(1S)-N-tert-butoxycarbonyl-1'-C-{4-methoxypyrrolo[3,2-d]pyrimidin-7-yl}-1',4'-dideoxy-1',4'-imino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribitol | 917595-34-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯并嘧啶类
• 英文名称: (1S)-N-tert-butoxycarbonyl-1'-C-{4-methoxypyrrolo[3,2-d]pyrimidin-7-yl}-1',4'-dideoxy-1',4'-imino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribitol
• CAS: 917595-34-7
• 化学式: C₂₉H₅₀N₄O₆Si₂
• 分子量: 606.91
• InChiKey: QVHIUKMABPEENF-SMIHKQSGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.97
• 重原子数：
  41.0
• 可旋转键数：
  6.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.76
• 拓扑面积：
  108.03
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  (1S)-N-tert-butoxycarbonyl-1'-C-{4-methoxypyrrolo[3,2-d]pyrimidin-7-yl}-1',4'-dideoxy-1',4'-imino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribitol 在 盐酸 作用下， 以 甲醇 、 水 为溶剂， 反应 3.0h， 以83%的产率得到(1R)-(9-deazahypoxanthin-9-yl)-1,2,4-trideoxy-1,4-imino-D-erythro-pentitol hydrochloride
  参考文献：
  名称：

  Synthesis and Pharmacokinetic and Pharmacodynamic Evaluation of the Forodesine HCl Analog BCX-3040

  摘要：

  Forodesine HCl is a potent inhibitor of the enzyme purine nucleoside phosphorylase (PNP) and is currently in clinical trials for the treatment of leukemia and lymphoma. Animal models indicated that forodesine HCl would have low oral bioavailability in humans and it was initially developed as an intravenous formulation. We were interested in identifying analogs of forodesine HCl with improved oral bioavailability. The 2'-deoxy analog (BCX-3040) was synthesized and its pharmacokinetic and pharmacodynamic properties compared with forodesine HCl.

  DOI：

  10.1080/15257770500267246
• 作为产物：
  描述：

  2-(5-benzyloxymethyl-4-methoxy-5H-pyrrolo[3,2-d]pyrimidin-7-yl)-5,5,7,7-tetraisopropyl-tetrahydro-4,6,8-trioxa-1-aza-5,7-disila-cyclopentacyclooctene-1-carboxylic acid tert-butyl ester 在 palladium dihydroxide 氨 、 氢气 作用下， 以 乙醇 、 水 为溶剂， 反应 1.5h， 以90%的产率得到(1S)-N-tert-butoxycarbonyl-1'-C-{4-methoxypyrrolo[3,2-d]pyrimidin-7-yl}-1',4'-dideoxy-1',4'-imino-2'-deoxy-3',5'-O-(1,1,3,3-tetraisopropyldisiloxane-1,3-diyl)-D-ribitol
  参考文献：
  名称：

  Synthesis and Pharmacokinetic and Pharmacodynamic Evaluation of the Forodesine HCl Analog BCX-3040

  摘要：

  Forodesine HCl is a potent inhibitor of the enzyme purine nucleoside phosphorylase (PNP) and is currently in clinical trials for the treatment of leukemia and lymphoma. Animal models indicated that forodesine HCl would have low oral bioavailability in humans and it was initially developed as an intravenous formulation. We were interested in identifying analogs of forodesine HCl with improved oral bioavailability. The 2'-deoxy analog (BCX-3040) was synthesized and its pharmacokinetic and pharmacodynamic properties compared with forodesine HCl.

  DOI：

  10.1080/15257770500267246