4-(4-((4-formyl-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide | 1456736-86-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 4-(4-((4-formyl-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide
• 英文别名: 4-[4-[(4-formyl-2-methoxyphenoxy)methyl]triazol-1-yl]-N-(2-phenylethyl)benzenesulfonamide
• CAS: 1456736-86-9
• 化学式: C₂₅H₂₄N₄O₅S
• 分子量: 492.555
• InChiKey: XGFLUNMXMLDPFI-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  35
• 可旋转键数：
  11
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.16
• 拓扑面积：
  121
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  4-氨基-N-(2-苯基乙基)苯磺酰胺 在 盐酸 、 Vitamin C 、 copper(II) sulfate pentahydrate 、 溶剂黄146 、 sodium nitrite 作用下， 以 水 、 叔丁醇 为溶剂， 反应 2.75h， 生成 4-(4-((4-formyl-2-methoxyphenoxy)methyl)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide
  参考文献：
  名称：

  Synthesis and cytotoxicity of novel 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamides

  摘要：

  A new series of 4-(4-(substituted)-1H-1,2,3-triazol-1-yl)-N-phenethylbenzenesulfonamide derivatives 5 were synthesized through the Click approach and evaluated for their cytotoxic activity against four cancer cell lines (HuCCA-1, HepG2, A549, and MOLT-3). Most of the synthesized triazoles 5 displayed cytotoxicity against MOLT-3 cell line, except for analogs 5a-c and 5e. Significantly, 4-phenyltriazoles (5a and 5n), 4-(naphthalen-2-yloxy)methyltriazole 5d, as well as 4-((2-oxo-2H-chromen-7-yl)oxy)methyltriazole 5l showed higher cytotoxic activity against HepG2 cells than the reference drug, etoposide. Interestingly, the 4-phenyltriazole 5a was the most potent and promising compound with IC50 value of 9.07 mu M against HepG2 cell line. The analog 5a also exerted the highest cytotoxic activity against HuCCA-1 cells. This finding provides the novel lead molecules for further development.

  DOI：

  10.1007/s00044-013-0777-z