1,3-二(羟基甲基)嘧啶-2,4-二酮 | 79719-29-2

• 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: 1,3-二(羟基甲基)嘧啶-2,4-二酮
• 英文名称: 1,3-dihydroxymethyluracil
• 英文别名: 1,3-bishydroxymethyl uracil；2,4(1H,3H)-Pyrimidinedione, 1,3-bis(hydroxymethyl)-；1,3-bis(hydroxymethyl)pyrimidine-2,4-dione
• CAS: 79719-29-2
• 化学式: C₆H₈N₂O₄
• 分子量: 172.141
• InChiKey: XVTXBNKTGQKGLQ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.2
• 重原子数：
  12
• 可旋转键数：
  2
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.33
• 拓扑面积：
  81.1
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  4-碘苯甲酸 、 1,3-二(羟基甲基)嘧啶-2,4-二酮 在 4-二甲氨基吡啶 、 N,N'-二环己基碳二亚胺 作用下， 生成 (2,4-Dioxopyrimidin-1-yl)methyl 4-iodobenzoate
  参考文献：
  名称：

  The design and synthesis of ALS inhibitors from pharmacophore models

  摘要：

  In search of new ALS inhibitors without the previous knowledge of receptor crystal structure, DISCO module was applied to produce 3D-pharmacophore models, which provided information to design novel molecules by 3D-database searching. Then a number of molecules were synthesized. Several of them have some ALS inhibitory activities. (C) 1999 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0960-894x(99)00301-7
• 作为产物：
  描述：

  聚合甲醛 、 尿嘧啶 在 pH 5 作用下， 以 水 为溶剂， 生成 1,3-二(羟基甲基)嘧啶-2,4-二酮
  参考文献：
  名称：

  氮杂环的N-羟甲基衍生物作为可能的前药I：尿嘧啶的N-羟甲基化。

  摘要：

  制备了1，3-二羟甲基尿嘧啶，3-羟甲基-1-甲基尿嘧啶和1-羟甲基-3-甲基尿嘧啶的固体样品，并通过光谱分析确认了它们的结构。还研究了在甲醛水溶液中形成N-羟甲基化尿嘧啶的热力学和动力学。用于形成N-1-羟甲基衍生物的平衡常数大约是用于形成N-3-羟甲基衍生物的平衡常数的两倍，并且它们在整个pH 3--8范围内的形成速度更快。尿嘧啶C-5处的取代基对N-羟甲基化的热力学影响很小。讨论了N-羟甲基化合物作为前药的潜在用途。

  DOI：

  10.1002/jps.2600700803

文献信息

• N-hydroxymethyl Derivatives of Nitrogen Heterocycles as Possible Prodrugs I: N-hydroxymethylation of Uracils
  作者：Padam C. Bansal、Ian H. Pitman、Josiah N.S. Tam、Mathias Mertes、James J. Kaminski

  DOI：10.1002/jps.2600700803

  日期：1981.8

  constants for formation of N-1-hydroxymethyl derivatives were approximately twice those for formation of N-3-hydroxymethyl derivatives, and they were formed more rapidly throughout the pH 3--8 range. Substituents at C-5 of uracil had little effect on the thermodynamics of N-hydroxymethylation. The potential usefulness of N-hydroxymethyl compounds as prodrugs is discussed.

  制备了1，3-二羟甲基尿嘧啶，3-羟甲基-1-甲基尿嘧啶和1-羟甲基-3-甲基尿嘧啶的固体样品，并通过光谱分析确认了它们的结构。还研究了在甲醛水溶液中形成N-羟甲基化尿嘧啶的热力学和动力学。用于形成N-1-羟甲基衍生物的平衡常数大约是用于形成N-3-羟甲基衍生物的平衡常数的两倍，并且它们在整个pH 3--8范围内的形成速度更快。尿嘧啶C-5处的取代基对N-羟甲基化的热力学影响很小。讨论了N-羟甲基化合物作为前药的潜在用途。
• Derivatives Of Chemotherapeutic Agents With A Formaldehyde Releasing Moiety
  申请人：Nudelman Abraham

  公开号：US20070293517A1

  公开（公告）日：2007-12-20

  Novel conjugates of chemotherapeutic agents, which are designed so as to release formaldehyde or analogs thereof upon cleavage, processes of preparing same, pharmaceutical compositions containing same and methods utilizing same for treating medical conditions such as cancer, immune-mediated diseases, viral infections and diseases, bacterial infections and diseases, fungal infections and diseases, protozal infections and diseases and more, and particularly for treating such conditions which are characterized by drug resistance are provided.
• [EN] NOVEL DERIVATIVES OF CHEMOTHERAPEUTIC AGENTS AND USES THEREOF<br/>[FR] DERIVES D'AGENTS CHIMIOTHERAPEUTIQUES ET UTILISATIONS
  申请人：UNIV RAMOT

  公开号：WO2005120577A2

  公开（公告）日：2005-12-22

  Novel conjugates of chemotherapeutic agents, which are designed so as to release formaldehyde or analogs thereof upon cleavage, processes of preparing same, pharmaceutical compositions containing same and methods utilizing same for treating medical conditions such as cancer, immune-mediated diseases, viral infections and diseases, bacterial infections and diseases, fungal infections and diseases, protozal infections and diseases and more, and particularly for treating such conditions which are characterized by drug resistance are provided.
• The design and synthesis of ALS inhibitors from pharmacophore models
  作者：Jie Liu、Zhengming LI、Han Yan、Lingxiu Wang、Junpeng Chen

  DOI：10.1016/s0960-894x(99)00301-7

  日期：1999.7

  In search of new ALS inhibitors without the previous knowledge of receptor crystal structure, DISCO module was applied to produce 3D-pharmacophore models, which provided information to design novel molecules by 3D-database searching. Then a number of molecules were synthesized. Several of them have some ALS inhibitory activities. (C) 1999 Elsevier Science Ltd. All rights reserved.