Α-溴代-4-硝基苯乙酮六次甲基四胺 | 91147-75-0

• 分子结构分类: 有机化合物 - 有机氧化合物
• 中文名称: Α-溴代-4-硝基苯乙酮六次甲基四胺
• 英文名称: 2-Bromo-1-(4-nitrophenyl)ethanone;1,3,5,7-tetrazatricyclo[3.3.1.13,7]decane
• CAS: 91147-75-0
• 化学式: C₆H₁₂N₄*C₈H₆BrNO₃
• 分子量: 384.233
• InChiKey: HTZXRTBMBHPQPT-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.15
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  75.8
• 氢给体数：
  0
• 氢受体数：
  7

制备方法与用途

生产方法 

用对硝基苯乙酮以溴素溴化，生成对硝基-α-溴代苯乙酮，然后与六亚甲基四胺成盐制得该品。

反应信息

• 作为反应物：
  描述：

  Α-溴代-4-硝基苯乙酮六次甲基四胺 在 盐酸 作用下， 以 乙醇 、 氯仿 为溶剂， 反应 72.0h， 以80%的产率得到2-氨基-1-(4-硝基苯基)乙酮盐酸盐
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

  摘要：

  The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Ttypanosoma cruzi in in vitro assays (IC50 < 57 mu M), and no mutagenic profile was observed in micro-nucleous tests. Although the in vitro inhibition test showed that 10-mu M doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.022
• 作为产物：
  描述：

  乌洛托品 、 2-溴-4'-硝基苯乙酮 以 氯仿 为溶剂， 反应 24.0h， 生成 Α-溴代-4-硝基苯乙酮六次甲基四胺
  参考文献：
  名称：

  Design, synthesis and biological evaluation of new aryl thiosemicarbazone as antichagasic candidates

  摘要：

  The present work reports on the synthesis, biological assaying and docking studies of a series of 12 aryl thiosemicarbazones, which were planned to act over two main enzymes, cruzain and trypanothione reductase. These enzymes are used as targets of trypanocidal activity in Chagas disease control with a minimal mutagenic profile. Three p-nitroaromatic thiosemicarbazones showed high activity against Ttypanosoma cruzi in in vitro assays (IC50 < 57 mu M), and no mutagenic profile was observed in micro-nucleous tests. Although the in vitro inhibition test showed that 10-mu M doses of eight compounds inhibited cruzain activity, no correlation was found between cruzain inhibition and trypanocidal activity. (C) 2013 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2013.04.022