6-氨基-1-(2-甲氧基-乙基)-1H-嘧啶-2,4-二酮 | 56075-76-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 中文名称: 6-氨基-1-(2-甲氧基-乙基)-1H-嘧啶-2,4-二酮
• 英文名称: 6-amino-1-(2-methoxyethyl)-1,3-dihydropyrimidine-2,4-dione
• 英文别名: 1-(2-methoxyethyl)-6-aminouracil；6-amino-1-(2-methoxyethyl)pyrimidine-2,4(1H,3H)-dione；6-amino-1-(2-methoxyethyl)pyrimidine-2,4-dione
• CAS: 56075-76-4
• 化学式: C₇H₁₁N₃O₃
• mdl: MFCD03954446
• 分子量: 185.183
• InChiKey: YZEWEIJSLLACIN-UHFFFAOYSA-N

物化性质

• 熔点：
  236-238 °C
• 密度：
  1.269±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.4
• 重原子数：
  13
• 可旋转键数：
  3
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.428
• 拓扑面积：
  84.7
• 氢给体数：
  2
• 氢受体数：
  4

安全信息

• 海关编码：
  2933599090

反应信息

• 作为反应物：
  描述：

  6-氨基-1-(2-甲氧基-乙基)-1H-嘧啶-2,4-二酮 在 碘代三甲硅烷 、 4-己基苯胺 作用下， 以 氯仿 为溶剂， 反应 4.67h， 生成 1-(2-hydroxyethyl)-6-(4-hexylanilino)uracil
  参考文献：
  名称：

  Molecular Modeling and Synthesis of Inhibitors of Herpes Simplex Virus Type 1 Uracil-DNA Glycosylase

  摘要：

  We recently reported the properties of the first selective inhibitors of herpes simplex virus type 1 (HSV1) uracil-DNA glycosylase (UDG), an enzyme of DNA repair that has been proposed to be required for reactivation of the virus from latency. 6-(4-Octylanilino)uracil (octAU) was the most potent inhibitor among a series of 6-(4-alkylanilino)uracils, acting in the micromolar range and without effect against human UDG. A 28.5-kDa catalytic fragment of HSV1 UDG has been crystallized in the presence of uracil, and the structure was recently solved. We have used the coordinates of this structure in order to study interaction of our inhibitors with the enzyme, and a model of binding between octAU and UDG has been derived. Starting with the optimized model, the activity of several octAU analogues was predicted, and the values compared favorably with experimental results found for the synthetic compounds. Several hydrophilic derivatives were predicted and found to be active as UDG inhibitors. These compounds will be useful to determine if UDG, like the viral thymidine kinase, is required for reactivation of HSV1 from latency in nerve cells.

  DOI：

  10.1021/jm980718d
• 作为产物：
  描述：

  N-(2-甲氧基乙基)脲 、 氰乙酸乙酯 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 6.0h， 以82%的产率得到6-氨基-1-(2-甲氧基-乙基)-1H-嘧啶-2,4-二酮
  参考文献：
  名称：

  Molecular Modeling and Synthesis of Inhibitors of Herpes Simplex Virus Type 1 Uracil-DNA Glycosylase

  摘要：

  We recently reported the properties of the first selective inhibitors of herpes simplex virus type 1 (HSV1) uracil-DNA glycosylase (UDG), an enzyme of DNA repair that has been proposed to be required for reactivation of the virus from latency. 6-(4-Octylanilino)uracil (octAU) was the most potent inhibitor among a series of 6-(4-alkylanilino)uracils, acting in the micromolar range and without effect against human UDG. A 28.5-kDa catalytic fragment of HSV1 UDG has been crystallized in the presence of uracil, and the structure was recently solved. We have used the coordinates of this structure in order to study interaction of our inhibitors with the enzyme, and a model of binding between octAU and UDG has been derived. Starting with the optimized model, the activity of several octAU analogues was predicted, and the values compared favorably with experimental results found for the synthetic compounds. Several hydrophilic derivatives were predicted and found to be active as UDG inhibitors. These compounds will be useful to determine if UDG, like the viral thymidine kinase, is required for reactivation of HSV1 from latency in nerve cells.

  DOI：

  10.1021/jm980718d

文献信息

• A2B adenosine receptor antagonists
  申请人：Kalla Rao

  公开号：US20050101778A1

  公开（公告）日：2005-05-12

  Disclosed are novel A 2B adenosine receptor antagonists having the structure of Formula I or Formula II: The compounds are particularly useful for treating asthma, inflammatory gastrointestinal tract disorders, cardiovascular diseases, neurological disorders, and diseases related to undesirable angiogenesis.

  揭示了具有Formula I或Formula II结构的新型A2B腺苷受体拮抗剂：这些化合物特别适用于治疗哮喘、炎症性胃肠道疾病、心血管疾病、神经系统疾病以及与不良血管生成相关的疾病。
• A2B Adenosine receptor antagonists
  申请人：Kalla Rao

  公开号：US20050261316A1

  公开（公告）日：2005-11-24

  Disclosed are novel compounds that are A 2B adenosine receptor antagonists, useful for treating various disease states, including asthma and diarrhea.

  揭示了一种新颖的化合物，它们是A2B腺苷受体拮抗剂，可用于治疗包括哮喘和腹泻在内的各种疾病状态。
• Recyclization Reactions of 5-Formyl-1,3-dimethyluracil with Electron-Rich Amino Heterocycles
  作者：Dmitriy Volochnyuk、Alexander Shivanyuk、Andrey Mityuk、Sergey Ryabukhin、Andrey Plaskon、Andrey Tolmachev

  DOI：10.1055/s-0029-1216798

  日期：2009.6

  Recyclization reactions of 5-formyl-1,3-dimethyluracil with various electron-rich five- or six-membered amino heterocycles led to the formation of a series of fused heterocycles containing a nicotinic acid unit. 5-formyl-1,3-dimethyluracil - amino heterocycles - fused pyridines - fused-ring systems - recyclization reactions

  5-甲酰基-1,3-二甲基尿嘧啶与各种富电子的五元或六元氨基杂环的环化反应导致形成一系列包含烟酸单元的稠合杂环。 5-甲酰基-1,3-二甲基尿嘧啶-氨基杂环-稠合吡啶-稠环系统-再循环反应
• Novel Nonsubstrate Inhibitors of Human Thymidine Phosphorylase, a Potential Target for Tumor-Dependent Angiogenesis
  作者：Federico Focher、Daniela Ubiali、Massimo Pregnolato、Chengxin Zhi、Joseph Gambino、George E. Wright、Silvio Spadari

  DOI：10.1021/jm000037u

  日期：2000.6.1

  is an enzyme involved in thymidine metabolism and homeostasis, and its catalytic activity appears to play an important role in angiogenesis. Here we describe the cloning and expression of a His-tagged human TP/PD-ECGF and its assay with uracil and thymine analogues. We present the design, synthesis, and biological evaluation of novel 6-(phenylalkylamino)uracil derivatives which, at micromolar concentrations

  胸苷磷酸化酶/血小板源性内皮细胞生长因子（TP / PD-ECGF）是一种参与胸苷代谢和体内稳态的酶，其催化活性似乎在血管生成中起重要作用。在这里，我们描述了带有组氨酸标签的人TP / PD-ECGF的克隆和表达及其尿嘧啶和胸腺嘧啶类似物的测定。我们目前的设计，合成和新型的6-（苯基烷基氨基）尿嘧啶衍生物的生物评估，在微摩尔浓度，抑制人TP的分解代谢和合成代谢反应。这些碱基类似物不会被酶转化为核苷形式，因此代表了该酶的纯非底物抑制剂。
• A2B ADENOSINE RECEPTOR ANTAGONISTS
  申请人：Kalla Rao

  公开号：US20080318983A1

  公开（公告）日：2008-12-25

  Disclosed are methods for treating asthma, inflammatory gastrointestinal tract disorders, cancer, cardiovascular diseases, neurological disorders, and diseases related to undesirable angiogenesis using A 2B adenosine receptor antagonists having the structure of Formula I or Formula II:

  本发明涉及使用具有结构公式I或公式II的A2B腺苷受体拮抗剂治疗哮喘、炎症性肠道疾病、癌症、心血管疾病、神经系统疾病和与不良血管生成有关的疾病的方法。