N-2-methyl-9-<(2-hydroxyethoxy)methyl>guanine | 81475-45-8

• 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: N-2-methyl-9-<(2-hydroxyethoxy)methyl>guanine
• 英文别名: N2-Methylacyclovir；9-(2-hydroxyethoxymethyl)-2-(methylamino)-1H-purin-6-one
• CAS: 81475-45-8
• 化学式: C₉H₁₃N₅O₃
• 分子量: 239.234
• InChiKey: LABRCAXKPIKSKX-UHFFFAOYSA-N

物化性质

• 熔点：
  232-237 °C (decomp)
• 密度：
  1.59±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -1.5
• 重原子数：
  17
• 可旋转键数：
  5
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  101
• 氢给体数：
  3
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  阿昔洛韦 在 ammonium hydroxide 、 N-溴代丁二酰亚胺(NBS) 、 sodium hydride 、 potassium carbonate 作用下， 反应 2.92h， 生成 N-2-methyl-9-<(2-hydroxyethoxy)methyl>guanine
  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：——
• Oligomer-Nitrogenous Base Conjugates
  申请人：Riggs-Sauthier Jennifer

  公开号：US20110059921A1

  公开（公告）日：2011-03-10

  The invention relates to (among other things) oligomer-nitrogenous base conjugates and related compounds. A conjugate of the invention, when administered by any of a number of administration routes, exhibits advantages over unconjugated nitrogenous base compounds.
• 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.