(2R-cis)-tetrahydro-4-<6-(methylamino)-9H-purin-9-yl>-2-furanmethanol | 141585-89-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: (2R-cis)-tetrahydro-4-<6-(methylamino)-9H-purin-9-yl>-2-furanmethanol
• CAS: 141585-89-9
• 化学式: C₁₁H₁₅N₅O₂
• 分子量: 249.272
• InChiKey: PWNLKPHUDVBLHG-YUMQZZPRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.19
• 重原子数：
  18.0
• 可旋转键数：
  3.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  85.09
• 氢给体数：
  2.0
• 氢受体数：
  7.0

反应信息

• 作为反应物：
  描述：

  (2R-cis)-tetrahydro-4-<6-(methylamino)-9H-purin-9-yl>-2-furanmethanol 在 ammonium hydroxide 、 硫脲 作用下， 以 丙醇 、 水 为溶剂， 反应 3.0h， 生成 (2R-cis)-tetrahydro-4-<6-(methylthio)-9H-purin-9-yl>-2-furanmethanol
  参考文献：
  名称：

  Synthesis and anti-HIV activity of isonucleosides

  摘要：

  A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compounds prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.

  DOI：

  10.1021/jm00091a001
• 作为产物：
  描述：

  3-deoxy-1,2-O-(1-methylethylidene)-α-D-erythro-pentofuranose 4-methylbenzenesufonate 在 palladium on activated charcoal 吡啶 、 sodium tetrahydroborate 、 sodium azide 、 氢气 、 溶剂黄146 、 三乙胺 、 三氟乙酸 作用下， 以 1,4-二氧六环 、 甲醇 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 反应 412.5h， 生成 (2R-cis)-tetrahydro-4-<6-(methylamino)-9H-purin-9-yl>-2-furanmethanol
  参考文献：
  名称：

  Synthesis and anti-HIV activity of isonucleosides

  摘要：

  A series of isomeric 2',3'-dideoxynucleosides which contains a modified carbohydrate moiety has been prepared. This class of compounds was designed to mimic the activity of known anti-HIV dideoxynucleosides, while imparting enhanced chemical and enzymatic stability. Isonucleosides containing the standard heterocyclic bases (A, C, G, T) were synthesized via nucleophilic addition of the base to an isomeric sugar unit. Modified derivatives were generated by manipulation of the intact isonucleoside. Two of the compounds prepared, iso-ddA (1) and iso-ddG (6), exhibit significant and selective anti-HIV activity, as well as beneficial hydrolytic stability.

  DOI：

  10.1021/jm00091a001