5-amino-1-(β-D-ribofuranosyl)imidazole-4-thiocarboxamide | 19508-94-2

• 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-amino-1-(β-D-ribofuranosyl)imidazole-4-thiocarboxamide
• 英文别名: 5-amino-1-β-D-ribofuranosyl-1H-imidazole-4-carbothioic acid amide；5-Amino-4-thiocarbamoyl-1-β-D-ribofuranosyl-imidazol；5-Amino-4-thiocarbamoyl-1-β-ribofuranosylimidazol；Imidazole-4-carboxamide, 5-amino-1-beta-D-ribofuranosylthio-；5-amino-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]imidazole-4-carbothioamide
• CAS: 19508-94-2
• 化学式: C₉H₁₄N₄O₄S
• 分子量: 274.301
• InChiKey: VZTADWPDAKDQRU-UUOKFMHZSA-N

物化性质

• 沸点：
  725.4±70.0 °C(Predicted)
• 密度：
  2.00±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.6
• 重原子数：
  18
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  172
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为产物：
  描述：

  5-amino-1-β-D-ribofuranosylimidazole-4-carbonitrile 在 硫化氢 、 二乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以88%的产率得到5-amino-1-(β-D-ribofuranosyl)imidazole-4-thiocarboxamide
  参考文献：
  名称：

  Analogs of AICA- and IsoAICA Ribosides and Their Methylated Base Counterparts

  摘要：

  A mild, convenient and efficient synthesis has been developed for imidazole-4-thiocarboxamide and imidazole-5-thiocarboxamide ribosides and the analogous selenocarboxamides. This methodology, i.e., DMF saturated with H2S or H2Se, also converts the corresponding N-methylated bases to the corresponding amides. The imidazole-4(5)-selenocarboxamides were shown to be sensitive to base (pH 11) and were easily converted back to their cyano precursors. The kinetics of these reactions were determined and they indicate that the C5 amides were more reactive than their C4 analogs.

  DOI：

  10.1080/07328319908044611

文献信息

• Analogs of AICA- and <i>Iso</i>AICA Ribosides and Their Methylated Base Counterparts
  作者：Raymond P. Panzica、Leroy B. Townsend

  DOI：10.1080/07328319908044611

  日期：1999.11

  A mild, convenient and efficient synthesis has been developed for imidazole-4-thiocarboxamide and imidazole-5-thiocarboxamide ribosides and the analogous selenocarboxamides. This methodology, i.e., DMF saturated with H2S or H2Se, also converts the corresponding N-methylated bases to the corresponding amides. The imidazole-4(5)-selenocarboxamides were shown to be sensitive to base (pH 11) and were easily converted back to their cyano precursors. The kinetics of these reactions were determined and they indicate that the C5 amides were more reactive than their C4 analogs.