1-[(2R,4S,5S)-4-[4-(azidomethyl)triazol-1-yl]-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione | 1313201-74-9

• 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-(azidomethyl)triazol-1-yl]-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-dione
• CAS: 1313201-74-9
• 化学式: C₁₂H₁₄N₈O₄
• 分子量: 334.294
• InChiKey: NBPVEKXEFXSDGM-IQJOONFLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.9
• 重原子数：
  24
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  124
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  1-((2R,4S,5S)-4-azido-5-((tert-butyldimethylsilyloxy)methyl)tetrahydrofuran-2-yl)pyrimidine-2,4(1H,3H)-dione 在 sodium azide 、 四丁基氟化铵 、 copper(II) sulfate 、 sodium ascorbate 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 水 、 N,N-二甲基甲酰胺 、 叔丁醇 为溶剂， 生成 1-[(2R,4S,5S)-4-[4-(azidomethyl)triazol-1-yl]-5-(hydroxymethyl)oxolan-2-yl]pyrimidine-2,4-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

文献信息

• Synthesis and Anti-HIV Evaluation of 3′-Triazolo Nucleosides
  作者：Vincent Roy、Aleksandr Obikhod、Hong-Wang Zhang、Steven J. Coats、Brian D. Herman、Nicolas Sluis-Cremer、Luigi A. Agrofoglio、Raymond F. Schinazi

  DOI：10.1080/15257770.2011.580291

  日期：2011.4

  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.