2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-(pyridin-2-yl)piperazine-1-carbodithioate | 1214752-98-3

• 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 4-(pyridin-2-yl)piperazine-1-carbodithioate
• 英文别名: 2-(2-Methyl-5-nitroimidazol-1-yl)ethyl 4-pyridin-2-ylpiperazine-1-carbodithioate
• CAS: 1214752-98-3
• 化学式: C₁₆H₂₀N₆O₂S₂
• 分子量: 392.506
• InChiKey: KENYRRNJKYASQY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  26
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  140
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  sodium 4-(pyridin-2-yl)piperazine-1-carbodithioate 、 2-甲基-5-硝基-1H-咪唑-1-乙基甲磺酸酯 以 乙腈 为溶剂， 以65%的产率得到2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-(pyridin-2-yl)piperazine-1-carbodithioate
  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

文献信息

• Imidazole derivatives as possible microbicides with dual protection
  作者：Lalit Kumar、Amit Sarswat、Nand Lal、Vishnu L. Sharma、Ashish Jain、Rajeev Kumar、Vikas Verma、Jagdamba P. Maikhuri、Awanit Kumar、Praveen K. Shukla、Gopal Gupta

  DOI：10.1016/j.ejmech.2009.10.021

  日期：2010.2

  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.