1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-1H-imidazole | 909869-60-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-1H-imidazole
• 英文别名: (2R,3S,5R)-2-(hydroxymethyl)-5-(4-iodoimidazol-1-yl)oxolan-3-ol
• CAS: 909869-60-9
• 化学式: C₈H₁₁IN₂O₃
• 分子量: 310.091
• InChiKey: QGOMLGPETXKATP-SHYZEUOFSA-N

物化性质

• 沸点：
  558.4±50.0 °C(Predicted)
• 密度：
  2.23±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  14
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  67.5
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-1H-imidazole 在 磷酸三甲酯 、 palladium diacetate 、 caesium carbonate 、 三氯氧磷 作用下， 以 水 、 乙腈 为溶剂， 反应 1.66h， 生成
  参考文献：
  名称：

  2′-Deoxyribonucleoside 5′-triphosphates bearing 4-phenyl and 4-pyrimidinyl imidazoles as DNA polymerase substrates

  摘要：

  已经制定了一种用于制备含有4-芳基咪唑的2'-脱氧核糖核苷5'-三磷酸的模块化策略。这些新的DNA构建块是DNA聚合酶的底物。

  DOI：

  10.1039/c8ob02464b
• 作为产物：
  描述：

  1-[2-deoxy-5-O-(4,4'-dimethoxytrityl)-β-D-ribofuranos-1-yl]-4-iodoimidazole 在 溶剂黄146 作用下， 反应 4.0h， 以83%的产率得到1-(2-Deoxy-β-D-ribofuranosyl)-4-iodo-1H-imidazole
  参考文献：
  名称：

  Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons:  Investigation of Possible Halogen Bonding Base Pairs

  摘要：

  [GRAPHICS]Ab initio calculations of halogen bond energies of artificial base pairs constructed between iodinated aromatic nucleobase mimics and nitrogen-containing acceptor molecules such as pyridine and imidazole suggest that modified base pairs are converted to optimized planar base pairs with weak Delta E values of -0.19 to -3.93 kcal/mol. To evaluate the contribution of halogen bonding toward duplex stabilization of such modified nucleobase mimics introduced into artificial base pairs, we synthesized three C-nucleoside analogues 1-3 with several iodinated aromatic rings and an imidazole nucleoside derivative 4 and incorporated them into oligodeoxynucleotides. Hybridization studies of modified oligodeoxynucleotides incorporating iodoaromatic bases showed their unique universal base-like ability; however, no indication of halogen bond formation was observed. A more sophisticated design is required for the development of new base pairs stabilized by halogen bonding.

  DOI：

  10.1021/jo701634t

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。