1-<(2-hydroxyethoxy)methyl>-2-aminopyrimidin-4-one | 91897-92-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: 1-<(2-hydroxyethoxy)methyl>-2-aminopyrimidin-4-one
• 英文别名: 2-amino-1-<(2-hydroxyethoxy)methyl>-4(1H)-pyrimidinone；2-amino-1-((2-hydroxyethoxy)methyl)pyrimidine-4(1H)-one；1-((2-Hydroxethoxy)methyl)-isocytosine；2-amino-1-(2-hydroxyethoxymethyl)pyrimidin-4-one
• CAS: 91897-92-6
• 化学式: C₇H₁₁N₃O₃
• 分子量: 185.183
• InChiKey: GELNYZOACSQCRO-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.9
• 重原子数：
  13
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.43
• 拓扑面积：
  88.2
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  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

文献信息

• Nucleic acid related compounds. 47. Synthesis and biological activities of pyrimidine and purine "acyclic" nucleoside analogs
  作者：Morris J. Robins、Peter W. Hatfield、Jan Balzarini、Erik De Clercq

  DOI：10.1021/jm00377a018

  日期：1984.11

  Various acyclic, i.e., (2-hydroxyethoxy)methyl and (2-acetoxyethoxy)methyl, analogues of pyrimidine and purine nucleosides have been prepared and evaluated for their antiviral, antimetabolic, and cytotoxic properties. All of the pyrimidine analogues, including (E)-5-(2-bromovinyl)-1-[(2-hydroxyethoxy)methyl]uracil (12) and its O-acetyl derivative (13), were virtually devoid of antiviral, cytotoxic

  已经制备了嘧啶和嘌呤核苷的各种无环的，即（2-羟基乙氧基）甲基和（2-乙酰氧基乙氧基）甲基类似物，并评估了它们的抗病毒，抗代谢和细胞毒性特性。所有嘧啶类似物，包括（E）-5-（2-溴乙烯基）-1-[（2-羟基乙氧基）甲基]尿嘧啶（12）及其O-乙酰基衍生物（13），都几乎没有抗病毒，细胞毒性以及抗代谢活动。但是，几种9-[（（2-羟基乙氧基）甲基]鸟嘌呤（acyclovir）的8取代衍生物在体外具有比母体药物更高的抗病毒特异性。8-甲基-，8-氨基-，8-溴-和8-碘代阿昔洛韦衍生物具有值得进一步研究的活性。