(E)-2-hydroxy-4-methyl-N'-(2-nitrobenzylidene)benzohydrazide

• 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: (E)-2-hydroxy-4-methyl-N'-(2-nitrobenzylidene)benzohydrazide
• 英文别名: 2-hydroxy-4-methyl-N-[(E)-(2-nitrophenyl)methylideneamino]benzamide
• 化学式: C₁₅H₁₃N₃O₄
• 分子量: 299.286
• InChiKey: MCQMPVGZUQUIQP-CXUHLZMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  22
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.07
• 拓扑面积：
  108
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  4-甲基水杨酸 在 硫酸 、 一水合肼 作用下， 以 乙醇 为溶剂， 反应 2.5h， 生成 (E)-2-hydroxy-4-methyl-N'-(2-nitrobenzylidene)benzohydrazide
  参考文献：
  名称：

  Synthesis, biological evaluation and molecular modeling studies of Schiff bases derived from 4-methylsalicylic acid as potential immunosuppressive agents

  摘要：

  A series of Schiff bases derived from 4-methylsalicylic acid (4a-4s) were synthesized, 14 of which (4a-4h, 4j-4l, 4n, 4q, and 4s) were reported for the first time. All the synthesized compounds were evaluated for their immunosuppressive activities for the first time. Among them, compound 4o displayed the most potent biological activity against lymph node cells (IC50 = 1.02 mu M for lymph node cells and IC50 = 2.17 mu M for PI3K gamma). The results of apoptosis and western-blot assays demonstrated that the immunosuppressive activity of compound 4o might be mediated by the inhibition of PI3K/AKT signaling pathway. Docking simulation was performed to position compound 4o into the PI3K gamma structure active site to determine the probable binding model.

  DOI：

  10.1007/s00044-013-0561-0

文献信息

• Synthesis, biological evaluation and molecular modeling studies of Schiff bases derived from 4-methylsalicylic acid as potential immunosuppressive agents
  作者：Ru Yan、Peng-Gang Liu、Zhi-Ming Zhang、Xian-Ying Fang、Xue-Wei Zhang、Jia-Li Deng、Hai-Liang Zhu

  DOI：10.1007/s00044-013-0561-0

  日期：2013.12

  A series of Schiff bases derived from 4-methylsalicylic acid (4a-4s) were synthesized, 14 of which (4a-4h, 4j-4l, 4n, 4q, and 4s) were reported for the first time. All the synthesized compounds were evaluated for their immunosuppressive activities for the first time. Among them, compound 4o displayed the most potent biological activity against lymph node cells (IC50 = 1.02 mu M for lymph node cells and IC50 = 2.17 mu M for PI3K gamma). The results of apoptosis and western-blot assays demonstrated that the immunosuppressive activity of compound 4o might be mediated by the inhibition of PI3K/AKT signaling pathway. Docking simulation was performed to position compound 4o into the PI3K gamma structure active site to determine the probable binding model.