2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole
• 化学式: C₁₅H₈BrF₃N₂OS
• 分子量: 401.207
• InChiKey: PMSCRUQDRYJSKK-SOFGYWHQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 重原子数：
  23
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  67.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  (2E)-3-(5-溴(2-噻吩))-2-丙烯酸 在 1-丙基磷酸酐 、 三乙胺 、 三氯氧磷 作用下， 以 乙酸乙酯 为溶剂， 反应 1.0h， 生成 2-[(E)-2-(5-bromothiophen-2-yl)ethenyl]-5-[4-(trifluoromethyl)phenyl]-1,3,4-oxadiazole
  参考文献：
  名称：

  Novel 2-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,3,4-oxadiazole and 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole derivatives as dengue virus inhibitors targeting NS5 polymerase

  摘要：

  Using a functional high-throughput screening (HTS) and subsequent SAR studies, we have discovered a novel series of non-nucleoside dengue viral polymerase inhibitors. We report the elaboration of SAR around hit compound 1 as well as the synthesis and antiviral evaluation of 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole and 5-phenyl-2-[2-(2-thienyl)ethenyl]-1,3,4-oxadiazole analogues derived from a rapid and easily accessible chemical pathway. A large number of compounds prepared by this method were shown to possess in vitro activity against the polymerase of dengue virus. The most potent inhibitors were tested against Dengue virus clinical isolates on infected cells model and exhibit submicromolar activity on the four dengue virus serotypes. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.046

文献信息

• Novel 2-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,3,4-oxadiazole and 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole derivatives as dengue virus inhibitors targeting NS5 polymerase
  作者：Fatiha Benmansour、Cécilia Eydoux、Gilles Querat、Xavier de Lamballerie、Bruno Canard、Karine Alvarez、Jean-Claude Guillemot、Karine Barral

  DOI：10.1016/j.ejmech.2015.12.046

  日期：2016.2

  Using a functional high-throughput screening (HTS) and subsequent SAR studies, we have discovered a novel series of non-nucleoside dengue viral polymerase inhibitors. We report the elaboration of SAR around hit compound 1 as well as the synthesis and antiviral evaluation of 3-phenyl-5-[(E)-2-(thiophen-2-yl)ethenyl]-1,2,4-oxadiazole and 5-phenyl-2-[2-(2-thienyl)ethenyl]-1,3,4-oxadiazole analogues derived from a rapid and easily accessible chemical pathway. A large number of compounds prepared by this method were shown to possess in vitro activity against the polymerase of dengue virus. The most potent inhibitors were tested against Dengue virus clinical isolates on infected cells model and exhibit submicromolar activity on the four dengue virus serotypes. (C) 2016 Elsevier Masson SAS. All rights reserved.