5-amino-1-[1-(1,3-dihydroxypropan-2-yloxy)-2-hydroxyethyl]imidazole-4-[N-(5-hydroxypentyl)]carboxamide | 1042100-98-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 唑类
• 英文名称: 5-amino-1-[1-(1,3-dihydroxypropan-2-yloxy)-2-hydroxyethyl]imidazole-4-[N-(5-hydroxypentyl)]carboxamide
• CAS: 1042100-98-0
• 化学式: C₁₄H₂₆N₄O₆
• 分子量: 346.384
• InChiKey: PEQUNOFXLMKNHN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -1.78
• 重原子数：
  24.0
• 可旋转键数：
  12.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.71
• 拓扑面积：
  163.09
• 氢给体数：
  6.0
• 氢受体数：
  9.0

反应信息

• 作为产物：
  描述：

  1-(2,4-dinitrophenyl)inosine 、 5-氨基-1-戊醇 生成 5-amino-1-[1-(1,3-dihydroxypropan-2-yloxy)-2-hydroxyethyl]imidazole-4-[N-(5-hydroxypentyl)]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