1-(4-phenylthiazol-2-yl)-4-(thiophen-2-yl)-1H-1,2,3-triazole | 1258795-47-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(4-phenylthiazol-2-yl)-4-(thiophen-2-yl)-1H-1,2,3-triazole
• 英文别名: 4-Phenyl-2-(4-thiophen-2-yltriazol-1-yl)-1,3-thiazole
• CAS: 1258795-47-9
• 化学式: C₁₅H₁₀N₄S₂
• 分子量: 310.403
• InChiKey: AUIITPCKHMENQC-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  100
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  苯乙酰基硫氰酸酯 在 copper(l) iodide 、 sodium azide 、 氢溴酸 、 溶剂黄146 、 N,N'-二甲基乙二胺 作用下， 以 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 6.0h， 生成 1-(4-phenylthiazol-2-yl)-4-(thiophen-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