(2-chloro-benzylidene)-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]amine | 1345511-32-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: (2-chloro-benzylidene)-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]amine
• 英文别名: 1-(2-chlorophenyl)-N-[2-(2-methyl-5-nitroimidazol-1-yl)ethyl]methanimine
• CAS: 1345511-32-1
• 化学式: C₁₃H₁₃ClN₄O₂
• 分子量: 292.725
• InChiKey: SMXXYSPRIGMCMA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  76
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  2-氯苯甲醛 、 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80%的产率得到(2-chloro-benzylidene)-[2-(2-methyl-5-nitro-imidazol-1-yl)ethyl]amine
  参考文献：
  名称：

  Synthesis, characterization and biological activity of Schiff bases derived from metronidazole

  摘要：

  A series of novel Schiff bases; compounds 3a-j were prepared by reacting 1-(2-aminoethyl)-2-methyl-5-nitroimidazole dihydrochloride monohydrate (1) with different aldehydes. The structures of these compounds were confirmed through different spectroscopic methods such as H-1-NMR, C-13-NMR and mass spectrometry and also by elemental analyses. The prepared compounds were evaluated in vitro for their antigiardial, antibacterial and antifungal activities. Compounds 3h, 3b and 3d showed remarkable antigiardial activities and were found to be more active than metronidazole with IC50 of 0.83, 1.36 and 1.83 mu M, respectively. Other compounds also exhibited antigiardial activity and were as good as or even more potent than metronidazole. Some of the newly synthesized Schiff bases exhibited more antifungal activities than the parent drug. In addition, a few of the prepared compounds exhibited modest antibacterial activity but were not as active as metronidazole.

  DOI：

  10.1007/s00044-011-9830-y