5-amino-3,6-dihydro-3-<(2-hydroxyethoxy)methyl>-7H-1,2,3-triazolo<4,5-d>pyrimidin-7-one | 81475-46-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 三唑并嘧啶类
• 英文名称: 5-amino-3,6-dihydro-3-<(2-hydroxyethoxy)methyl>-7H-1,2,3-triazolo<4,5-d>pyrimidin-7-one
• 英文别名: 9-(2-hydroxyethoxymethyl)-8-azaguanine；5-amino-3-(2-hydroxyethoxymethyl)-6H-triazolo[4,5-d]pyrimidin-7-one
• CAS: 81475-46-9
• 化学式: C₇H₁₀N₆O₃
• 分子量: 226.195
• InChiKey: NYYGMQYRBASACQ-UHFFFAOYSA-N

物化性质

• 密度：
  1.95±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  128
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  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

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。
• Anti-viral guanine derivatives
  申请人：Merck & Co., Inc.

  公开号：EP0074306A2

  公开（公告）日：1983-03-16

  9-(1,3-dihydroxy-2-propoxymethyl)guanine and 9-(2,3-dihydroxy-1-propoxymethyl)guanine have been found to have potent anti-viral activity against herpes viruses. These compounds, their acyl derivatives, their phosphate derivatives and their pharmaceutically acceptable salts, pharmaceutical formulations containing these compounds, the treatment of viral infections with these compounds, methods of preparing these compounds, and novel intermediates useful in their preparation are all disclosed. The compounds may be prepared by reaction of the appropriate acetoxymethyl ether with diacetylguanine, followed by deprotection. The acetoxymethyl ethers may be obtained by reaction of glycerol formal with acetic anhydride in the presence of a catalyst.

  已发现 9-(1,3-二羟基-2-丙氧基甲基)鸟嘌呤和 9-(2,3-二羟基-1-丙氧基甲基)鸟嘌呤对疱疹病毒具有很强的抗病毒活性。 现已公开这些化合物、其酰基衍生物、其磷酸盐衍生物及其药学上可接受的盐、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。 这些化合物可通过适当的乙酰氧甲基醚与二乙酰鸟嘌呤反应，然后进行脱保护来制备。 乙酰氧甲基醚可通过甘油甲醛与乙酸酐在催化剂存在下反应来获得。
• Anti-viral compounds, their preparation and anti-viral compositions
  申请人：Merck & Co., Inc.

  公开号：EP0165164A1

  公开（公告）日：1985-12-18

  9-(1, 3-Dihydroxy-2-propoxymethyl) quanine and 9-(2, 3-dihydroxy-1-propoxymethyl) guanine have been found to have potent anti-viral activity against herpes viruses. These compounds, their acyl derivatieves, their phosphate derivatives and their pharmaceutically acceptable salts, phar-- maceutical formulations containing these compounds, the treatment of DNA viral or herpes viral infections with these compounds, methods of preparing these compounds, and novel intermediates useful in their preparation are all disclosed. The compounds may be prepared by reaction of the appropriate acetoxymethyl ether with diacetyl-quanine, followed by deprotection. The acetoxymethyl ethers may be obtained by reaction of glycerol formal with acetic anhydride in the presence of a catalyst.

  9-(1,3-二羟基-2-丙氧基甲基)鸟嘌呤和9-(2,3-二羟基-1-丙氧基甲基)鸟嘌呤已被发现对疱疹病毒具有很强的抗病毒活性。 本文公开了这些化合物、它们的酰基衍生物、它们的磷酸衍生物和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病毒或疱疹病毒感染、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。 这些化合物可以通过适当的乙酰氧甲基醚与二乙酰基鸟嘌呤反应，然后进行脱保护来制备。 乙酰氧甲基醚可以通过甘油醛与乙酸酐在催化剂存在下反应来获得。
• 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。
• 9(2-(hydroxymethyl) cycloalkylmethyl)guanines
  申请人：Merck & Co., Inc.

  公开号：EP0291229A2

  公开（公告）日：1988-11-17

  9-[2-(Hydroxymethyl)cycloalkylmethyl]guanines which are herpes simplex viral thymidine kinase inhibitors, their acyl derivatives, their phosphate 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.

  9-[2-(羟甲基)环烷基甲基]鸟嘌呤是单纯疱疹病毒胸苷激酶抑制剂、它们的酰基衍生物、它们的磷酸衍生物和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。