2-(4-fluorophenyl)-3-(4-pyridyl)-5-chloro-(2-hydroxyethyl)imidazo[1,2-a]pyridine | 1201526-69-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 2-(4-fluorophenyl)-3-(4-pyridyl)-5-chloro-(2-hydroxyethyl)imidazo[1,2-a]pyridine
• 英文别名: 2-[5-Chloro-2-(4-fluorophenyl)-3-pyridin-4-ylimidazo[1,2-a]pyridin-7-yl]ethanol
• CAS: 1201526-69-3
• 化学式: C₂₀H₁₅ClFN₃O
• 分子量: 367.81
• InChiKey: BTVZYVFJLRSSCW-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  50.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  4-(4-fluorophenyl)-5-(4-pyridyl)-1-ethynyl-2-(4-hydroxybut-1-ynyl)-1H-imidazole 在 四甲基氯化铵 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 120.0h， 以50%的产率得到2-(4-fluorophenyl)-3-(4-pyridyl)-5-chloro-(2-hydroxyethyl)imidazo[1,2-a]pyridine
  参考文献：
  名称：

  Synthesis and biological evaluation of p38α kinase-targeting dialkynylimidazoles

  摘要：

  Based on the mild, thermal rearrangement of 1,2-dialkynylimidazoles to reactive carbene or diradical intermediates, a series of 1,2-dialkynylimidazoles were designed as potential irreversible p38 MAP kinase a-isoform (p38 alpha) inhibitors. The synthesis of these dialkynylimidazoles and their kinase inhibition activity is reported. The 1-ethynyl-substituted dialkynylimidazole 14 is a potent (IC50 = 200 nM) and selective inhibitor of p38 alpha. Moreover, compound 14 covalently modifies p38 alpha as determined by ESI-MS after 12 h incubation at 37 degrees C. The unique kinase inhibition, covalent kinase adduct formation, and minimal CYP450 2D6 inhibition by compound 14 demonstrate that dialkynylimidazoles are a new, promising class of p38 alpha inhibitors. (C) 2009 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2009.09.094