2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl dimethylcarbamodithioate | 52187-12-9

• 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-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl dimethylcarbamodithioate
• 英文别名: dimethyl-dithiocarbamic acid 2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl ester；Imidazole1dimethyldithiocarbamoylethyl2methyl5NI；2-(2-methyl-5-nitroimidazol-1-yl)ethyl N,N-dimethylcarbamodithioate
• CAS: 52187-12-9
• 化学式: C₉H₁₄N₄O₂S₂
• 分子量: 274.368
• InChiKey: RWHTVHBQIGVAAR-UHFFFAOYSA-N

物化性质

• 熔点：
  109-110 °C
• 沸点：
  453.4±51.0 °C(Predicted)
• 密度：
  1.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  17
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  124
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-甲基-5-硝基-1H-咪唑-1-乙基甲磺酸酯 、 sodium dimethyldithiocarbamate 以 乙腈 为溶剂， 以79%的产率得到2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl dimethylcarbamodithioate
  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