5-(5-amino-4-carbamoylimidazol-1-yl)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose | 183194-56-1

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 5-(5-amino-4-carbamoylimidazol-1-yl)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
• 英文别名: 1-[[(3aR,5R,6S,6aR)-6-hydroxy-2,2-dimethyl-3a,5,6,6a-tetrahydrofuro[2,3-d][1,3]dioxol-5-yl]methyl]-5-aminoimidazole-4-carboxamide
• CAS: 183194-56-1
• 化学式: C₁₂H₁₈N₄O₅
• 分子量: 298.299
• InChiKey: ZWJKPQMZRLJKGH-GZCUOZMLSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  135
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  5-(5-amino-4-carbamoylimidazol-1-yl)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 acid 作用下， 生成 1,5'-cyclo-5-(5'-deoxy-β-D-xylofuranosylamino)imidazol-4-carboxamide
  参考文献：
  名称：

  Chabbi, M.; Vanlemmens, P.; Ronco, G., Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S12 - S15

  摘要：

  DOI：
• 作为产物：
  描述：

  5-azido-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose 在 三苯基膦 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 16.75h， 生成 5-(5-amino-4-carbamoylimidazol-1-yl)-5-deoxy-1,2-O-isopropylidene-α-D-xylofuranose
  参考文献：
  名称：

  Entry to the 2,5-Epoxyimidazo[1,5-a][1,3]Diazocine and 5,8-Epoxy[1,2,3]Triazolo[1,5-a][1,3]Diazocine Systems : Novel Reversed Cyclonucleoside Analogues

  摘要：

  5-Azido-5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose was used to obtain two reversed nucleoside analogues with either the 5-aminoimidazol-4-carboxamide or 5-amino-1,2,3-triazol-4-carboxamide groups attached, through the N1 site, to the C5' site of the sugar. When deprotected these two compounds cyclised spontaneously and regiospecifically to form a bond between the exocyclic nitrogen and the anomeric carbon of the sugar. These reversed cyclonucleoside analogues are respectively members of the 2,5-epoxyimidazo[1,5-a][1,3]diazocine and 5,8-epoxy[1,2,3]triazolo[1,5-a][1,3]diazocine systems, novel ring systems with therapeutic potential. The shape of the cyclised imidazole compound and its immediate precursor has been studied by molecular modelling.

  DOI：

  10.1080/07328309908544008

文献信息

• Chabbi, M.; Vanlemmens, P.; Ronco, G., Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S12 - S15
  作者：Chabbi, M.、Vanlemmens, P.、Ronco, G.、Goethals, G.、Villa, P.、et al.

  DOI：——

  日期：——
• Entry to the 2,5-Epoxyimidazo[1,5-<i>a</i>][1,3]Diazocine and 5,8-Epoxy[1,2,3]Triazolo[1,5-<i>a</i>][1,3]Diazocine Systems : Novel Reversed Cyclonucleoside Analogues
  作者：D.F. Ewing、G. Goethals、G. Mackenzie、P. Martin、G. Ronco、L. Vanbaelinghem、P. Villa

  DOI：10.1080/07328309908544008

  日期：1999.1

  5-Azido-5-deoxy-1,2-O-isopropylidene-alpha-D-xylofuranose was used to obtain two reversed nucleoside analogues with either the 5-aminoimidazol-4-carboxamide or 5-amino-1,2,3-triazol-4-carboxamide groups attached, through the N1 site, to the C5' site of the sugar. When deprotected these two compounds cyclised spontaneously and regiospecifically to form a bond between the exocyclic nitrogen and the anomeric carbon of the sugar. These reversed cyclonucleoside analogues are respectively members of the 2,5-epoxyimidazo[1,5-a][1,3]diazocine and 5,8-epoxy[1,2,3]triazolo[1,5-a][1,3]diazocine systems, novel ring systems with therapeutic potential. The shape of the cyclised imidazole compound and its immediate precursor has been studied by molecular modelling.