3-acetyl-2-(4-ethylphenyl)-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-2,3-dihydro-1,3,4-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-acetyl-2-(4-ethylphenyl)-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-2,3-dihydro-1,3,4-oxadiazole
• 英文别名: 1-[2-(4-ethylphenyl)-5-[(2-methyl-5-nitroimidazol-1-yl)methyl]-2H-1,3,4-oxadiazol-3-yl]ethanone
• 化学式: C₁₇H₁₉N₅O₄
• 分子量: 357.369
• InChiKey: AYAVLVPFOTVBFA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  106
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  2-(2-methyl-5-nitro-1H-imidazol-1-yl)acetohydrazide 在 溶剂黄146 作用下， 以 乙醇 、 水 为溶剂， 反应 5.0h， 生成 3-acetyl-2-(4-ethylphenyl)-5-[(2-methyl-5-nitro-1H-imidazol-1-yl)methyl]-2,3-dihydro-1,3,4-oxadiazole
  参考文献：
  名称：

  Nitroimidazolyl hydrazones are better amoebicides than their cyclized 1,3,4-oxadiazoline analogues: In vitro studies and Lipophilic efficiency analysis

  摘要：

  Two series of compounds with hydrazone derivatives (HZ1-HZ12, series 1) and oxadiazoline derivatives (OZ1-OZ12, series 2) of the 2-methyl-5-nitro-1H-imidazole scaffold were designed and synthesized. Physicochemical properties and Lipophilic efficiency (LipE) analysis predicted higher intrinsic quality of the acylhydrazone derivatives (series 1) than their corresponding oxadiazoline analogues (series 2). In vitro antiamoebic results supported the above findings and validated that the acylhydrazone derivatives (HZ1-HZI2) show better activity than the oxadiazoline derivatives (OZ1-OZ12). MTT assay, using HepG2 cell line, revealed noncytotoxic nature of the compounds. The most promising results were observed for compounds HZ5 (IC50 = 0.96 mu M) and HZ9 (IC50 = 0.81 mu M) both in silico and in vitro. Analysis of the Lipophilic efficiency (LipE) of the compounds provided new insight for the design of potent and selective amoebicides. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.03.034