2-Bromo-1-(3-bromo-5-nitrophenyl)ethanone | 145028-73-5

• 分子结构分类: 有机化合物 - 有机氧化合物
• 英文名称: 2-Bromo-1-(3-bromo-5-nitrophenyl)ethanone
• CAS: 145028-73-5
• 化学式: C₈H₅Br₂NO₃
• 分子量: 322.941
• InChiKey: UPKYMBHKOQJKQT-UHFFFAOYSA-N

物化性质

• 沸点：
  340.7±32.0 °C(Predicted)
• 密度：
  1.991±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.12
• 拓扑面积：
  62.9
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-Bromo-1-(3-bromo-5-nitrophenyl)ethanone 在 盐酸 、 sodium hydroxide 、 sodium tetrahydroborate 、 氯化亚砜 、 potassium carbonate 、 tin(ll) chloride 作用下， 以 甲醇 、 氯仿 、 水 、 丙酮 为溶剂， 反应 9.0h， 生成 N-[3-bromo-5-(2,3,5,6-tetrahydroimidazo[2,1-b][1,3]thiazol-6-yl)phenyl]-4-chlorobenzamide
  参考文献：
  名称：

  Synthesis and anti-filarial activity of 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazol[2,1-b]thiazole derivatives

  摘要：

  Structure-activity studies against filariae are described for a series of derivatives of 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (15) derivatives. In an in vivo assay using gerbils implanted with both Acanthocheilonema viteae and Brugia pahangi, the former parasite was shown to be the more sensitive to a range of amides of 15. None of these compounds, however, had any activity at 5 x 10(-5) mol against the worms in vitro suggesting that they required in vivo activation. This was confirmed when the benzamido derivative (6) was shown to be rapidly metabolised in gerbils to the parent amine (15). The latter had potent effects on filariae both in vivo and in vitro but was also found to be toxic to mammals and unsuitable for further development. Unsuccessful attempts to improve upon the therapeutic index of 15 through the synthesis of various novel analogues are described.

  DOI：

  10.1016/0223-5234(92)90184-3
• 作为产物：
  描述：

  3-溴-5-硝基苯甲酸 在 氯化亚砜 、 氢溴酸 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 2-Bromo-1-(3-bromo-5-nitrophenyl)ethanone
  参考文献：
  名称：

  Synthesis and anti-filarial activity of 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazol[2,1-b]thiazole derivatives

  摘要：

  Structure-activity studies against filariae are described for a series of derivatives of 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (15) derivatives. In an in vivo assay using gerbils implanted with both Acanthocheilonema viteae and Brugia pahangi, the former parasite was shown to be the more sensitive to a range of amides of 15. None of these compounds, however, had any activity at 5 x 10(-5) mol against the worms in vitro suggesting that they required in vivo activation. This was confirmed when the benzamido derivative (6) was shown to be rapidly metabolised in gerbils to the parent amine (15). The latter had potent effects on filariae both in vivo and in vitro but was also found to be toxic to mammals and unsuitable for further development. Unsuccessful attempts to improve upon the therapeutic index of 15 through the synthesis of various novel analogues are described.

  DOI：

  10.1016/0223-5234(92)90184-3

文献信息

• Synthesis and anti-filarial activity of 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazol[2,1-b]thiazole derivatives
  作者：JCW Comley、JP Court、WE Gutteridge、AT Hudson、DC Jenkins、DD Miller、RH Nicol、AW Randall、JN Stables、R Thornton

  DOI：10.1016/0223-5234(92)90184-3

  日期：1992.8

  Structure-activity studies against filariae are described for a series of derivatives of 6-(3-aminophenyl)-2,3,5,6-tetrahydroimidazo[2,1-b]thiazole (15) derivatives. In an in vivo assay using gerbils implanted with both Acanthocheilonema viteae and Brugia pahangi, the former parasite was shown to be the more sensitive to a range of amides of 15. None of these compounds, however, had any activity at 5 x 10(-5) mol against the worms in vitro suggesting that they required in vivo activation. This was confirmed when the benzamido derivative (6) was shown to be rapidly metabolised in gerbils to the parent amine (15). The latter had potent effects on filariae both in vivo and in vitro but was also found to be toxic to mammals and unsuitable for further development. Unsuccessful attempts to improve upon the therapeutic index of 15 through the synthesis of various novel analogues are described.