6'-carba-2',3'-dideoxy-3'-thiocyanatothymidine | 883742-39-0

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 核苷和核苷酸类似物
• 英文名称: 6'-carba-2',3'-dideoxy-3'-thiocyanatothymidine
• 英文别名: [(1S,2R,4R)-2-(hydroxymethyl)-4-(5-methyl-2,4-dioxopyrimidin-1-yl)cyclopentyl] thiocyanate
• CAS: 883742-39-0
• 化学式: C₁₂H₁₅N₃O₃S
• 分子量: 281.335
• InChiKey: GNAXJRILNAPXKB-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  119
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  6'-carba-2',3'-dideoxy-3'-thiocyanatothymidine 在 叔丁基过氧化氢 、 水 、 三乙胺 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 50.0h， 生成 carba-3'-thiocyanato-2'-deoxythymidine monophosphate
  参考文献：
  名称：

  SYNTHESIS OF CARBOCYCLIC NUCLEOTIDES AS POTENTIAL SUBSTRATES FOR THYMIDYLATE KINASE

  摘要：

  Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.

  DOI：

  10.1081/ncn-200060251
• 作为产物：
  描述：

  carba-3'-thiocyanato-2'-deoxythymidine 在 苯磺酸 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 以79%的产率得到6'-carba-2',3'-dideoxy-3'-thiocyanatothymidine
  参考文献：
  名称：

  SYNTHESIS OF CARBOCYCLIC NUCLEOTIDES AS POTENTIAL SUBSTRATES FOR THYMIDYLATE KINASE

  摘要：

  Enantiomerically pure carbocyclic 2'-deoxy-3'-azidothymidine monophosphate (AZTMP) and carba-2'deoxy-3'-thiocyanatothymidine monophosphate were synthesized to study their behavior toward their phosphorylation by thymidylate kinase. The nucleotides were synthesized starting from the parent nucleosides by an alkaline hydrolysis of the corresponding cycloSal-phosphate triesters.

  DOI：

  10.1081/ncn-200060251

文献信息

• Synthesis and Antiviral Evaluation of Carbocyclic 3′-Azidothymidine (AZT) Analogues and TheircycloSal-Phosphate Triesters
  作者：Olaf R. Ludek、Jan Balzarini、Chris Meier

  DOI：10.1002/ejoc.200500719

  日期：2006.2

  Carbocyclic analogues of the anti-HIV dideoxynucleoside 3′-azido-3′-deoxythymidine AZT (1) were synthesized. Starting from the enantiomerically pure carbocyclic 2′-deoxythymidine 2, four different carbocyclic AZT analogues 2,4–6 were prepared. Moreover, the nucleoside analogues were converted into their membrane-permeable cycloSal-phosphate triesters. All compounds were tested in vitro for their anti-HIV

  合成了抗 HIV 双脱氧核苷 3'-叠氮基-3'-脱氧胸苷 AZT (1) 的碳环类似物。从对映体纯碳环 2'-脱氧胸苷 2 开始，制备了四种不同的碳环 AZT 类似物 2,4-6。此外，核苷类似物被转化为它们的膜渗透性环磷酸三酯。所有化合物都在体外测试了它们在人 T 淋巴细胞中的抗 HIV 活性 (CEM/0)。(© Wiley-VCH Verlag GmbH & Co. KGaA, 69451 Weinheim, Germany, 2006)