pyridine ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl phosphonate | 1000863-50-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘧啶核苷
• 英文名称: pyridine ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl phosphonate
• CAS: 1000863-50-2
• 化学式: C₅H₅N*C₁₀H₁₄N₅O₆P
• 分子量: 410.326
• InChiKey: SIAOIAFTLCGIRL-HNPMAXIBSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.29
• 重原子数：
  28.0
• 可旋转键数：
  5.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  172.27
• 氢给体数：
  2.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  pyridine ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl phosphonate 、 齐多夫定 生成 di(3'-azido-3'-deoxy-5'-thymidinyl) tetraphosphate
  参考文献：
  名称：

  Synthesis of AZTp_Sp_CX2pp_SA and AZTp_Sp_CX2pp_SAZT:  Hydrolysis-Resistant Potential Inhibitors of the AZT Excision Reaction of HIV-1 RT

  摘要：

  We report an efficient, one-flask route for synthesis of AZTp(S)p(CX2)pp(s)A and AZTp(S)p(CX2)pp(s)AZT, where X = H and X = F. This route makes use of the differential susceptibility to oxidation of H-phosohonate mono- and diesters, to allow a series of sequential reactions without requiring isolation of intermediates. These compounds are hydrolysis-resistant versions of the AZTppppA that results from excision of AZT by AZT-resistant HIV reverse transcriptase (RT). This family of compounds may therefore be useful in further study of the AZT excision reaction, as well as in drug design.

  DOI：

  10.1021/ol7023746
• 作为产物：
  描述：

  吡啶 、 齐多夫定 在 水 作用下， 以 1,4-二氧六环 为溶剂， 反应 2.33h， 以78%的产率得到pyridine ((2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)tetrahydrofuran-2-yl)methyl phosphonate
  参考文献：
  名称：

  Synthesis of AZTp_Sp_CX2pp_SA and AZTp_Sp_CX2pp_SAZT:  Hydrolysis-Resistant Potential Inhibitors of the AZT Excision Reaction of HIV-1 RT

  摘要：

  We report an efficient, one-flask route for synthesis of AZTp(S)p(CX2)pp(s)A and AZTp(S)p(CX2)pp(s)AZT, where X = H and X = F. This route makes use of the differential susceptibility to oxidation of H-phosohonate mono- and diesters, to allow a series of sequential reactions without requiring isolation of intermediates. These compounds are hydrolysis-resistant versions of the AZTppppA that results from excision of AZT by AZT-resistant HIV reverse transcriptase (RT). This family of compounds may therefore be useful in further study of the AZT excision reaction, as well as in drug design.

  DOI：

  10.1021/ol7023746