5-hydroxymethyl-1-β-D-ribofuranosylimidazole-4-carboxamide | 114484-98-9

• 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-hydroxymethyl-1-β-D-ribofuranosylimidazole-4-carboxamide
• 英文别名: 1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-5-(hydroxymethyl)imidazole-4-carboxamide
• CAS: 114484-98-9
• 化学式: C₁₀H₁₅N₃O₆
• 分子量: 273.246
• InChiKey: TVNJLRAHGSGUPT-VPCXQMTMSA-N

物化性质

• 沸点：
  757.9±60.0 °C(predicted)
• 密度：
  1.92±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3.2
• 重原子数：
  19
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  151
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-iodo-1-(2,3,5-tri-0-acetyl-β-D-ribofuranosyl)imidazole-4-carboxamide 在 ozone-containing oxygen 、 二(氰基苯)二氯化钯 、 氨 、 sodium cyanoborohydride 、 三乙胺 作用下， 以 甲醇 、 乙腈 为溶剂， 反应 18.25h， 生成 5-hydroxymethyl-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

文献信息

• Synthesis of 5-carbon-substituted 1-.BETA.-D-ribofuranosylimidazole-4-carboxamides via lithiation of a primary carboxamide.
  作者：MASAHIRO SUZUKI、HIROMICHI TANAKA、TADASHI MIYASAKA

  DOI：10.1248/cpb.35.4056

  日期：——

  Several 5-carbon-substituted 1-β-D-ribofuranosylimidazole-4-carboxamides were synthesized via the direct C-5 lithiation of a protected 4-carboxamide derivative as the key reaction step. Wittig reaction of a 5-formyl derivative was also examined.

  以受保护的 4-甲酰胺衍生物的直接 C-5 锂化反应为关键步骤，合成了几种 5 碳取代的 1-β-D-ribofuranosylimidazole-4- Carboxamides。还研究了 5-甲酰基衍生物的 Wittig 反应。
• SUZUKI, MASAHIRO;TANAKA, HIROMICHI;MIYASAKA, TADASHI, CHEM. AND PHARM. BULL., 35,(1987) N 10, 4056-4063
  作者：SUZUKI, MASAHIRO、TANAKA, HIROMICHI、MIYASAKA, TADASHI

  DOI：——

  日期：——
• Nucleosides and Nucleotides. 140. Synthesis and Antileukemic Activity of 5-Carbon-Substituted 1-β-<scp>d</scp>-Ribofuflranosylimidazole-4-Carboxamides
  作者：Noriaki Minakawa、Naoshi Kojima、Takuma Sasaki、Akira Matsuda

  DOI：10.1080/07328319608002383

  日期：1996.1

  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.