diethyl (2-(4-(2-(4-fluorophenyl)-3-(2-(methylthio)pyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate | 1620085-48-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: diethyl (2-(4-(2-(4-fluorophenyl)-3-(2-(methylthio)pyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate
• 英文别名: 7-[1-(2-Diethoxyphosphorylethyl)triazol-4-yl]-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidine；7-[1-(2-diethoxyphosphorylethyl)triazol-4-yl]-2-(4-fluorophenyl)-3-(2-methylsulfanylpyrimidin-4-yl)imidazo[1,2-a]pyrimidine
• CAS: 1620085-48-4
• 化学式: C₂₅H₂₆FN₈O₃PS
• 分子量: 568.571
• InChiKey: FBUBDEOFMHAIPS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  39
• 可旋转键数：
  11
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.28
• 拓扑面积：
  148
• 氢给体数：
  0
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  diethyl (2-(4-(2-(4-fluorophenyl)-3-(2-(methylthio)pyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate 在 sodium hydroxide 作用下， 以 甲醇 、 水 为溶剂， 生成
  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：

  2-溴乙基膦酸二乙酯 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 四丁基溴化铵 、 sodium ascorbate 作用下， 以 四氢呋喃 、 乙醇 、 水 为溶剂， 反应 120.0h， 生成 diethyl (2-(4-(2-(4-fluorophenyl)-3-(2-(methylthio)pyrimidin-4-yl)imidazo[1,2-a]pyrimidin-7-yl)-1H-1,2,3-triazol-1-yl)ethyl)phosphonate
  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