9-(2-deoxy-4-thio-α-D-ribofuranosyl)-6-aminopurine | 221286-59-5

• 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: 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-6-aminopurine
• 英文别名: (2R,3S,5S)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)tetrahydrothiophen-3-ol；(2R,3S,5S)-5-(6-aminopurin-9-yl)-2-(hydroxymethyl)thiolan-3-ol
• CAS: 221286-59-5
• 化学式: C₁₀H₁₃N₅O₂S
• 分子量: 267.312
• InChiKey: KSPWPIFRZGARDG-XVMARJQXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  ((hydroxyphosphoryl)bis(oxy))bis(methylene) bis(2,2-dimethylpropanoate) 、 9-(2-deoxy-4-thio-α-D-ribofuranosyl)-6-aminopurine 在 三苯基膦 、 偶氮二甲酸二乙酯 作用下， 以 N,N-二甲基乙酰胺 为溶剂， 以28%的产率得到
  参考文献：
  名称：

  bis(tBuSATE) PHOSPHOTRIESTER PRODRUGS OF 8-AZAGUANOSINE AND 6-METHYLPURINE RIBOSIDE; bis(POM) PHOSPHOTRIESTER PRODRUGS OF 2′-DEOXY-4′-THIOADENOSINE AND ITS CORRESPONDING 9α ANOMER

  摘要：

  As an extension of previous work with bis(POM) nucleotide prodrugs, we report the synthesis and biological evaluation in tumor cell culture of the bis(pivaloyloxymethyl) phosphatriester prodrug of slightly cytotoxic 2'-deoxy-4'-thioadenosine and its alpha-anomer. We have experienced need for an alternative phosphate masking group, particularly with purine nucleosides. Accordingly, we report synthesis and biological evaluation of the bis(tBuSATE)phosphotriester prodrugs of 8-azaguanosine and 6-methylpurine riboside, nucleoside analogs with moderate to significant cytotoxicity. All four prodrugs were examined in tumor cell culture in parallel with the parent nucleosides. Synthetic routes and biological data are presented.

  DOI：

  10.1081/ncn-200061889

文献信息

• US5591722A
  申请人：——

  公开号：US5591722A

  公开（公告）日：1997-01-07