2-((2-氨基-1,4-二氢-4-氧代-1-嘧啶基)甲氧基)苯甲酸乙酯 | 96445-92-0

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯和取代衍生物
• 中文名称: 2-((2-氨基-1,4-二氢-4-氧代-1-嘧啶基)甲氧基)苯甲酸乙酯
• 英文名称: 2-<(2-amino-1,4-dihydro-4-oxo-1-pyrimidinyl)methoxy>ethyl benzoate
• 英文别名: 2-[(2-amino-4-oxopyrimidin-1-yl)methoxy]ethyl benzoate
• CAS: 96445-92-0
• 化学式: C₁₄H₁₅N₃O₄
• 分子量: 289.291
• InChiKey: FDMYSUNOZIRMMW-UHFFFAOYSA-N

物化性质

• 沸点：
  434.0±51.0 °C(Predicted)
• 密度：
  1.30±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.66
• 重原子数：
  21.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  96.44
• 氢给体数：
  1.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  2-((2-氨基-1,4-二氢-4-氧代-1-嘧啶基)甲氧基)苯甲酸乙酯 在 甲胺 作用下， 以72%的产率得到1-<(2-hydroxyethoxy)methyl>-2-aminopyrimidin-4-one
  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：

  乙二醇单苯并酸酯 在 盐酸 、 sodium hydride 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 21.5h， 生成 2-((2-氨基-1,4-二氢-4-氧代-1-嘧啶基)甲氧基)苯甲酸乙酯
  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