5-amino-1--1,2,4-triazole | 21796-00-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 英文名称: 5-amino-1--1,2,4-triazole
• 英文别名: 5-amino-[1,2,4]triazole-1-carbothioic acid anilide；1-Anilinothioformyl-5-amino-1,2,4-triazol；1-(Anilinothioformyl)-5-amino-1,2,4-triazole；5-amino-N-phenyl-1,2,4-triazole-1-carbothioamide
• CAS: 21796-00-9
• 化学式: C₉H₉N₅S
• 分子量: 219.27
• InChiKey: HPNAWNSQLIMXMU-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  15
• 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：
  101
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  5-amino-1--1,2,4-triazole 反应 0.67h， 以88%的产率得到N,N'-bis(1,2,4-triazol-3-yl)thiourea
  参考文献：
  名称：

  Synthesis and uncoupling activities of hydrophobic thioureas.

  摘要：

  制备并测试了各种N-芳基-N'-苯基硫脲、N,N'-二芳基硫脲和N-(1,2,4-三唑-3-基)-N'-芳基硫脲的解偶联活性。结果表明，对于解偶联活性而言，二芳基硫脲的苯基4-位取代非常重要。含有两个或更多卤素原子的二苯基硫脲表现出强烈的活性。在两个苯基上都含有硝基的化合物显示出最高的活性。这些结果表明，化合物对疏水性和酸性对于解偶联活性具有首要重要性。当硫脲被吡啶和1,2,4-三唑环取代时，活性显著下降。还研究了苯基异硫氰酸酯与3-氨基-1,2,4-三唑的反应。

  DOI：

  10.1248/cpb.33.662
• 作为产物：
  描述：

  3-氨基-1,2,4-三氮唑 、 硫代异氰酸苯酯 以 N,N-二甲基甲酰胺 为溶剂， 反应 60.0h， 以2.7%的产率得到5-amino-1--1,2,4-triazole
  参考文献：
  名称：

  Synthesis and Pharmacological Activity of Triazole Derivatives Inhibiting Eosinophilia

  摘要：

  In order to develop novel antiasthmatic agents based on a new mechanism of action, a series of 3-substituted 5-amino-1-[(methylamino)(thiocarbonyl)]-1H-1,2,4-triazole derivatives were synthesized and evaluated in a model in which eosinophilia was induced in the ah-way through intravenous (iv) injection of Sephadex particles on days 0, 2, and 5. After screening of several hundred derivatives, we finally identified the highly potent eosinophilia inhibitor 5-amino-3-(4-chlorophenyl)-1-[(methylamino)(thiocarbonyl)]-1H-triazole (23c, GCC-AP0341), which had ID50 values of 0.3 and 0.07 mg/kg when administered orally (os) and intraperitoneally tip), respectively. This compound showed complete inhibition of the hypersensitivity induced by ascaris inhalation at an ip dose of 1 mg/kg as well as low toxicity, with an LD(50) value of > 2.0 g/kg in mice. Extensive study of its mechanism of action revealed that 23c inhibited eosinophil survival induced by interleukin-5 (IL-5), but had little or no effect on leukotriene D-4 (LTD(4)) or platelet-activating factor (PAF)-induced responses. Taken together, these results suggest 23e as a novel candidate for the treatment of chronic asthma. Further studies are now underway.

  DOI：

  10.1021/jm9507993