9-[(2-hydroxyethoxy)methyl]isoguanine

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 9-[(2-hydroxyethoxy)methyl]isoguanine
• 英文别名: Iso-acyclovir；6-amino-9-(2-hydroxyethoxymethyl)-1H-purin-2-one
• 化学式: C₈H₁₁N₅O₃
• 分子量: 225.207
• InChiKey: WLGPYGDPBSTDIX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -2.2
• 重原子数：
  16
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  113
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  5-amino-1-<<2-(acetyloxy)ethoxy>methyl>-1H-imidazole-4-carboxamide 在 ammonium hydroxide 、 N,N'-二环己基碳二亚胺 作用下， 以 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 75.0h， 生成 9-[(2-hydroxyethoxy)methyl]isoguanine
  参考文献：
  名称：

  5-Cyanoamino-4-imidazolecarboxamide and Nitrosative Guanine Deamination:  Experimental Evidence for Pyrimidine Ring-Opening during Deamination

  摘要：

  5-Cyanoamino-4-imidazolecarboxamide 4a (R = CH2-O-CH2-CH2-OH) has been synthesized, purified, and fully characterized by MS, MS/MS, HRMS, IR spectroscopy, and by 1H and 13C NMR spectroscopy. It is shown that cyclization of 4a yields the guanine 6a and the isoguanine 12a. Our findings provide experimental evidence in support of our hypothesis that the formation of oxanine and xanthine in nitrosative guanine deamination may proceed via pyrimidine ring-opened intermediates. The observed formation of 6a from the amide 4a (XH2 = NH2) shows that, in analogy, oxanine can be formed from 3 (XH = OH). The formation of 12a from 4a reveals for the first time the possibility that oxanine might be formed by a second pathway that involves electrocyclic reaction of 3. Finally, the new chemistry suggests the possibility for a new dG-to-dG cross-link.

  DOI：

  10.1021/ja0389523

文献信息

• 5-Cyanoamino-4-imidazolecarboxamide and Nitrosative Guanine Deamination:  Experimental Evidence for Pyrimidine Ring-Opening during Deamination
  作者：Ming Qian、Rainer Glaser

  DOI：10.1021/ja0389523

  日期：2004.3.3

  5-Cyanoamino-4-imidazolecarboxamide 4a (R = CH2-O-CH2-CH2-OH) has been synthesized, purified, and fully characterized by MS, MS/MS, HRMS, IR spectroscopy, and by 1H and 13C NMR spectroscopy. It is shown that cyclization of 4a yields the guanine 6a and the isoguanine 12a. Our findings provide experimental evidence in support of our hypothesis that the formation of oxanine and xanthine in nitrosative guanine deamination may proceed via pyrimidine ring-opened intermediates. The observed formation of 6a from the amide 4a (XH2 = NH2) shows that, in analogy, oxanine can be formed from 3 (XH = OH). The formation of 12a from 4a reveals for the first time the possibility that oxanine might be formed by a second pathway that involves electrocyclic reaction of 3. Finally, the new chemistry suggests the possibility for a new dG-to-dG cross-link.