2-溴-4-(2-噻吩基)噻唑 | 1125409-90-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 中文名称: 2-溴-4-(2-噻吩基)噻唑
• 英文名称: 2-Bromo-4-(2-thienyl)thiazole
• 英文别名: 2-bromo-4-thiophen-2-yl-1,3-thiazole
• CAS: 1125409-90-6
• 化学式: C₇H₄BrNS₂
• 分子量: 246.151
• InChiKey: XRXGEQOSIYEEKD-UHFFFAOYSA-N

物化性质

• 沸点：
  330.2±17.0 °C(Predicted)
• 密度：
  1.720±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.4
• 重原子数：
  11
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  69.4
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  2-乙炔噻吩 、 2-溴-4-(2-噻吩基)噻唑 在 copper(l) iodide 、 sodium azide 、 N,N'-二甲基乙二胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 以60%的产率得到4-(thiophen-2-yl)-1-(4-(thiophen-2-yl)thiazol-2-yl)-1H-1,2,3-triazole
  参考文献：
  名称：

  One-Pot Tandem Copper-Catalyzed Library Synthesis of 1-Thiazolyl-1,2,3-triazoles as Anticancer Agents

  摘要：

  One-pot multicomponent synthesis to assemble compounds has been an efficient method for constructing a compound library. We have developed one-pot tandem copper-catalyzed azidation and CuAAC reactions that afford 1-thiazolyl-1,2,3-triazoles with anticancer activity. By utilizing this one-pot synthetic strategy, we constructed a library of 1-thiazolyl-1,2,3-triazoles in search of the potent lead compound. Furthermore, 1-thiazolyl-1,2,3-triazoles were evaluated for anticancer activity against the multidrug-resistant cancer cells MES-SA/Dx5. Most of the 1-thiazolyl-1,2,3-triazoles revealed cytotoxic effect against cancer cells at micromolar to low micromolar range. Testing some of the most potent compounds (5{4,2-4} and 5{5,1-3}) against the normal cell line Vero showed no significant toxicity (except 5{4,2}) to normal cells. This result indicates that compounds 5{4,3-4} and 5{5,1-3} possessed good potency and selectivity to cancer cells over normal cells.

  DOI：

  10.1021/co1000234
• 作为产物：
  描述：

  2-thiocyanato-1-(thiophen-2-yl)ethan-1-one 在 氢溴酸 、 溶剂黄146 作用下， 以 水 为溶剂， 生成 2-溴-4-(2-噻吩基)噻唑
  参考文献：
  名称：

  One-Pot Tandem Copper-Catalyzed Library Synthesis of 1-Thiazolyl-1,2,3-triazoles as Anticancer Agents

  摘要：

  One-pot multicomponent synthesis to assemble compounds has been an efficient method for constructing a compound library. We have developed one-pot tandem copper-catalyzed azidation and CuAAC reactions that afford 1-thiazolyl-1,2,3-triazoles with anticancer activity. By utilizing this one-pot synthetic strategy, we constructed a library of 1-thiazolyl-1,2,3-triazoles in search of the potent lead compound. Furthermore, 1-thiazolyl-1,2,3-triazoles were evaluated for anticancer activity against the multidrug-resistant cancer cells MES-SA/Dx5. Most of the 1-thiazolyl-1,2,3-triazoles revealed cytotoxic effect against cancer cells at micromolar to low micromolar range. Testing some of the most potent compounds (5{4,2-4} and 5{5,1-3}) against the normal cell line Vero showed no significant toxicity (except 5{4,2}) to normal cells. This result indicates that compounds 5{4,3-4} and 5{5,1-3} possessed good potency and selectivity to cancer cells over normal cells.

  DOI：

  10.1021/co1000234