1-((2R,4S,5S)-4-(4-(3-azidopropyl)-1H-1,2,3-triazol-1-yl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione | 1313201-70-5

• 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: 1-((2R,4S,5S)-4-(4-(3-azidopropyl)-1H-1,2,3-triazol-1-yl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
• CAS: 1313201-70-5
• 化学式: C₂₀H₃₂N₈O₄Si
• 分子量: 476.611
• InChiKey: MNZAASZPFUWRMN-LZLYRXPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.92
• 重原子数：
  33.0
• 可旋转键数：
  9.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.7
• 拓扑面积：
  152.79
• 氢给体数：
  1.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  1-((2R,4S,5S)-4-(4-(3-azidopropyl)-1H-1,2,3-triazol-1-yl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 在 4-二甲氨基吡啶 、 ammonium hydroxide 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 生成
  参考文献：
  名称：

  Synthesis and Anti-HIV Evaluation of 3′-Triazolo Nucleosides

  摘要：

  A series of hitherto unknown 3'--[1,2,3]-substituted triazolo-2',3'-dideoxypyrimidine nucleoside analogues of the anti-HIV 3'-azido-3'-deoxythymidine (AZT) were synthesized through catalyzed alkyne-azide 1,3-dipolar cycloaddition (Huisgen reaction). Those 3'-[1,2,3]-triazolo analogues bearing an azido alkyl chain were evaluated for their anti-HIV activity against HIV-1 in primary human lymphocytes as well as for their cytotoxicity in different cells. None of them inhibit HIV replication (EC50 20 M); two of them were converted to their triphosphate form to evaluate their HIV-RT inhibition.

  DOI：

  10.1080/15257770.2011.580291
• 作为产物：
  描述：

  在 sodium azide 、 三乙胺 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 生成 1-((2R,4S,5S)-4-(4-(3-azidopropyl)-1H-1,2,3-triazol-1-yl)-5-(((tert-butyldimethylsilyl)oxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione
  参考文献：
  名称：

  Synthesis and Anti-HIV Evaluation of 3′-Triazolo Nucleosides

  摘要：

  A series of hitherto unknown 3'--[1,2,3]-substituted triazolo-2',3'-dideoxypyrimidine nucleoside analogues of the anti-HIV 3'-azido-3'-deoxythymidine (AZT) were synthesized through catalyzed alkyne-azide 1,3-dipolar cycloaddition (Huisgen reaction). Those 3'-[1,2,3]-triazolo analogues bearing an azido alkyl chain were evaluated for their anti-HIV activity against HIV-1 in primary human lymphocytes as well as for their cytotoxicity in different cells. None of them inhibit HIV replication (EC50 20 M); two of them were converted to their triphosphate form to evaluate their HIV-RT inhibition.

  DOI：

  10.1080/15257770.2011.580291