4-(5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl)pyridine | 1610601-62-1

• 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-(5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl)pyridine
• 英文别名: 2-[3''-(4''''-fluorophenyl)-1''-phenylpyrazol-4''-yl]-5-(pyridin-4'-yl)-1,3,4-oxadiazole；2-[3-(4-Fluorophenyl)-1-phenylpyrazol-4-yl]-5-pyridin-4-yl-1,3,4-oxadiazole；2-[3-(4-fluorophenyl)-1-phenylpyrazol-4-yl]-5-pyridin-4-yl-1,3,4-oxadiazole
• CAS: 1610601-62-1
• 化学式: C₂₂H₁₄FN₅O
• 分子量: 383.384
• InChiKey: CGGVRZZLSSPNEE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.6
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  3-(4-氟-苯基)-1-苯基-1H-吡唑-4-甲醛 在 碘苯二乙酸 、 溶剂黄146 作用下， 以 乙醇 、 二氯甲烷 为溶剂， 反应 4.0h， 生成 4-(5-(3-(4-fluorophenyl)-1-phenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl)pyridine
  参考文献：
  名称：

  Design and synthesis of novel 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles as selective COX-2 inhibitors with potent anti-inflammatory activity

  摘要：

  A novel series of 2-phenyl-5-(1,3-diphenyl-1H-pyrazol-4-yl)-1,3,4-oxadiazoles were designed and synthesized for selective COX-2 inhibition with potent anti-inflammatory activity. Among the compounds tested, 9g (2-(3-(4-nitrophenyl)-1-phenyl-1H-pyrazol-4-yl)-5-phenyl-1,3,4-oxadiazole) was found to be the most potent inhibitor of COX-2 with IC50 of 0.31 μM showing promising degree of anti-inflammatory activity in the carrageenan-induced rat paw edema model with ED50 of 74.3 mg/kg. The lead compound 9g further showed suppression of acetic acid-induced writhes comparable to that of aspirin and gastro-sparing profile superior to the aspirin. Molecular docking analysis displayed higher binding affinity of ligands towards COX-2 than COX-1.

  DOI：

  10.1016/j.ejmech.2014.04.045

文献信息

• Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents
  作者：M. Kumar、V. Kumar、V. Beniwal

  DOI：10.1007/s00044-015-1340-x

  日期：2015.7

  In search of potential biologically active compounds, some novel 2,5-disubstituted 1,3,4-oxadiazole derivatives have been prepared conveniently via oxidation of newly synthesized pyrazolylaldehyde N-isonicotinoyl hydrazones by (diacetoxyiodo)benzene in dichloromethane under mild reaction conditions. Compounds were obtained in excellent yields, and their structures have been established on the basis of their FT-IR, H-1, C-13 NMR, and mass spectral data. The DNA photocleavage potential for all the synthesized compounds was evaluated using agarose gel electrophoresis. It has been observed that oxadiazole derivatives showed a significant level of DNA photocleavage activity when compared with their corresponding hydrazones, and some modifications in the basic structure may lead to construct some potential chemotherapeutic agents in future.