4-(4-pyridyl)-5-(4-fluorophenyl)-2-iodo-1H-imidazole | 1201526-49-9

• 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-pyridyl)-5-(4-fluorophenyl)-2-iodo-1H-imidazole
• CAS: 1201526-49-9
• 化学式: C₁₄H₉FIN₃
• 分子量: 365.148
• InChiKey: GBTHHEZEWKJLSD-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.88
• 重原子数：
  19.0
• 可旋转键数：
  2.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  41.57
• 氢给体数：
  1.0
• 氢受体数：
  2.0

反应信息

• 作为反应物：
  描述：

  4-(4-pyridyl)-5-(4-fluorophenyl)-2-iodo-1H-imidazole 、 phenyl(phenylethynyl)iodonium tosylate 在 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 为溶剂， 反应 2.5h， 以7%的产率得到4-(4-pyridyl)-5-(4-fluorophenyl)-2-iodo-1-phenylethynyl-1H-imidazole
  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
• 作为产物：
  描述：

  4-(4-pyridyl)-5-(4-fluorophenyl)-1-trityl-2-iodo-1H-imidazole 在 三氟乙酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以83%的产率得到4-(4-pyridyl)-5-(4-fluorophenyl)-2-iodo-1H-imidazole
  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