10<2,3-dideoxy-5-<(hexadecyloxy)carbonyl>-β-D-glycero-pent-2-enefuranosyl>thymidine

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 10<2,3-dideoxy-5-<(hexadecyloxy)carbonyl>-β-D-glycero-pent-2-enefuranosyl>thymidine
• 英文别名: 10{2,3-dideoxy-5-[(hexadecyloxy)carbonyl]-β-D-glycero-pent-2-enefuranosyl}thymidine；hexadecyl [(2S,5R)-5-(5-methyl-2,4-dioxo-pyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl carbonate；hexadecyl [(2S,5R)-5-(5-methyl-2,4-dioxopyrimidin-1-yl)-2,5-dihydrofuran-2-yl]methyl carbonate
• 化学式: C₂₇H₄₄N₂O₆
• 分子量: 492.656
• InChiKey: FMMKYAKWPSPRHF-BJKOFHAPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.9
• 重原子数：
  35
• 可旋转键数：
  20
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.74
• 拓扑面积：
  94.2
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  司他夫定 以 乙腈 为溶剂， 反应 0.5h， 生成 10<2,3-dideoxy-5-<(hexadecyloxy)carbonyl>-β-D-glycero-pent-2-enefuranosyl>thymidine
  参考文献：
  名称：

  Synthesis and anti-HIV evaluation of D4T and D4T 5'-monophosphate prodrugs

  摘要：

  Several 5-monophosphate D4T derivatives and their analogues were synthesized as potential lipophilic prodrugs of D4T. Cholesteryl D4T phosphate diester and bis-5'-D4T phosphate inhibited HIV replication in CEM-Cl13 cells more efficiently than D4T itself as measured by the inhibition of cytopathic effect based on MTT assay or reverse transcriptase activity. The two compounds were devoid of toxicity on CEM-Cl13 cells at doses equal to 50 and 100 muM, respectively, which brought the selectivity index into the same range as AZT.

  DOI：

  10.1021/jm00059a006

文献信息

• Synthesis and anti-HIV evaluation of D4T and D4T 5'-monophosphate prodrugs
  作者：C. Sergheraert、C. Pierlot、A. Tartar、Y. Henin、M. Lemaitre

  DOI：10.1021/jm00059a006

  日期：1993.4

  Several 5-monophosphate D4T derivatives and their analogues were synthesized as potential lipophilic prodrugs of D4T. Cholesteryl D4T phosphate diester and bis-5'-D4T phosphate inhibited HIV replication in CEM-Cl13 cells more efficiently than D4T itself as measured by the inhibition of cytopathic effect based on MTT assay or reverse transcriptase activity. The two compounds were devoid of toxicity on CEM-Cl13 cells at doses equal to 50 and 100 muM, respectively, which brought the selectivity index into the same range as AZT.