2-amino-5-ethyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one | 129872-87-3

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并吡啶类
• 英文名称: 2-amino-5-ethyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one
• 英文别名: 2-amino-5-ethyl-3H-pyrrolo[3,2-d]pyrimidin-4-one
• CAS: 129872-87-3
• 化学式: C₈H₁₀N₄O
• 分子量: 178.194
• InChiKey: YNLZOJJSWMGWKX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.5
• 重原子数：
  13
• 可旋转键数：
  1
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.25
• 拓扑面积：
  72.4
• 氢给体数：
  2
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  2-amino-5-ethyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one 在 sodium methylate 、 四氯化锡 作用下， 以 甲醇 、 硝基甲烷 为溶剂， 反应 3.0h， 生成 2-amino-5-ethyl-7-β-D-ribofuranosyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one
  参考文献：
  名称：

  Direct C-glycosylation of guanine analogs: the synthesis and antiviral activity of certain 7- and 9-deazaguanine C-nucleosides

  摘要：

  C-Glycosylation of two guanine analogues, 9-deaza- and 7-deazaguanine, has been achieved under Friedel-Crafts conditions, providing a direct synthetic route to 9-deazaguanosine (4; 2-amino-7-beta-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one) and 8-beta-D-ribofuranosyl-7-deazaguanine (16), respectively. This electrophilic C-glycosylation was applied successfully to six guanine and substituted-guanine analogues resulting in yields of approximately 50%. This represents the first reported C-ribosylation of preformed nitrogen heterocycles isosteric with guanine. These C-nucleosides were evaluated for their ability to provide protection against a lethal Semliki Forest virus infection in mice, relative to 7-thia-8-oxoguanosine which was used as a positive control. Two of the C-nucleosides, 2-amino-6-chloro-5-methyl-7-beta-D-ribofuranosyl-5H-pyrrolo [3,2-d]pyrimidin-4(3H)-one (12) and the corresponding 6-bromo derivative (13), showed good prophylactic activity in this virus model system.

  DOI：

  10.1021/jm00172a011
• 作为产物：
  描述：

  2-chloro-5-ethyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one 在 氨 作用下， 以 甲醇 为溶剂， 反应 12.0h， 以78%的产率得到2-amino-5-ethyl-5H-pyrrolo<3,2-d>pyrimidin-4(3H)-one
  参考文献：
  名称：

  Direct C-glycosylation of guanine analogs: the synthesis and antiviral activity of certain 7- and 9-deazaguanine C-nucleosides

  摘要：

  C-Glycosylation of two guanine analogues, 9-deaza- and 7-deazaguanine, has been achieved under Friedel-Crafts conditions, providing a direct synthetic route to 9-deazaguanosine (4; 2-amino-7-beta-D-ribofuranosyl-5H-pyrrolo[3,2-d]pyrimidin-4(3H)-one) and 8-beta-D-ribofuranosyl-7-deazaguanine (16), respectively. This electrophilic C-glycosylation was applied successfully to six guanine and substituted-guanine analogues resulting in yields of approximately 50%. This represents the first reported C-ribosylation of preformed nitrogen heterocycles isosteric with guanine. These C-nucleosides were evaluated for their ability to provide protection against a lethal Semliki Forest virus infection in mice, relative to 7-thia-8-oxoguanosine which was used as a positive control. Two of the C-nucleosides, 2-amino-6-chloro-5-methyl-7-beta-D-ribofuranosyl-5H-pyrrolo [3,2-d]pyrimidin-4(3H)-one (12) and the corresponding 6-bromo derivative (13), showed good prophylactic activity in this virus model system.

  DOI：

  10.1021/jm00172a011

文献信息

• GIRGIS, NABIH S.;MICHAEL, MAGED A.;SMEE, DONALD F.;ALAGHAMANDAN, HASSAN A+, J. MED. CHEM., 33,(1990) N0, C. 2750-2755
  作者：GIRGIS, NABIH S.、MICHAEL, MAGED A.、SMEE, DONALD F.、ALAGHAMANDAN, HASSAN A+

  DOI：——

  日期：——