5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-formamidothymidine | 124288-68-2

• 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: 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-formamidothymidine
• 英文别名: N-[(2S,3S,5R)-2-[[tert-butyl(dimethyl)silyl]oxymethyl]-5-(5-methyl-2,4-dioxopyrimidin-1-yl)oxolan-3-yl]formamide
• CAS: 124288-68-2
• 化学式: C₁₇H₂₉N₃O₅Si
• 分子量: 383.52
• InChiKey: NKZWUBVIUQYMQS-BFHYXJOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.27
• 重原子数：
  26.0
• 可旋转键数：
  6.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  102.42
• 氢给体数：
  2.0
• 氢受体数：
  6.0

反应信息

• 作为反应物：
  描述：

  5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-formamidothymidine 在 四丁基氟化铵 、 二异丙胺 、 三氯氧磷 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 1.5h， 生成 1-[(2R,4S,5S)-5-(羟基甲基)-4-异氰基四氢呋喃-2-基]-5-甲基嘧啶-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-(t-butyldimethylsilyl)-2,3'-anhydro-1-(2'-deoxy-β-D-threo-pentofuranosyl)thymine 在 sodium azide 、 三苯基膦 作用下， 以 水 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 15.0h， 生成 5'-O-(tert-butyldimethylsilyl)-3'-deoxy-3'-formamidothymidine
  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

文献信息

• HIEBL, JOHANN;ZBIRAL, ERICH;BALZARINI, JAN;DE, CLERCQ ERIK, J. MED. CHEM., 33,(1990) N, C. 845-848
  作者：HIEBL, JOHANN、ZBIRAL, ERICH、BALZARINI, JAN、DE, CLERCQ ERIK

  DOI：——

  日期：——
• MATSUDA, AKIRA;SATOH, MUTSUMI;UEDA, TOHRU;MACHIDA, HARUHIKO;SASAKI, TAKUM+, NUCLEOSIDES AND NUCLEOTIDES, 9,(1990) N, C. 587-597
  作者：MATSUDA, AKIRA、SATOH, MUTSUMI、UEDA, TOHRU、MACHIDA, HARUHIKO、SASAKI, TAKUM+

  DOI：——

  日期：——