2-氨基-4-羟基-6-碘嘧啶 | 59524-88-8

• 物质功能分类: 医药中间体 - 杂环化合物 - 嘧啶类化合物
• 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: 2-氨基-4-羟基-6-碘嘧啶
• 英文名称: 2-amino-6-iodo-pyrimidin-4(3H)-one
• 英文别名: 2-amino-6-iodopyrimidin-4-one；2-amino-6-iodo-3H-pyrimidin-4-one；2-Amino-6-jod-3H-pyrimidin-4-on；2-Amino-6-iodopyrimidin-4-ol；2-amino-4-iodo-1H-pyrimidin-6-one
• CAS: 59524-88-8
• 化学式: C₄H₄IN₃O
• 分子量: 237.0
• InChiKey: VKVUNHPVRFQNBN-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.6
• 重原子数：
  9
• 可旋转键数：
  0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-氨基-4-羟基-6-碘嘧啶 、 3-甲基苯硼酸 在 (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride 、 potassium phosphate 、 三环己基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-amino-6-m-tolylpyrimidin-4-ol
  参考文献：
  名称：

  HTS，然后进行基于NMR的反向筛选。发现和优化作为黄嘌呤氧化酶可逆和竞争性抑制剂的嘧啶酮

  摘要：

  描述了新型，非嘌呤的黄嘌呤氧化酶抑制剂的鉴定。经过高通量筛选活动后，基于NMR的反筛选用于区分活性物，这些活性物以可逆方式与XO相互作用，与分析伪像分离。该方法将嘧啶酮1鉴定为可逆的竞争性抑制剂，具有良好的铅样性质。导致先头运动获得化合物41，一种hXO的纳摩尔抑制剂，口服给药后在高尿酸血症大鼠模型中具有功效。

  DOI：

  10.1016/j.bmcl.2014.01.050
• 作为产物：
  描述：

  2-氨基-4,6-二氯嘧啶 在 氢碘酸 、 sodium iodide 作用下， 以 丙酮 为溶剂， 反应 48.0h， 以86%的产率得到2-氨基-4-羟基-6-碘嘧啶
  参考文献：
  名称：

  Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines

  摘要：

  准备了几种作为抗病毒活性的2,4-二氨基-6-[2-(磷酸甲氧基)乙氧基]嘧啶的饱和和不饱和的碳酰类似物6-[(磷酸甲氧基)烷基]嘧啶和6-[(磷酸甲氧基)炔基]嘧啶。它们的合成关键步骤是成功应用Sonogashira交叉偶联反应。将C-O基团替换为C-C键导致了生物活性的丧失。

  DOI：

  10.1135/cccc20050247

文献信息

• Sonogashira Cross-Coupling in the Synthesis of Acyclic Nucleoside Phosphonates: Preparation of 6-[(Phosphonomethoxy)alkynyl]- and 6-[(Phosphonomethoxy)alkyl]pyrimidines
  作者：Dana Hocková、Milena Masojídková、Antonín Holý

  DOI：10.1135/cccc20050247

  日期：——

  Several 6-[(phosphonomethoxy)alkyl]pyrimidines and 6-[(phosphonomethoxy)alkynyl]pyrimidines were prepared as saturated and unsaturated carba-analogues of antivirally active 2,4-diamino-6-[2-(phosphonomethoxy)ethoxy]pyrimidine. As the key step of their synthesis the Sonogashira cross-coupling reaction was successfully applied. The replacement of the C-O moiety by the C-C bond resulted in the loss of biological activity.

  准备了几种作为抗病毒活性的2,4-二氨基-6-[2-(磷酸甲氧基)乙氧基]嘧啶的饱和和不饱和的碳酰类似物6-[(磷酸甲氧基)烷基]嘧啶和6-[(磷酸甲氧基)炔基]嘧啶。它们的合成关键步骤是成功应用Sonogashira交叉偶联反应。将C-O基团替换为C-C键导致了生物活性的丧失。
• Buettner, Chemische Berichte, 1903, vol. 36, p. 2234
  作者：Buettner

  DOI：——

  日期：——
• Design and Synthesis of a DNA-Like Structure Composed of Alkynyl C-Nucleotide with 2-Aminopyrimidin-4-one as a Nucleobase
  作者：Junya Chiba、Masahiko Inouye、Fumihiro Kurosaki

  DOI：10.3987/com-18-s(t)53

  日期：——

  A heterocyclic compound, 2-aminopyrimidin-4-one, was found to be a new candidate of a non-natural nucleobase that forms a novel base pair by self-dimerization. 2-Aminopyrimidin-4-one was connected to a deoxyribose through an acetylene linkage. The non-natural nucleoside was derivatized to its phosphoramidite that could be subjected to a conventional solid-phase DNA synthesis. The solid-phase auto-synthesis successfully afforded a non-natural DNA-like oligomer bearing 2-aminopyrimidin-4-one as a nucleobase. The synthetic oligomer exhibited reversible formation of a higher-order structure that would be a duplex like natural DNA. The present study means creation of a novel artificial DNA-like system with unordinary odd numbers of genetic alphabets.
• HIVAYAMA T.; KAMADA M.; MIMURA M.; TSURUMI H., CHEM. AND PHARM. BULL. <CPBT-AL>, 1976, 24, NO 3, 507-514
  作者：HIVAYAMA T.、 KAMADA M.、 MIMURA M.、 TSURUMI H.

  DOI：——

  日期：——
• 2-Amino-6-iodo-4-tosyloxypyrimidine: a versatile key intermediate for regioselective functionalization of 2-aminopyrimidines in 4- and 6-positions
  作者：Pascal Benderitter、João Xavier de Araújo Júnior、Martine Schmitt、Jean-Jacques Bourguignon

  DOI：10.1016/j.tet.2007.07.100

  日期：2007.12

  2-Amino-6-iodo-4-tosyloxypyrimidine, easily prepared from commercially available material, is a key intermediate for the preparation of differentially substituted 2-aminopyrimidines by means of sequenced Suzuki and/or Sonogashira reactions. (c) 2007 Elsevier Ltd. All rights reserved.