1-(2-deoxy-β-D-ribofuranos-1-yl)-4,5-diiodoimidazole | 909869-57-4

• 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-ribofuranos-1-yl)-4,5-diiodoimidazole
• 英文别名: (2R,3S,5R)-5-(4,5-diiodoimidazol-1-yl)-2-(hydroxymethyl)oxolan-3-ol
• CAS: 909869-57-4
• 化学式: C₈H₁₀I₂N₂O₃
• 分子量: 435.988
• InChiKey: FBSWDLDUWBWMCP-KVQBGUIXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  15
• 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-ribofuranos-1-yl)-4,5-diiodoimidazole 在 乙基溴化镁 、 sodium hydride 作用下， 以 四氢呋喃 为溶剂， 反应 3.0h， 生成 1-[3,5-di-O-benzyl-2-deoxy-β-D-ribofuranosyl]-4-iodo-1H-imidazole
  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
• 作为产物：
  描述：

  1-[2-deoxy-3,5-di-O-p-toluoyl-β-D-ribofuranos-1-yl]-4,5-diiodoimidazole 在 sodium methylate 作用下， 以 甲醇 为溶剂， 反应 4.0h， 以87%的产率得到1-(2-deoxy-β-D-ribofuranos-1-yl)-4,5-diiodoimidazole
  参考文献：
  名称：

  Synthesis and biological evaluation of a series of thieno-expanded tricyclic purine 2′-deoxy nucleoside analogues

  摘要：

  Introducing structural diversity into the nucleoside scaffold for use as potential chemotherapeutics has long been considered an important approach to drug design. In that regard, we have designed and synthesized a number of innovative 2'-deoxy expanded nucleosides where a heteroaromatic thiophene spacer ring has been inserted in between the imidazole and pyrimidine ring systems of the natural purine scaffold. The synthetic efforts towards realizing the expanded 2'-deoxy-guanosine and -adenosine tricyclic analogues as well as the preliminary biological results are presented herein. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2012.03.004

文献信息

• Synthesis and Properties of Oligonucleotides with Iodo-Substituted Aromatic Aglycons:  Investigation of Possible Halogen Bonding Base Pairs
  作者：Ryuya Tawarada、Kohji Seio、Mitsuo Sekine

  DOI：10.1021/jo701634t

  日期：2008.1.1

  [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.