5-formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide | 175545-12-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 咪唑核糖核苷和核糖核苷酸
• 英文名称: 5-formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide
• 英文别名: [(2R,3R,4R,5R)-3,4-diacetyloxy-5-(4-carbamoyl-5-formylimidazol-1-yl)oxolan-2-yl]methyl acetate
• CAS: 175545-12-7
• 化学式: C₁₆H₁₉N₃O₉
• 分子量: 397.342
• InChiKey: XJKDKPXLWBTHHJ-XKVFNRALSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.88
• 重原子数：
  28.0
• 可旋转键数：
  7.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  166.11
• 氢给体数：
  1.0
• 氢受体数：
  11.0

反应信息

• 作为反应物：
  描述：

  5-formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 在 三乙胺 作用下， 以 甲醇 为溶剂， 反应 10.0h， 生成 5-ethynyl-1-β-D-ribofuranosylimidazole-4-carboxamide
  参考文献：
  名称：

  Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-d-Ribofuflranosylimidazole-4-Carboxamides

  摘要：

  Synthesis of 5-carbon-substituted 1-beta-D-ribofuranosylimidazole-4-carboxamides are described. Treatment of 5-iodo derivative 8 with methyl acrylate in the presence of palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl- beta-D-ribofuranosyl)imidazole-4-carboxamide (9), followed by appropriate manipulations to afford various 5-carbon-substituted imidazole derivatives 1-7. The antileukemic activities of these imidazole nucleosides are also described.

  DOI：

  10.1080/07328319608002383
• 作为产物：
  描述：

  methyl (E)-3-[5-carbamoyl-3-[(2R,3R,4R,5R)-3,4-diacetyloxy-5-(acetyloxymethyl)oxolan-2-yl]imidazol-4-yl]prop-2-enoate 在 ozone-containing oxygen 、 二甲基硫 作用下， 生成 5-formyl-1-(2,3,5-tri-O-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide
  参考文献：
  名称：

  Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-d-Ribofuflranosylimidazole-4-Carboxamides

  摘要：

  Synthesis of 5-carbon-substituted 1-beta-D-ribofuranosylimidazole-4-carboxamides are described. Treatment of 5-iodo derivative 8 with methyl acrylate in the presence of palladium catalyst gave (E)-5-(2-carbomethoxyvinyl)-1-(2,3,5-tri-O-acetyl- beta-D-ribofuranosyl)imidazole-4-carboxamide (9), followed by appropriate manipulations to afford various 5-carbon-substituted imidazole derivatives 1-7. The antileukemic activities of these imidazole nucleosides are also described.

  DOI：

  10.1080/07328319608002383