5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-3'-isocyanouridine | 124288-71-7

• 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: 5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-3'-isocyanouridine
• CAS: 124288-71-7
• 化学式: C₁₆H₂₅N₃O₄Si
• 分子量: 351.478
• InChiKey: MFLDVICVGCSZCO-OUCADQQQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.13
• 重原子数：
  24.0
• 可旋转键数：
  4.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  77.68
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-3'-isocyanouridine 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 反应 0.33h， 以88%的产率得到1-[(2R,4S,5S)-5-(羟基甲基)-4-异氰基四氢呋喃-2-基]嘧啶-2,4-二酮
  参考文献：
  名称：

  Synthesis, antiretrovirus effects and phosphorylation kinetics of 3'-isocyano-3'-deoxythymidine and 3'-isocyano-2',3'-dideoxyuridine

  摘要：

  The silylated AzddThd 5 and AzddUrd 6 prepared from 2,3'-anhydronucleoside derivatives 3 and 4 were transformed to formamides 7 and 8 by using the sequence RN3----RN = P(C6H5)----RNHCHO. Formamides 7 and 8 were dehydrated to the protected 3'-isocyano derivatives 9 and 10; deblocking gave 11 and 12. Neither 3'-isocyano-3'-deoxythymidine (11) nor 3'-isocyano-2',3'-dideoxyuridine (12) showed anti-HIV activity at noncytotoxic concentrations. ddThd derivative 11 was considerably more toxic to MT-4 cells than ddUrd derivative 12; it also had a much greater affinity (Ki) for MT-4 cell dThd kinase than ddUrd derivative 12. Both compounds appear to be linear mixed-type inhibitors of MT-4 cell dThd kinase.

  DOI：

  10.1021/jm00164a059
• 作为产物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-3'-formamidouridine 在 二异丙胺 、 三氯氧磷 作用下， 以 二氯甲烷 为溶剂， 以47%的产率得到5'-O-(tert-butyldimethylsilyl)-2',3'-dideoxy-3'-isocyanouridine
  参考文献：
  名称：

  Synthesis, antiretrovirus effects and phosphorylation kinetics of 3'-isocyano-3'-deoxythymidine and 3'-isocyano-2',3'-dideoxyuridine

  摘要：

  The silylated AzddThd 5 and AzddUrd 6 prepared from 2,3'-anhydronucleoside derivatives 3 and 4 were transformed to formamides 7 and 8 by using the sequence RN3----RN = P(C6H5)----RNHCHO. Formamides 7 and 8 were dehydrated to the protected 3'-isocyano derivatives 9 and 10; deblocking gave 11 and 12. Neither 3'-isocyano-3'-deoxythymidine (11) nor 3'-isocyano-2',3'-dideoxyuridine (12) showed anti-HIV activity at noncytotoxic concentrations. ddThd derivative 11 was considerably more toxic to MT-4 cells than ddUrd derivative 12; it also had a much greater affinity (Ki) for MT-4 cell dThd kinase than ddUrd derivative 12. Both compounds appear to be linear mixed-type inhibitors of MT-4 cell dThd kinase.

  DOI：

  10.1021/jm00164a059