5-amino-1-<2,3-O-isopropylidene-5-(2-tetrahydropyranyl)-β-D-ribofuranosyl>-4-<4-(ethoxycarbonyl)pyrazol-3-yl>imidazole | 139574-47-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-<2,3-O-isopropylidene-5-(2-tetrahydropyranyl)-β-D-ribofuranosyl>-4-<4-(ethoxycarbonyl)pyrazol-3-yl>imidazole
• 英文别名: ethyl 5-[1-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(oxan-2-yloxymethyl)-3a,4,6,6a-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl]-5-aminoimidazol-4-yl]-1H-pyrazole-4-carboxylate
• CAS: 139574-47-3
• 化学式: C₂₂H₃₁N₅O₇
• 分子量: 477.517
• InChiKey: JSJCCBRKFCGKCF-RROXPFKFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  145
• 氢给体数：
  2
• 氢受体数：
  10

反应信息

• 作为反应物：
  描述：

  5-amino-1-<2,3-O-isopropylidene-5-(2-tetrahydropyranyl)-β-D-ribofuranosyl>-4-<4-(ethoxycarbonyl)pyrazol-3-yl>imidazole 在 potassium phosphate buffer 、 氨 、 溴 、 碳酸氢钠 作用下， 以 甲醇 、 乙酸乙酯 为溶剂， 反应 100.5h， 生成 9-Bromo-3-[(3aR,4R,6R,6aR)-2,2-dimethyl-6-(tetrahydro-pyran-2-yloxymethyl)-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-3H-pyrazolo[5,1-i]purine
  参考文献：
  名称：

  Design and Synthesis of a New Fluorescent Tricyclic Nucleoside, 3-.beta.-D-Ribofuranosylpyrazolo[3,2-i]purine

  摘要：

  The novel nucleoside, 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine, has been prepared in seven steps from a fully protected 6-chloropurine derivative including a one-step reaction for the preparation of an ethyl 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine derivative from 6-enamino purine and hydrazine. The mechanism for the preparation of 9-ethyl-substituted pyrazolo[3,2-i]purines was elucidated. First, the hydrazino moiety of 6-enamino purine attacks at the C-6 carbon of the purine ring to give a spiro intermediate; this is followed by ring opening and cyclization. The new tricyclic nucleoside exhibited stronger fluorescence than that of 1,N6-ethenoadenosine. Also, the compound and the 9-bromo-substituted pyrazolo[3,2-i]purine nucleoside showed cytotoxic activities against human leukemia CCRF-HSB-2 cells in culture.

  DOI：

  10.1021/jo00085a046
• 作为产物：
  描述：

  ethyl 3-<2,3-O-isopropylidene-5-O-(2-tetrahydropyranyl)-β-D-ribofuranosyl>pyrazolo<3,2-i>purine-9-carboxylate 在 sodium hydroxide 作用下， 反应 20.0h， 以32%的产率得到5-amino-1-<2,3-O-isopropylidene-5-(2-tetrahydropyranyl)-β-D-ribofuranosyl>-4-<4-(ethoxycarbonyl)pyrazol-3-yl>imidazole
  参考文献：
  名称：

  Design and Synthesis of a New Fluorescent Tricyclic Nucleoside, 3-.beta.-D-Ribofuranosylpyrazolo[3,2-i]purine

  摘要：

  The novel nucleoside, 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine, has been prepared in seven steps from a fully protected 6-chloropurine derivative including a one-step reaction for the preparation of an ethyl 3-beta-D-ribofuranosylpyrazolo[3,2-i]purine derivative from 6-enamino purine and hydrazine. The mechanism for the preparation of 9-ethyl-substituted pyrazolo[3,2-i]purines was elucidated. First, the hydrazino moiety of 6-enamino purine attacks at the C-6 carbon of the purine ring to give a spiro intermediate; this is followed by ring opening and cyclization. The new tricyclic nucleoside exhibited stronger fluorescence than that of 1,N6-ethenoadenosine. Also, the compound and the 9-bromo-substituted pyrazolo[3,2-i]purine nucleoside showed cytotoxic activities against human leukemia CCRF-HSB-2 cells in culture.

  DOI：

  10.1021/jo00085a046