6-amino-3,7-dihydro-3-<(2-hydroxyethoxy)-methyl>-8H-imidazo<4,5-g>quinazolin-8-one | 96446-05-8

• 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: 6-amino-3,7-dihydro-3-<(2-hydroxyethoxy)-methyl>-8H-imidazo<4,5-g>quinazolin-8-one
• 英文别名: 6-amino-3-(2-hydroxyethoxymethyl)-7H-imidazo[4,5-g]quinazolin-8-one
• CAS: 96446-05-8
• 化学式: C₁₂H₁₃N₅O₃
• 分子量: 275.267
• InChiKey: SFAFFMWDFHPZIL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  115
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  lin-benzoguanine 在 硫酸氢铵 、 三乙胺 、 甲胺 作用下， 以 甲苯 为溶剂， 反应 22.08h， 生成 6-amino-3,7-dihydro-3-<(2-hydroxyethoxy)-methyl>-8H-imidazo<4,5-g>quinazolin-8-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

文献信息

• Modifications on the heterocyclic base of acyclovir: syntheses and antiviral properties
  作者：Lilia M. Beauchamp、Bart L. Dolmatch、Howard J. Schaeffer、Peter Collins、D. J. Bauer、Paul M. Keller、James A. Fyfe

  DOI：10.1021/jm00146a002

  日期：1985.8

  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.