1-((2R,4S,5R)-4-((4-methoxybenzyl)oxy)-5-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran-2-yl)-1H-imidazo[4',5':4,5]thieno[3,2-d]pyrimidin-5(6H)-one | 1373759-40-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 噻吩并嘧啶酮衍生物
• 英文名称: 1-((2R,4S,5R)-4-((4-methoxybenzyl)oxy)-5-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran-2-yl)-1H-imidazo[4',5':4,5]thieno[3,2-d]pyrimidin-5(6H)-one
• CAS: 1373759-40-0
• 化学式: C₂₈H₂₈N₄O₆S
• 分子量: 548.62
• InChiKey: QXTXQTOYPFFHFF-YTFSRNRJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.44
• 重原子数：
  39.0
• 可旋转键数：
  10.0
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  109.72
• 氢给体数：
  1.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5R)-4-((4-methoxybenzyl)oxy)-5-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran-2-yl)-1H-imidazo[4',5':4,5]thieno[3,2-d]pyrimidin-5(6H)-one 在 Raney nickel 作用下， 以 乙醇 为溶剂， 反应 18.0h， 以70%的产率得到6-{1-[2-deoxy-3,5-di-O-(4-methoxybenzyl)-β-D-ribofuranosyl]-1H-imidazol-5-yl}pyrimidin-4(3H)-one
  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-β-D-ribofuranos-1-yl)-4,5-diiodoimidazole 在 乙基溴化镁 、 盐酸羟胺 、 sodium ethanolate 、 sodium hydride 、 碳酸氢钠 、 potassium carbonate 、 N,N'-羰基二咪唑 作用下， 以 四氢呋喃 、 乙醚 、 乙醇 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 46.75h， 生成 1-((2R,4S,5R)-4-((4-methoxybenzyl)oxy)-5-(((4-methoxybenzyl)oxy)methyl)tetrahydrofuran-2-yl)-1H-imidazo[4',5':4,5]thieno[3,2-d]pyrimidin-5(6H)-one
  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