(±)-2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 3-methylpiperidine-1-carbodithioate

• 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-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 3-methylpiperidine-1-carbodithioate
• 英文别名: [2-Hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl] 3-methylpiperidine-1-carbodithioate；[2-hydroxy-3-(2-methyl-5-nitroimidazol-1-yl)propyl] 3-methylpiperidine-1-carbodithioate
• 化学式: C₁₄H₂₂N₄O₃S₂
• 分子量: 358.486
• InChiKey: PBDSGXQJJPUKNT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  145
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  奥硝唑 在 sodium hydroxide 作用下， 以 二氯甲烷 、 水 、 丙酮 为溶剂， 反应 2.5h， 生成 (±)-2-hydroxy-3-(2-methyl-5-nitro-1H-imidazol-1-yl)propyl 3-methylpiperidine-1-carbodithioate
  参考文献：
  名称：

  2-Methyl-4/5-nitroimidazole derivatives potentiated against sexually transmitted Trichomonas : Design, synthesis, biology and 3D-QSAR study

  摘要：

  Trichomoniasis is the most prevalent, non-viral sexually transmitted diseases (STD) caused by amitochondriate protozoan Trichomonas vaginalis. Increased resistance of T. vaginalis to the marketed drug Metronidazole necessitates the development of newer chemical entities. A library of sixty 2-methyl-4/5-nitroimidazole derivatives was synthesized via nucleophilic ring opening reaction of epoxide and the efficacies against drug-susceptible and -resistant Trichomonas vaginalis were evaluated. All the molecules except two were found to be active against both susceptible and resistant strains with MICs ranging 8.55-336.70 mu M and 28.80-1445.08 mu M, respectively. Most of the compounds were remarkably more effective than the standard Metronidazole. This study analyzes the in vitro and in vivo activities of the new 5-nitroimidazoles, which were found to be safe against human cervical HeLa cells with good selectivity index. The exploration of SAR by the synthesis of four different prototypes and 3D-QSAR study has shown the importance of prototype 1 over other prototypes. (C) 2016 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2016.09.006