4-chloro-8-methyl[1,2,4]triazolo[4,3-a]quinoxaline-1-amine | 1337569-14-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氮杂萘
• 英文名称: 4-chloro-8-methyl[1,2,4]triazolo[4,3-a]quinoxaline-1-amine
• 英文别名: 4-chloro-8-methyl-[1,2,4]triazolo[4,3-a]quinoxalin-1-amine
• CAS: 1337569-14-8
• 化学式: C₁₀H₈ClN₅
• 分子量: 233.66
• InChiKey: KDADEAIJRAFWDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.5
• 重原子数：
  16
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.1
• 拓扑面积：
  69.1
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-chloro-8-methyl[1,2,4]triazolo[4,3-a]quinoxaline-1-amine 在 吡啶 、 三乙胺 作用下， 以 5,5-dimethyl-1,3-cyclohexadiene 为溶剂， 反应 24.5h， 生成 N-[8-methyl-4-(4-o-tolylpiperazin-1-yl)[1,2,4]triazolo[4,3-a]quinoxalin-1-yl]benzamide
  参考文献：
  名称：

  [1,2,4]Triazolo[4,3-a]quinoxaline: synthesis, antiviral, and antimicrobial activities

  摘要：

  A series of novel [1,2,4]triazolo[4,3-a]quinoxaline derivatives and their isosteres, pyrimido-quinoxaline, were synthesized as potential antiviral and antimicrobial agents. The new compounds were synthesized via aromatic nucleophilic substitution of 4-chloro-8-methyl[1,2,4]triazolo[4,3-a]quinoxaline-1-amine with different amines and triazole-2-thiol. Some of the synthesized compounds were subjected to antiviral and cytotoxicity screening using plaque-reduction assay. Most of the tested compounds exhibited cytotoxicity at concentration 160 mu g/ml and compound 8b showed promising antiviral activity. In vitro antimicrobial screening against different pathogenic organisms using agar diffusion method demonstrated that compounds 4d, 6c, 7b, and 8a exhibit antibacterial and/or antifungal activities.

  DOI：

  10.1007/s00044-011-9753-7
• 作为产物：
  描述：

  2,3-二氯-6-甲基喹喔啉 、 氨基硫脲 以 正丁醇 为溶剂， 反应 6.0h， 以75%的产率得到4-chloro-8-methyl[1,2,4]triazolo[4,3-a]quinoxaline-1-amine
  参考文献：
  名称：

  [1,2,4]Triazolo[4,3-a]quinoxaline: synthesis, antiviral, and antimicrobial activities

  摘要：

  A series of novel [1,2,4]triazolo[4,3-a]quinoxaline derivatives and their isosteres, pyrimido-quinoxaline, were synthesized as potential antiviral and antimicrobial agents. The new compounds were synthesized via aromatic nucleophilic substitution of 4-chloro-8-methyl[1,2,4]triazolo[4,3-a]quinoxaline-1-amine with different amines and triazole-2-thiol. Some of the synthesized compounds were subjected to antiviral and cytotoxicity screening using plaque-reduction assay. Most of the tested compounds exhibited cytotoxicity at concentration 160 mu g/ml and compound 8b showed promising antiviral activity. In vitro antimicrobial screening against different pathogenic organisms using agar diffusion method demonstrated that compounds 4d, 6c, 7b, and 8a exhibit antibacterial and/or antifungal activities.

  DOI：

  10.1007/s00044-011-9753-7