N-isonicotinoyl-N'-[3'-(4'''-methylphenyl)-1'-phenyl-4'-pyrazolylmethylidene]hydrazine | 351988-52-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: N-isonicotinoyl-N'-[3'-(4'''-methylphenyl)-1'-phenyl-4'-pyrazolylmethylidene]hydrazine
• 英文别名: N-[[3-(4-methylphenyl)-1-phenylpyrazol-4-yl]methylideneamino]pyridine-4-carboxamide
• CAS: 351988-52-8
• 化学式: C₂₃H₁₉N₅O
• 分子量: 381.437
• InChiKey: QZXMUVPPXLWHMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  29
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.04
• 拓扑面积：
  72.2
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  N-isonicotinoyl-N'-[3'-(4'''-methylphenyl)-1'-phenyl-4'-pyrazolylmethylidene]hydrazine 在 碘苯二乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.0h， 以92%的产率得到4-(5-(1-phenyl-3-p-tolyl-1H-pyrazol-4-yl)-1,3,4-oxadiazol-2-yl)pyridine
  参考文献：
  名称：

  Synthesis of some pyrazolylaldehyde N-isonicotinoyl hydrazones and 2,5-disubstituted 1,3,4-oxadiazoles as DNA photocleaving agents

  摘要：

  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.

  DOI：

  10.1007/s00044-015-1340-x
• 作为产物：
  描述：

  4-methylacetophenone phenylhydrazone 在 溶剂黄146 、 三氯氧磷 作用下， 以 乙醇 为溶剂， 反应 11.5h， 生成 N-isonicotinoyl-N'-[3'-(4'''-methylphenyl)-1'-phenyl-4'-pyrazolylmethylidene]hydrazine
  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