2-((5-氨基甲酰基-1H-1,2,4-三唑-1-基)甲氧基)乙酸乙酯 | 96445-89-5

• 分子结构分类: 有机化合物
• 中文名称: 2-((5-氨基甲酰基-1H-1,2,4-三唑-1-基)甲氧基)乙酸乙酯
• 英文名称: 2-<(5-carbamoyl-1H-1,2,4-triazol-1-yl)methoxy>ethyl acetate
• 英文别名: 2-[(5-carbamoyl-1,2,4-triazol-1-yl)methoxy]ethyl acetate
• CAS: 96445-89-5
• 化学式: C₈H₁₂N₄O₄
• 分子量: 228.208
• InChiKey: UWBSXQFZSJXGTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  445.4±51.0 °C(Predicted)
• 密度：
  1.45±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.09
• 重原子数：
  16.0
• 可旋转键数：
  6.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  109.33
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-((5-氨基甲酰基-1H-1,2,4-三唑-1-基)甲氧基)乙酸乙酯 在 ammonium hydroxide 作用下， 反应 1.0h， 生成 1-(2-羟基乙氧基甲基)-1,2,4-三唑-5-甲酰胺
  参考文献：
  名称：

  Modifications on the heterocyclic base of acyclovir: syntheses and antiviral properties

  摘要：

  A group of compounds was prepared in which variations of the ring portion of the acyclovir (ACV) structure were made. These modifications included monocyclic (isocytosine, triazole, imidazole), bicyclic (8-azapurine, pyrrolo[2,3-d]pyrimidine, pyrazolo[3,4-d]pyrimidine) and tricyclic (linear benzoguanine) congeners. The derivatives were evaluated against herpes simplex virus type 1 (HSV-1) by the plaque-inhibition and plaque-reduction methods with only the 8-azapurine analogue 28 showing some activity. In a test measuring the ability of these compounds to inhibit the HSV-1 thymidine kinase, 28 and the tricyclic derivative 38 exhibited competition with ACV for binding to the enzyme. The inability of the group to exert significant antiherpetic action is attributed to their lack of phosphorylation to the requisite triphosphate stage.

  DOI：

  10.1021/jm00146a002
• 作为产物：
  描述：

  阿昔洛韦侧链 、 3-氰基-1,2,4-三氮唑 在 双(对硝基苯基)磷酸酯 作用下， 反应 0.4h， 以68%的产率得到2-<(3-cyano-1H-1,2,4-triazol-1-yl)methoxy>ethyul acetate
  参考文献：
  名称：

  Modifications on the heterocyclic base of acyclovir: syntheses and antiviral properties

  摘要：

  A group of compounds was prepared in which variations of the ring portion of the acyclovir (ACV) structure were made. These modifications included monocyclic (isocytosine, triazole, imidazole), bicyclic (8-azapurine, pyrrolo[2,3-d]pyrimidine, pyrazolo[3,4-d]pyrimidine) and tricyclic (linear benzoguanine) congeners. The derivatives were evaluated against herpes simplex virus type 1 (HSV-1) by the plaque-inhibition and plaque-reduction methods with only the 8-azapurine analogue 28 showing some activity. In a test measuring the ability of these compounds to inhibit the HSV-1 thymidine kinase, 28 and the tricyclic derivative 38 exhibited competition with ACV for binding to the enzyme. The inability of the group to exert significant antiherpetic action is attributed to their lack of phosphorylation to the requisite triphosphate stage.

  DOI：

  10.1021/jm00146a002