2-<(5-amino-6,7-dihydro-7-oxo-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)methoxy>ethyl benzoate | 96445-98-6

• 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: 2-<(5-amino-6,7-dihydro-7-oxo-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)methoxy>ethyl benzoate
• 英文别名: 9-(2-benzoyloxyethoxymethyl)-8-azaguanine；2-[(5-amino-7-oxo-6H-triazolo[4,5-d]pyrimidin-3-yl)methoxy]ethyl benzoate
• CAS: 96445-98-6
• 化学式: C₁₄H₁₄N₆O₄
• 分子量: 330.303
• InChiKey: RGSNFNBVCIRDPG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0
• 重原子数：
  24
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  134
• 氢给体数：
  2
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-<(5-amino-6,7-dihydro-7-oxo-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)methoxy>ethyl benzoate 在 甲胺 作用下， 反应 30.0h， 以80%的产率得到5-amino-3,6-dihydro-3-<(2-hydroxyethoxy)methyl>-7H-1,2,3-triazolo<4,5-d>pyrimidin-7-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 作用下， 以 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 147.0h， 生成 2-<(5-amino-6,7-dihydro-7-oxo-3H-1,2,3-triazolo<4,5-d>pyrimidin-3-yl)methoxy>ethyl benzoate
  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

• 8-Azapurine derivatives
  申请人：Burroughs Wellcome Co.

  公开号：US04027025A1

  公开（公告）日：1977-05-31

  9-Hydroxyethoxymethyl (and related) derivatives of 2-amino-6-substituted-8-azapurines have been found to have potent anti-viral activities. Novel compounds and their pharmaceutically acceptable salts, pharmaceutical formulations containing the compounds of this invention, and the treatment of viral infections with these formulations are all disclosed. 9-(2-Hydroxyethoxymethyl)-8-azaguanine and 9-(2-benzoyloxyethoxymethyl)-8-azaguanine are examples of active compounds of this invention.

  2-氨基-6-取代-8-氮杂嘌呤的9-羟乙氧甲基（及相关）衍生物被发现具有强效的抗病毒活性。本发明揭示了新化合物及其药用可接受的盐、含有本发明化合物的药物配方以及使用这些配方治疗病毒感染。9-(2-羟乙氧甲基)-8-氮嘌呤和9-(2-苯甲酰氧乙氧甲基)-8-氮嘌呤是本发明的活性化合物的示例。
• 1-(2-(Hydroxymethyl)-cycloalkylmethyl)-5-substituted uracils
  申请人：Merck & Co., Inc.

  公开号：EP0291230A2

  公开（公告）日：1988-11-17

  1-[2-(Hydroxymethyl)cycloalkylmethyl]-5-­substituted uracils which are herpes simplex viral thymidine kinase inhibitors, their acyl derivatives, and their pharmaceutically-acceptable salts; pharmaceutical formulations containing these compounds; the treatment of DNA viral, particularly herpes viral, infections with these compounds; methods of preparing these compounds; and novel intermediates useful in their preparation.

  1-[2-（羟甲基）环烷基甲基]-5-取代的尿嘧啶，它是单纯疱疹病毒胸苷激酶抑制剂，它们的酰基衍生物，以及它们的药学上可接受的盐；含有这些化合物的药物制剂；用这些化合物治疗 DNA 病毒感染，特别是疱疹病毒感染；制备这些化合物的方法；以及用于制备这些化合物的新型中间体。
• Anti-viral guanine derivatives
  申请人：Merck & Co., Inc.

  公开号：EP0074306B1

  公开（公告）日：1988-06-01
• 9(2-(hydroxymethyl) cycloalkylmethyl)guanines
  申请人：Merck & Co., Inc.

  公开号：EP0291229B1

  公开（公告）日：1994-04-13
• US4027025A
  申请人：——

  公开号：US4027025A

  公开（公告）日：1977-05-31