4-(1,2,3,4,5,6,7,8,9,10-decahydro-10-(9((2R,3R_4S,5R)tetrahydro-3,4-dihydroxy-5-(hydroxymethyl)furan-2-yl)-9H-purin-6-yl)-8-imino-2,4,6trioxopirimido[4,5-b]naphtyridin-5-yl)benzonitrile | 1422054-86-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 4-(1,2,3,4,5,6,7,8,9,10-decahydro-10-(9((2R,3R_4S,5R)tetrahydro-3,4-dihydroxy-5-(hydroxymethyl)furan-2-yl)-9H-purin-6-yl)-8-imino-2,4,6trioxopirimido[4,5-b]naphtyridin-5-yl)benzonitrile
• 英文别名: 4-[2-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-5,7,11,13-tetraoxo-2,4,6,12,14-pentazatricyclo[8.4.0.03,8]tetradeca-1(10),3(8)-dien-9-yl]benzonitrile
• CAS: 1422054-86-1
• 化学式: C₂₆H₂₀N₁₀O₈
• 分子量: 600.507
• InChiKey: XQNVCRGEYIOPES-DEPGYJDFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.3
• 重原子数：
  44
• 可旋转键数：
  4
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.23
• 拓扑面积：
  257
• 氢给体数：
  7
• 氢受体数：
  13

反应信息

• 作为产物：
  描述：

  巴比妥酸 、 4-氰基苯甲醛 、 腺苷 在 phosphotungstic acid 作用下， 以 乙醇 为溶剂， 反应 12.0h， 以92%的产率得到4-(1,2,3,4,5,6,7,8,9,10-decahydro-10-(9((2R,3R_4S,5R)tetrahydro-3,4-dihydroxy-5-(hydroxymethyl)furan-2-yl)-9H-purin-6-yl)-8-imino-2,4,6trioxopirimido[4,5-b]naphtyridin-5-yl)benzonitrile
  参考文献：
  名称：

  Nucleosides as reagents in multicomponent reactions: one-pot synthesis of heterocyclic nucleoside analogues incorporating pyrimidine-fused rings

  摘要：

  In this study, a general and efficient protocol for the synthesis of new heterocyclic nucleoside analogues (HNAs), using a four-component coupling reaction of nucleosides, aldehydes, barbituric acid/2-thiobarbituric acid, or dimedone is described. The synthesized HNAs contain a pyrimidine-fused heterocycle coupled to the nucleoside via a C-N linkage. The nucleosides served as amine components and underwent the reaction in the presence of a catalytic amount of tungstophosphoric acid (H3PW12O40, TPA) in EtOH. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.11.003