey: SIFWKCGECONQHE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  28
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.09
• 拓扑面积：
  66
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  3-[4-(4-fluorophenyl)-5-(2-fluoropyridin-4-yl)-1H-imidazol-2-ylthio]propane-1,2-diol 、 α-苯乙胺 反应 7.0h， 以25%的产率得到4-(4-fluorophenyl)-5-[2-(1-phenylethylamino)pyridin-4-yl]-1,3-dihydroimidazol-2-one
  参考文献：
  名称：

  Unexpected Reaction of 2-Alkylsulfanylimidazoles to Imidazol-2-ones: Pyridinylimidazol-2-ones as Novel Potent p38α Mitogen-Activated Protein Kinase Inhibitors

  摘要：

  While optimizing the synthesis of 2-alkylsulfanyl-5-(2-aminopyridin-4-yl)imidazoles, we identified an unexpected reaction to pyridinylimidazol-2-ones. 2-Alkylsulfanylimidazoles, bearing a 2-hydroxyethyl or a 2,3-dihydroxypropyl moiety at the imidazole C2-S position, were converted by heating into imidazol-2-ones. These imidazol-2-ones were tested for their ability to inhibit p38 alpha MAP kinase and LPS-stimulated TNF-alpha release in HWB. Introduction of an amino moiety at the pyridine C2 position led to compounds showing potent enzyme inhibitory activity with double-digit nanomolar IC50 values (5a: IC50 = 23 nM).

  DOI：

  10.1021/jm100161q