3-(4'-trifluoromethylphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole | 1284312-38-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 3-(4'-trifluoromethylphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole
• 英文别名: 1-methyl-3-[3-[4-(trifluoromethyl)phenyl]-1H-1,2,4-triazol-5-yl]indole
• CAS: 1284312-38-4
• 化学式: C₁₈H₁₃F₃N₄
• 分子量: 342.323
• InChiKey: BEUKDQCERFIXFZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.3
• 重原子数：
  25
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.11
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  3-吲哚甲醛 在 甲酸 、 盐酸羟胺 、 sodium formate 、 potassium carbonate 作用下， 以 N,N-二甲基甲酰胺 、 正丁醇 为溶剂， 反应 11.0h， 生成 3-(4'-trifluoromethylphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole
  参考文献：
  名称：

  Synthesis of Novel Indolyl-1,2,4-triazoles as Potent and Selective Anticancer Agents

  摘要：

  A diverse series of 22 indolyl-1,2,4-triazole congeners (6 and 7) have been synthesized from the reaction of indole-3-carbonitrile (4) or (5) with appropriate acid hydrazides in the presence of potassium carbonate. Synthesized compounds were evaluated for their cytotoxicity against six human cancer cell lines, and some of the compounds displayed promising activity. In particular, 3-(3',4',5'-trimethoxyphenyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7i) and 3-(4'-piperidinyl)-5-(N-methyl-3'-indolyl)-1,2,4-triazole (7n) were the most promising and broadly active compounds against the tested cell lines. It was interesting to note that the trimethoxyphenyl analog 7i showed twofold selective cytotoxicity against PaCa2 cell line (IC50 0.8 mu m), whereas piperidinyl analog 7n was found to be selectively cytotoxic against MCF7 cell line (IC50 1.6 mu m). Notably, the 4-fluorophenyl derivative 7c exhibited selective cytotoxicity against PC3 cell line (IC50 4 mu m). The structure-activity relationship study revealed that substituents including 3,4,5-trimethoxyphenyl, 3,4-dimethoxyphenyl, 4-benzyloxy-3-methoxyphenyl, 4-piperidinyl, 4-fluorophenyl and N-methylindole are beneficial for the activity of indolyl-1,2,4-triazoles (6 and 7).

  DOI：

  10.1111/j.1747-0285.2010.01051.x