2-Ethynyl-4-(4-fluorophenyl)-5-pyridin-4-yl-1,3-oxazole | 1572047-39-2

• 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-Ethynyl-4-(4-fluorophenyl)-5-pyridin-4-yl-1,3-oxazole
• CAS: 1572047-39-2
• 化学式: C₁₆H₉FN₂O
• 分子量: 264.259
• InChiKey: VPZCYPYXRFRDLS-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.52
• 重原子数：
  20.0
• 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：
  38.92
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  2-Ethynyl-4-(4-fluorophenyl)-5-pyridin-4-yl-1,3-oxazole 在 sodium azide 、 copper(ll) sulfate pentahydrate 、 sodium ascorbate 作用下， 以 1,4-二氧六环 、 N-甲基吡咯烷酮 、 乙醇 、 水 为溶剂， 反应 0.33h， 以33%的产率得到4-[5-(4-fluorophenyl)-3-methyl-2-(2H-triazol-4-yl)imidazol-4-yl]pyridine
  参考文献：
  名称：

  Syntheses and structure–activity relationships for some triazolyl p38α MAPK inhibitors

  摘要：

  The design, synthesis and biological evaluation of novel triazolyl p38 alpha MAPK inhibitors with improved water solubility for formulation in cationic liposomes (SAINT-O-Somes) targeted at diseased endothelial cells is described. Water-solubilizing groups were introduced via a 'click' reaction of functional azides with 2-alkynyl imidazoles and isosteric oxazoles to generate two small libraries of 1,4-disubstituted 1,2,3-triazolyl p38 alpha MAPK inhibitors. Triazoles with low IC50 values and desired physicochemical properties were screened for in vitro downregulation of proinflammatory gene expression and were formulated in SAINT-O-Somes. Triazolyl p38 alpha MAPK inhibitor 88 (IC50 = 0.096 mu M) displayed the most promising in vitro activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.034
• 作为产物：
  描述：

  在 copper(l) iodide 、 四(三苯基膦)钯 、 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 为溶剂， 生成 2-Ethynyl-4-(4-fluorophenyl)-5-pyridin-4-yl-1,3-oxazole
  参考文献：
  名称：

  Syntheses and structure–activity relationships for some triazolyl p38α MAPK inhibitors

  摘要：

  The design, synthesis and biological evaluation of novel triazolyl p38 alpha MAPK inhibitors with improved water solubility for formulation in cationic liposomes (SAINT-O-Somes) targeted at diseased endothelial cells is described. Water-solubilizing groups were introduced via a 'click' reaction of functional azides with 2-alkynyl imidazoles and isosteric oxazoles to generate two small libraries of 1,4-disubstituted 1,2,3-triazolyl p38 alpha MAPK inhibitors. Triazoles with low IC50 values and desired physicochemical properties were screened for in vitro downregulation of proinflammatory gene expression and were formulated in SAINT-O-Somes. Triazolyl p38 alpha MAPK inhibitor 88 (IC50 = 0.096 mu M) displayed the most promising in vitro activity. (C) 2014 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2014.01.034