3-(2-phenylvinyl)-5-methyl-1,2,4-oxadiazole

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(2-phenylvinyl)-5-methyl-1,2,4-oxadiazole
• 英文别名: 5-phenyl-3-(2-phenylethenyl)-1,2,4-oxadiazole
• 化学式: C₁₆H₁₂N₂O
• 分子量: 248.284
• InChiKey: QQTGNBLHZXQAGP-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.91
• 重原子数：
  19.0
• 可旋转键数：
  3.0
• 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

• 作为产物：
  描述：

  (肉)桂腈 在 盐酸羟胺 、 magnesium oxide 、 sodium carbonate 作用下， 以 乙醇 为溶剂， 反应 0.02h， 生成 3-(2-phenylvinyl)-5-methyl-1,2,4-oxadiazole
  参考文献：
  名称：

  One-Pot Synthesis of 1,2,4-Oxadiazoles Mediated by Microwave Irradiation under Solvent-Free Condition

  摘要：

  Microwave-assisted synthesis of 1,2,4-oxadiazoles of amidoximes under solvent free conditions was found to be an efficient method for one-pot synthesis of 1,2,4-oxadiazole derivatives from amidoximes and acyl chlorides. This method is an easy, rapid, and high-yielding reaction for the synthesis of 1,2,4-oxadiazoles.

  DOI：

  10.3987/com-03-9769

文献信息

• Synthesis and evaluation of 1,2,4-oxadiazole derivatives as potential anti-inflammatory agents by inhibiting NF-κB signaling pathway in LPS-stimulated RAW 264.7 cells
  作者：Yu-Ying Zhang、Qian-Qian Zhang、Juan Zhang、Jia-Li Song、Jia-Cheng Li、Ke Han、Jin-Tian Huang、Cheng-Shi Jiang、Hua Zhang

  DOI：10.1016/j.bmcl.2020.127373

  日期：2020.9

  In this study, a series of compounds with 1,2,4-oxadiazole core was designed and synthesized for the optimi-zation of JC01, an anti-inflammatory hit identified from our in-house compound library using NF-xB pathway luciferase assay and NO production assay. All the synthetic compounds 1-29 have been screened for their anti-inflammatory effects by evaluating their inhibition against LPS-induced NO release, and compound 17 exhibited the highest activity. Western blotting and immunofluorescence analysis revealed that 17 prominently inhibited LPS-induced activation of NF-kappa B in RAW264.7 cells and blocked the phosphorylation of p65. Consistent with these results, it was found that 17 prevented the nuclear translocation of NF-kappa B induced by LPS. These data highlighted 17 as a promising anti-inflammatory agent by inhibiting NF-kappa B activity.