5-amino-3-(O2,O3-isopropylidene-β-D-ribofuranosyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one | 108595-28-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡唑并嘧啶类
• 英文名称: 5-amino-3-(O2,O3-isopropylidene-β-D-ribofuranosyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one
• 英文别名: 2',3'-O-Isopropyliden-8-azaguanosin；5-Amino-3-<2,3-O-isopropyliden-β-D-ribofuranosyl>-3H-v-triazolo<4,5-d>pyrimidin-(7(6)) od. 2',3'-O-Isopropyliden-8-azaguanosin；5-amino-3-(O²,O³-isopropylidene-β-D-ribofuranosyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one；O^2'_,O3'-isopropylidene-8-aza-guanosine
• CAS: 108595-28-4
• 化学式: C₁₂H₁₆N₆O₅
• 分子量: 324.296
• InChiKey: DHUNVZWSJKUTJX-KQYNXXCUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.49
• 重原子数：
  23.0
• 可旋转键数：
  2.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  150.4
• 氢给体数：
  3.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  5-amino-3-(O2,O3-isopropylidene-β-D-ribofuranosyl)-3,6-dihydro-[1,2,3]triazolo[4,5-d]pyrimidin-7-one 在 四氮唑 水 、 溶剂黄146 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 为溶剂， 生成
  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