5-[1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazol-4-yl]-pyrimidine-2,4-(1H,3H)-dione

• 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: 5-[1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazol-4-yl]-pyrimidine-2,4-(1H,3H)-dione
• 英文别名: 5-[1-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazol-4-yl]-1H-pyrimidine-2,4-dione
• 化学式: C₁₂H₁₄N₄O₅
• 分子量: 294.267
• InChiKey: JTJJVGAGVZLLLN-IVZWLZJFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.8
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  1-(2-deoxy-β-D-ribofuranos-1-yl)-4,5-diiodoimidazole 在 四(三苯基膦)钯 、 palladium 10% on activated carbon 、 乙基溴化镁 、 甲酸铵 、 sodium hydride 作用下， 以 四氢呋喃 、 乙二醇二甲醚 、 乙醇 为溶剂， 反应 25.17h， 生成 5-[1-(2-deoxy-β-D-ribofuranosyl)-1H-imidazol-4-yl]-pyrimidine-2,4-(1H,3H)-dione
  参考文献：
  名称：

  Synthetic Routes to a Series of Proximal and Distal 2′-Deoxy Fleximers

  摘要：

  Two series of innovative 2'-deoxy nucleoside analogues have been designed where the nucleobase has been split into its imidazole and pyrimidine subunits. This structural modification serves to introduce flexibility into the nucleobase scaffold while still retaining the elements required for recognition. The synthetic efforts to realize these analogues are described within.

  DOI：

  10.1055/s-0032-1316791

文献信息

• An expedient synthesis of flexible nucleosides via a regiocontrolled enzymatic glycosylation of functionalized imidazoles
  作者：S. Vichier-Guerre、L. Dugué、F. Bonhomme、S. Pochet

  DOI：10.1039/c7ob01850a

  日期：——

  leichmannii. Regiocontrolled glycosylation was also observed among several other imidazole derivatives studied, providing simple access to isomers not readily accessible by chemical routes. Finally, a series of flexible nucleosides was obtained in one step from 4- or 5-iodo-imidazole nucleosides by the Suzuki–Miyaura cross-coupling reaction with (hetero)aryl-boronic acids in aqueous media. Moreover, this chemoenzymatic

  C4-和C5-芳基化的2'-脱氧核糖基咪唑的多功能两步合成方法是使用酶促N-转糖基化，然后进行微波辅助的Pd催化的芳基化反应。我们在此报告了反应条件，该条件允许使用莱希曼氏乳杆菌的核苷N-脱氧核糖基转移酶处理4-碘咪唑的酶促糖基化反应中的区域选择性（N3对N1-异构体）。在其他研究的其他咪唑衍生物中也观察到了区域控制的糖基化作用，从而提供了通过化学途径不易获得的异构体的简便途径。最后，一步一步从4-或5-碘-咪唑核苷通过Suzuki-Miyaura与（杂）芳基-硼酸在水性介质中的交叉偶联反应一步获得了一系列柔性核苷。此外，这种化学酶法与一锅两步法兼容，可直接获得各种潜在的抗癌和抗病毒药物以及新的DNA构建基块。
• Synthetic Routes to a Series of Proximal and Distal 2′-Deoxy Fleximers
  作者：Katherine Seley-Radtke、Orrette Wauchope、Melvin Velasquez

  DOI：10.1055/s-0032-1316791

  日期：——

  Two series of innovative 2'-deoxy nucleoside analogues have been designed where the nucleobase has been split into its imidazole and pyrimidine subunits. This structural modification serves to introduce flexibility into the nucleobase scaffold while still retaining the elements required for recognition. The synthetic efforts to realize these analogues are described within.