O-p-nitrophenyl-5'-phosphodiester allopurinol riboside | 152715-10-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷酸
• 英文名称: O-p-nitrophenyl-5'-phosphodiester allopurinol riboside
• CAS: 152715-10-1
• 化学式: C₁₆H₁₆N₅O₁₀P
• 分子量: 469.304
• InChiKey: VQHVRMFRGWDRDR-BRXULGCHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.26
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  212.42
• 氢给体数：
  4.0
• 氢受体数：
  13.0

反应信息

• 作为反应物：
  描述：

  O-p-nitrophenyl-5'-phosphodiester allopurinol riboside 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 2.0h， 生成
  参考文献：
  名称：

  Synthesis of an allopurinol riboside-mannosylated poly-l-lysine conjugate

  摘要：

  The synthesis of a mannosylated carrier used as a drug delivery system to target specifically an antileishmanial drug allopurinol riboside [4-hydroxy-1-beta-D-ribofuranosyl-1H-pyrazolo(3,4-d) pyrimidine] into Leishmania donovani infected macrophages via their membrane lectin is described. The synthetic construct is made of a poly-L-lysine backbone, partially acylated with delta-gluconolactone to enhance its water-solubility and substituted with glycyl-glycine asa spacer arm. O-p-phenylisothiocyanate-5'-phosphodiester derivatives of allopurinol riboside and of inosine were synthesized and attached to the spacer arm, then the remaining spacer arms were substituted by reaction with phenyl acetate mannosyl residues.

  DOI：

  10.1016/s0040-4020(01)87974-6
• 作为产物：
  描述：

  4-硝基苯二氯化磷 、 别嘌呤醇核糖苷 在 吡啶 作用下， 反应 1.0h， 以56%的产率得到O-p-nitrophenyl-5'-phosphodiester allopurinol riboside
  参考文献：
  名称：

  Synthesis of an allopurinol riboside-mannosylated poly-l-lysine conjugate

  摘要：

  The synthesis of a mannosylated carrier used as a drug delivery system to target specifically an antileishmanial drug allopurinol riboside [4-hydroxy-1-beta-D-ribofuranosyl-1H-pyrazolo(3,4-d) pyrimidine] into Leishmania donovani infected macrophages via their membrane lectin is described. The synthetic construct is made of a poly-L-lysine backbone, partially acylated with delta-gluconolactone to enhance its water-solubility and substituted with glycyl-glycine asa spacer arm. O-p-phenylisothiocyanate-5'-phosphodiester derivatives of allopurinol riboside and of inosine were synthesized and attached to the spacer arm, then the remaining spacer arms were substituted by reaction with phenyl acetate mannosyl residues.

  DOI：

  10.1016/s0040-4020(01)87974-6