[[[[(2r,3s,4r,5r)-5-(6-Aminopurin-9-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl] [(2s,3s,5r)-3-Azido-5-(5-Methyl-2,4-Dioxo-Pyrimidin-1-Yl)oxolan-2-Yl]methyl Hydrogen Phosphate | 639476-95-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - （5'->5'）-二核苷酸
• 英文名称: [[[[(2r,3s,4r,5r)-5-(6-Aminopurin-9-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl] [(2s,3s,5r)-3-Azido-5-(5-Methyl-2,4-Dioxo-Pyrimidin-1-Yl)oxolan-2-Yl]methyl Hydrogen Phosphate
• 英文别名: [[(2R,3S,4R,5R)-5-(6-aminopurin-9-yl)-3,4-dihydroxyoxolan-2-yl]methoxy-hydroxyphosphoryl] [[[(2S,3S,5R)-3-azido-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl]oxy-hydroxyphosphoryl] hydrogen phosphate
• CAS: 639476-95-2
• 化学式: C₂₀H₂₈N₁₀O₁₉P₄
• 分子量: 836.393
• InChiKey: NHJROJSMKQZWCP-SLFMBYJQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -5.8
• 重原子数：
  53
• 可旋转键数：
  15
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  388
• 氢给体数：
  8
• 氢受体数：
  25

反应信息

• 作为产物：
  描述：

  齐多夫定 、 5'-腺嘌呤核苷酸 生成 [[[[(2r,3s,4r,5r)-5-(6-Aminopurin-9-Yl)-3,4-Dihydroxy-Oxolan-2-Yl]methoxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl]oxy-Hydroxy-Phosphoryl] [(2s,3s,5r)-3-Azido-5-(5-Methyl-2,4-Dioxo-Pyrimidin-1-Yl)oxolan-2-Yl]methyl Hydrogen Phosphate
  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

文献信息

• Synthesis of AZTp_Sp_CX2pp_SA and AZTp_Sp_CX2pp_SAZT:  Hydrolysis-Resistant Potential Inhibitors of the AZT Excision Reaction of HIV-1 RT
  作者：Qianwei Han、Stefan G. Sarafianos、Eddy Arnold、Michael A. Parniak、Barbara L. Gaffney、Roger A. Jones

  DOI：10.1021/ol7023746

  日期：2007.12.1

  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.