2-amino-6-benzyloxy-9-cyanomethylpurine | 144084-41-3

• 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: 2-amino-6-benzyloxy-9-cyanomethylpurine
• 英文别名: 9H-Purine-9-acetonitrile, 2-amino-6-(phenylmethoxy)-；2-(2-amino-6-phenylmethoxypurin-9-yl)acetonitrile
• CAS: 144084-41-3
• 化学式: C₁₄H₁₂N₆O
• 分子量: 280.289
• InChiKey: UJMYASCLIHSBJU-UHFFFAOYSA-N

物化性质

• 沸点：
  604.4±65.0 °C(Predicted)
• 密度：
  1.41±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.4
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.14
• 拓扑面积：
  103
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  溴乙腈 、 O-6-苄基鸟嘌呤 在 乙醇 、 sodium ethanolate 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 0.5h， 以35%的产率得到2-Amino-6-benzyloxy-7-cyanomethylpurine
  参考文献：
  名称：

  Structural features of substituted purine derivatives compatible with depletion of human O6-alkylguanine-DNA alkyltransferase

  摘要：

  A series of O6- and S6-substituted purine derivatives were tested for their ability to deplete the human DNA repair protein O6-alkylguanine-DNA alkyltransferase (AGT) in cell-free extracts from HT29 colon tumor cells and intact HT29 cells. The order of potency was O6-(p-Y-benzyl)-guanine (Y = H, F, Cl, and CH3) > O6-benzyl-2'-deoxyguanosine > O6-(p-Y-benzyl)guanosine (Y = H, Cl, and CH3) greater-than-or-equal-to a series of 9-substituted O6-benzylguanine derivatives greater-than-or-equal-to O6-allylguanine > O6-benzylhypoxanthine > O6-methylguanine. A series of 7-substituted O6-benzylguanine derivatives, 2-amino-6-(p-Y-benzylthio)purine (Y = H, CH3),2-amino-6-[(p-nitrobenzyl)thiol-9-beta-D-ribofuranosylpurine, and 7-benzylguanine were inactive. It is concluded that for efficient AGT depletion, an allyl or benzyl group attached through exocyclic oxygen at position 6 of a 2-aminopurine derivative is required. Activity is preserved with a variety of substituent groups attached to position 9 while substitution at position 7 leads to a complete loss of activity.

  DOI：

  10.1021/jm00101a028

文献信息

• US5691307A
  申请人：——

  公开号：US5691307A

  公开（公告）日：1997-11-25
• Structural features of substituted purine derivatives compatible with depletion of human O6-alkylguanine-DNA alkyltransferase
  作者：Robert C. Moschel、Mark G. McDougall、M. Eileen Dolan、Linda Stine、Anthony E. Pegg

  DOI：10.1021/jm00101a028

  日期：1992.11

  A series of O6- and S6-substituted purine derivatives were tested for their ability to deplete the human DNA repair protein O6-alkylguanine-DNA alkyltransferase (AGT) in cell-free extracts from HT29 colon tumor cells and intact HT29 cells. The order of potency was O6-(p-Y-benzyl)-guanine (Y = H, F, Cl, and CH3) > O6-benzyl-2'-deoxyguanosine > O6-(p-Y-benzyl)guanosine (Y = H, Cl, and CH3) greater-than-or-equal-to a series of 9-substituted O6-benzylguanine derivatives greater-than-or-equal-to O6-allylguanine > O6-benzylhypoxanthine > O6-methylguanine. A series of 7-substituted O6-benzylguanine derivatives, 2-amino-6-(p-Y-benzylthio)purine (Y = H, CH3),2-amino-6-[(p-nitrobenzyl)thiol-9-beta-D-ribofuranosylpurine, and 7-benzylguanine were inactive. It is concluded that for efficient AGT depletion, an allyl or benzyl group attached through exocyclic oxygen at position 6 of a 2-aminopurine derivative is required. Activity is preserved with a variety of substituent groups attached to position 9 while substitution at position 7 leads to a complete loss of activity.