4-(4-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoic acid | 1620085-57-5

• 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-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoic acid
• 英文别名: 4-[5-(4-fluorophenyl)-4-(2-oxo-1H-pyridin-4-yl)-1H-imidazol-2-yl]benzoic acid
• CAS: 1620085-57-5
• 化学式: C₂₁H₁₄FN₃O₃
• 分子量: 375.359
• InChiKey: LDYQHMPYEFIFBI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  28
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  95.1
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  4-(4-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoic acid 在 sodium hydroxide 作用下， 以 水 为溶剂， 反应 1.0h， 以100%的产率得到sodium 4-(4-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoate
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 4-fluorophenyl-imidazole p38α MAPK, CK1δ and JAK2 kinase inhibitors

  摘要：

  The synthesis and structure-activity relationships of novel 4-(4 '-fluorophenyl)imidazoles as selective p38 alpha MAPK, CK1 delta and JAK2 inhibitors with improved water solubility are described. Microwave-assisted multicomponent reactions afforded 4-fluorophenyl-2,5-disubstituted imidazoles. Carboxylate and phosphonate groups were introduced via 'click' reactions. The kinase selectivity was influenced by the heteroaryl group at imidazole C-5 and the position of a carboxylic acid or tetrazole at imidazole C-2. For example, pyrimidines 15 and 34 inhibited p38 alpha MAPK with IC50 = 250 nM and 96 nM, respectively. Pyridine 3 gave CK1 delta inhibition with IC50 = 89 nM and pyridin-2-one 31 gave JAK2 inhibition with IC50 = 62 nM. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.080
• 作为产物：
  描述：

  1-(4-fluorophenyl)-2-(2-oxo-1,2-dihydropyridin-4-yl)ethane-1,2-dione 、 对醛基苯甲酸 在 ammonium acetate 、 溶剂黄146 作用下， 反应 0.17h， 以100%的产率得到4-(4-(4-fluorophenyl)-5-(2-oxo-1,2-dihydropyridin-4-yl)-1H-imidazol-2-yl)benzoic acid
  参考文献：
  名称：

  Synthesis and structure–activity relationships of 4-fluorophenyl-imidazole p38α MAPK, CK1δ and JAK2 kinase inhibitors

  摘要：

  The synthesis and structure-activity relationships of novel 4-(4 '-fluorophenyl)imidazoles as selective p38 alpha MAPK, CK1 delta and JAK2 inhibitors with improved water solubility are described. Microwave-assisted multicomponent reactions afforded 4-fluorophenyl-2,5-disubstituted imidazoles. Carboxylate and phosphonate groups were introduced via 'click' reactions. The kinase selectivity was influenced by the heteroaryl group at imidazole C-5 and the position of a carboxylic acid or tetrazole at imidazole C-2. For example, pyrimidines 15 and 34 inhibited p38 alpha MAPK with IC50 = 250 nM and 96 nM, respectively. Pyridine 3 gave CK1 delta inhibition with IC50 = 89 nM and pyridin-2-one 31 gave JAK2 inhibition with IC50 = 62 nM. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.05.080