2-Butyldisulfanyl-5-nitro-1H-benzoimidazole | 141400-51-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并咪唑类
• 英文名称: 2-Butyldisulfanyl-5-nitro-1H-benzoimidazole
• 英文别名: 2-(butyldisulfanyl)-6-nitro-1H-benzimidazole
• CAS: 141400-51-3
• 化学式: C₁₁H₁₃N₃O₂S₂
• 分子量: 283.375
• InChiKey: HVLFIELDKMLJLO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  18
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.36
• 拓扑面积：
  125
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  2-巯基-5-硝基苯并咪唑 、 2-n-butylmercaptoisothiourea hydrochloride 在 碳酸氢钠 作用下， 以 甲醇 、 水 为溶剂， 反应 1.0h， 以65%的产率得到2-Butyldisulfanyl-5-nitro-1H-benzoimidazole
  参考文献：
  名称：

  Synthesis and evaluation of imidazolyl disulfides for selective cytotoxicity to hypoxic EMT6 tumor cells in vitro

  摘要：

  Two series of disulfides were synthesized and evaluated in vitro for selective hypoxic tumor cell cytotoxicity using EMT6 cells. While the series of alkyl 5-nitrobenzimidazolyl disulfides displayed no selectivity, two alkyl imidazolyl disulfides, devoid of a nitro function, showed preferential toxicity to EMT6 cells treated under hypoxic conditions. Select agents of the alkyl imidazolyl series were found to deplete cellular glutathione (GSH) while the corresponding alkyl nitrobenzimidazolyl derivatives did not. One disulfide displaying selective hypoxic cell toxicity, n-butyl 2-imidazolyl disulfide, 10, caused significantly greater depletion of GSH under aerobic conditions. Removal of cellular GSH with buthionine sulfoximine (BSO) prior to exposure to 10 caused an increase in its toxicity and a loss of any differential between aerobic and hypoxic conditions. It is speculated that the diminished aerobic vs hypoxic toxicity of the agent toward EMT6 cells is due to a greater ability of 10 to interact with GSH under aerobic conditions as reflected by the greater GSH depletion.

  DOI：

  10.1016/0223-5234(92)90057-8

文献信息

• Synthesis and evaluation of imidazolyl disulfides for selective cytotoxicity to hypoxic EMT6 tumor cells in vitro
  作者：D Lynn Kirkpatrick、ML Jimale、KM King、T Chen

  DOI：10.1016/0223-5234(92)90057-8

  日期：1992.1

  Two series of disulfides were synthesized and evaluated in vitro for selective hypoxic tumor cell cytotoxicity using EMT6 cells. While the series of alkyl 5-nitrobenzimidazolyl disulfides displayed no selectivity, two alkyl imidazolyl disulfides, devoid of a nitro function, showed preferential toxicity to EMT6 cells treated under hypoxic conditions. Select agents of the alkyl imidazolyl series were found to deplete cellular glutathione (GSH) while the corresponding alkyl nitrobenzimidazolyl derivatives did not. One disulfide displaying selective hypoxic cell toxicity, n-butyl 2-imidazolyl disulfide, 10, caused significantly greater depletion of GSH under aerobic conditions. Removal of cellular GSH with buthionine sulfoximine (BSO) prior to exposure to 10 caused an increase in its toxicity and a loss of any differential between aerobic and hypoxic conditions. It is speculated that the diminished aerobic vs hypoxic toxicity of the agent toward EMT6 cells is due to a greater ability of 10 to interact with GSH under aerobic conditions as reflected by the greater GSH depletion.