2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylpiperazine-1-carbodithioate | 52187-06-1

• 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-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylpiperazine-1-carbodithioate
• 英文别名: 4-methyl-piperazine-1-carbodithioic acid 2-(2-methyl-5-nitro-imidazol-1-yl)-ethyl ester；2-(2-methyl-5-nitro-1-imidazolyl)ethyl-4-methyl-1-piperazinylcarbodithioate；2-(2-Methyl-5-nitroimidazol-1-yl)ethyl 4-methylpiperazine-1-carbodithioate
• CAS: 52187-06-1
• 化学式: C₁₂H₁₉N₅O₂S₂
• 分子量: 329.447
• InChiKey: RKTBATAKNSHELG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  128
• 氢给体数：
  0
• 氢受体数：
  6

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 4-methyl-1-piperazinecarbodithioate 以 乙腈 为溶剂， 以65%的产率得到2-(2-methyl-5-nitro-1H-imidazol-1-yl)ethyl 4-methylpiperazine-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

• 2-(2-Methyl-5-nitro-1-imidazolyl)ethyl cycloaminocarbodithioates
  申请人：G. D. Searle & Co.

  公开号：US03954768A1

  公开（公告）日：1976-05-04

  2-(2-Methyl-5-nitro-1-imidazolyl)ethyl esters of cycloaminocarbodithioates are herein described. These compounds are anti-protozoal and anti-fungal agents. The compounds are prepared in 2 steps. The reaction of the appropriate cycloamine with carbon disulfide in aqueous base forms the aminocarbodithioate salt and the final products are formed by the reaction of this salt with 1-(2-chloroethyl)-2-methyl-5-nitroimidazole.

  本文介绍了环氨基羰基二硫酸酯的2-(2-甲基-5-硝基-1-咪唑基)乙基酯。这些化合物是抗原虫和抗真菌剂。这些化合物的制备有两个步骤。适当的环氨基与碳二硫化物在水性碱中反应形成氨基羰基二硫酸盐，最终产物由该盐与1-(2-氯乙基)-2-甲基-5-硝基咪唑反应形成。