7-methyl-9-<(2-hydroxyethoxy)methyl>-1,N-2-isopropenoguanine | 114199-21-2

• 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: 7-methyl-9-<(2-hydroxyethoxy)methyl>-1,N-2-isopropenoguanine
• 英文别名: 7-methyl-9-[(2-hydroxyethoxy)methyl]-1,N-2-isopropenoguanine；7-Methyl-1,N2-isopropenoacyclovir；3-(2-hydroxyethoxymethyl)-1,6-dimethylimidazo[1,2-a]purin-3-ium-9-olate
• CAS: 114199-21-2
• 化学式: C₁₂H₁₅N₅O₃
• 分子量: 277.283
• InChiKey: CYOYUUNJZWQANX-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  20
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  91.5
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  阿昔洛韦 在 ammonium hydroxide 、 sodium hydride 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 30.75h， 生成 7-methyl-9-<(2-hydroxyethoxy)methyl>-1,N-2-isopropenoguanine
  参考文献：
  名称：

  Synthesis and antiviral activity of novel N-substituted derivatives of acyclovir

  摘要：

  Novel N-substituted derivatives of acyclovir (1a) were synthesized and evaluated for their antiviral, antimetabolic, and antitumor cell properties in vitro. Monomethylation of 1a at positions 1, 7, and N-2 gave compounds 2-4, respectively. When positions 1 and N-2 were linked together by an isopropeno group, the tricyclic 9-[(2-hydroxyethoxy)methyl]-1,N-2-isopropenoguanine (5) was obtained. Compound 5 was then further methylated at positions N-2 and 7 to give 6 and 7, respectively. None of the new acyclovir derivatives showed any appreciable antimetabolic or antitumor cell activity. However, compounds 2 and 5 exhibited a marked antiherpetic activity. Their activity spectrum was similar to that of acyclovir, and their selectivity as inhibitors of herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) was at least as great as, if not greater than, that of acyclovir.

  DOI：

  10.1021/jm00402a017

文献信息

• BORYSKI, JERZY;GOLANKIEWICZ, BOZENNA;DE, CLERCQ ERIK, J. MED. CHEM., 31,(1988) N 7, C. 1351-1355
  作者：BORYSKI, JERZY、GOLANKIEWICZ, BOZENNA、DE, CLERCQ ERIK

  DOI：——

  日期：——
• Synthesis and antiviral activity of novel N-substituted derivatives of acyclovir
  作者：Jerzy Boryski、Bozenna Golankiewicz、Erik De Clercq

  DOI：10.1021/jm00402a017

  日期：1988.7

  Novel N-substituted derivatives of acyclovir (1a) were synthesized and evaluated for their antiviral, antimetabolic, and antitumor cell properties in vitro. Monomethylation of 1a at positions 1, 7, and N-2 gave compounds 2-4, respectively. When positions 1 and N-2 were linked together by an isopropeno group, the tricyclic 9-[(2-hydroxyethoxy)methyl]-1,N-2-isopropenoguanine (5) was obtained. Compound 5 was then further methylated at positions N-2 and 7 to give 6 and 7, respectively. None of the new acyclovir derivatives showed any appreciable antimetabolic or antitumor cell activity. However, compounds 2 and 5 exhibited a marked antiherpetic activity. Their activity spectrum was similar to that of acyclovir, and their selectivity as inhibitors of herpes simplex virus type 1 (HSV-1) and type 2 (HSV-2) was at least as great as, if not greater than, that of acyclovir.