5-[(cyclohexylamino)methyleneamino]-1-(β-D-ribofuranosyl)imidazole-4-[N-(2,4-dinitrophenyl)]carboxamide | 1042101-26-7

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 5-[(cyclohexylamino)methyleneamino]-1-(β-D-ribofuranosyl)imidazole-4-[N-(2,4-dinitrophenyl)]carboxamide
• 英文别名: 5-(cyclohexyliminomethylamino)-1-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-N-(2,4-dinitrophenyl)imidazole-4-carboxamide
• CAS: 1042101-26-7
• 化学式: C₂₂H₂₇N₇O₉
• 分子量: 533.498
• InChiKey: VEJFSCFGYOJPJI-WGQQHEPDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  38
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  233
• 氢给体数：
  5
• 氢受体数：
  11

反应信息

• 作为产物：
  描述：

  1-(2,4-dinitrophenyl)inosine 、 环己胺 在 吡啶 、 4-二甲氨基吡啶 、 三氟乙酸 作用下， 以 N,N-二甲基甲酰胺 、 二氯甲烷 为溶剂， 反应 32.13h， 生成 5-[(cyclohexylamino)methyleneamino]-1-(β-D-ribofuranosyl)imidazole-4-[N-(2,4-dinitrophenyl)]carboxamide
  参考文献：
  名称：

  Synthesis of 4-N-alkyl and ribose-modified AICAR analogues on solid support

  摘要：

  Herein, we report the solid-phase synthesis of several 5-aminoimidazole-4-(N-alkyl)carboxamide-1-ribosides (4-N-alkyl AICARs) and the corresponding 2',3'-secoriboside derivatives. The method uses the N-1-dinitrophenyl-inosine 5'-bonded to a solid support. This inosine derivative has the C-2 of the purine base strongly activated towards the attack of N-nucleophiles thus allowing the preparation of several N-1 alkylated inosine supports from which a small library of 4-N-alkyl AICAR derivatives has been synthesized. A set of new 4-N-alkyl AICA-2',3'-secoriboside derivatives have also been obtained in high yields by solid-phase cleavage of the 2',3'-ribose bond. (c) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2008.04.071