2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(4-(4-nitrophenyl)piperazin-1-yl)propanoate | 1214752-95-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪烷类
• 英文名称: 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(4-(4-nitrophenyl)piperazin-1-yl)propanoate
• 英文别名: 2-(2-Methyl-5-nitroimidazol-1-yl)ethyl 3-[4-(4-nitrophenyl)piperazin-1-yl]propanoate
• CAS: 1214752-95-0
• 化学式: C₁₉H₂₄N₆O₆
• 分子量: 432.436
• InChiKey: FFCGMLNKIITNDX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  31
• 可旋转键数：
  8
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.47
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  9

反应信息

• 作为产物：
  描述：

  2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl acrylate 、 1-(4-硝基苯基)哌嗪 在 三乙胺 作用下， 以 二氯甲烷 、 1,2-二氯乙烷 为溶剂， 以66%的产率得到2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 3-(4-(4-nitrophenyl)piperazin-1-yl)propanoate
  参考文献：
  名称：

  Imidazole derivatives as possible microbicides with dual protection

  摘要：

  Twenty seven derivatives (2-28) of 2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethanol were synthesized and evaluated for anti-trichomonas, spermicidal and antifungal activities. Twenty six compounds were active against Trichomonas vaginalis at MIC ranging from 1-42 mu M and seven compounds (9,18,19,22,24,26,28) immobilized 100% human spermatozoa at 1% concentration (w/v). Twenty three compounds (2,3,5,8-26,28) exhibited antifungal activity at 25-50 mu g/mL concentration. Seven compounds (9,18,19,22,24,26,28) showed significant anti-trichomonas and spermicidal activities and also exhibited mild antifungal activity. All the compounds were highly safe towards human cervical cell line (HeLa) as shown by the cell-viability assay of HeLa cells at 200 mu g/mL concentration, whereas nonoxynol-9 (N-9, the marketed spermicidal microbicide) was highly cytotoxic. Therefore, it may be concluded that introduction of the pharmacophore responsible for spermicidal activity into a proven anti-trichomonas structure may lead to a potent dual function microbicide better and safer than N-9. (C) 2009 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2009.10.021