bis(2',3'-dideoxy-3'-fluoro-4-thiothymidine)-5',5'-P1,P2-pyrophosphate | 1241964-76-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二嗪类
• 英文名称: bis(2',3'-dideoxy-3'-fluoro-4-thiothymidine)-5',5'-P1,P2-pyrophosphate
• 英文别名: [[(2R,3S,5R)-3-fluoro-5-(5-methyl-2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methoxy-hydroxyphosphoryl] [(2R,3S,5R)-3-fluoro-5-(5-methyl-2-oxo-4-sulfanylidenepyrimidin-1-yl)oxolan-2-yl]methyl hydrogen phosphate
• CAS: 1241964-76-0
• 化学式: C₂₀H₂₆F₂N₄O₁₁P₂S₂
• 分子量: 662.523
• InChiKey: FAQBMEIKEULCKQ-KPRKPIBOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1
• 重原子数：
  41
• 可旋转键数：
  10
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  250
• 氢给体数：
  4
• 氢受体数：
  15

反应信息

• 作为反应物：
  描述：

  bis(2',3'-dideoxy-3'-fluoro-4-thiothymidine)-5',5'-P1,P2-pyrophosphate 在 sodium iodide 作用下， 以 甲醇 、 丙酮 为溶剂， 以33 mg的产率得到bis(2',3'-dideoxy-3'-fluoro-4-thiothymidine)-5',5'-P1,P2-pyrophosphate disodium salt
  参考文献：
  名称：

  Synthesis, Biological Properties and Anti-HIV-1 Activity of New Pyrimidine P₁,P₂-Dinucleotides

  摘要：

  New homo- and hetero-P1,P2-dinucleotides were prepared with the use of multistep procedures starting from the monophosphates of 3'-fluoro-2-thiothymidine, 3'-fluoro-4-thiothymidine, AZT and 1-[(2-hydroxyethoxy)-methyl-5-propyl-6-phenylselenenyl]uracil. Anti-HIV properties of the synthesized P1,P2-dinucleotides were evaluated against laboratory syncytia inducing strain HIV-1 in CEM-T4 cells. Anti-HIV activities were in the range of 5-45 nM, and therapeutic indexes were higher than 4666-14000. Interactions of the above mentioned compounds with recombinant HIV-1 reverse transcriptase were also investigated. The obtained results point to reverse transcriptase inhibition, with somewhat lower inhibitory activity than that of their parental nucleoside-5'-triphosphates. Compound 6 may be regarded as a potent anti-HIV/AIDS drug.

  DOI：

  10.1080/15257771003738642
• 作为产物：
  描述：

  在 吡啶 、 4-二甲氨基吡啶 、 对甲苯磺酰氯 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 24.0h， 生成 bis(2',3'-dideoxy-3'-fluoro-4-thiothymidine)-5',5'-P1,P2-pyrophosphate
  参考文献：
  名称：

  Synthesis, Biological Properties and Anti-HIV-1 Activity of New Pyrimidine P₁,P₂-Dinucleotides

  摘要：

  New homo- and hetero-P1,P2-dinucleotides were prepared with the use of multistep procedures starting from the monophosphates of 3'-fluoro-2-thiothymidine, 3'-fluoro-4-thiothymidine, AZT and 1-[(2-hydroxyethoxy)-methyl-5-propyl-6-phenylselenenyl]uracil. Anti-HIV properties of the synthesized P1,P2-dinucleotides were evaluated against laboratory syncytia inducing strain HIV-1 in CEM-T4 cells. Anti-HIV activities were in the range of 5-45 nM, and therapeutic indexes were higher than 4666-14000. Interactions of the above mentioned compounds with recombinant HIV-1 reverse transcriptase were also investigated. The obtained results point to reverse transcriptase inhibition, with somewhat lower inhibitory activity than that of their parental nucleoside-5'-triphosphates. Compound 6 may be regarded as a potent anti-HIV/AIDS drug.

  DOI：

  10.1080/15257771003738642