O⁶-benzyl-7-methylguanine

• 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: O⁶-benzyl-7-methylguanine
• 英文别名: 7-Methyl-6-phenylmethoxypurin-2-amine
• 化学式: C₁₃H₁₃N₅O
• 分子量: 255.279
• InChiKey: QWBWFRAEWXREID-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.5
• 重原子数：
  19
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.15
• 拓扑面积：
  78.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  O-6-苄基鸟嘌呤 、 碘甲烷 在 sodium ethanolate 作用下， 生成 O⁶-benzyl-9-methylguanine 、 O⁶-benzyl-7-methylguanine
  参考文献：
  名称：

  Substituted O6-Benzylguanine Derivatives and Their Inactivation of Human O6-Alkylguanine-DNA Alkyltransferase

  摘要：

  Several new O-6-benzylguanine analogs bearing increasingly bulky substituent groups on the benzene ring or at position 9 were tested for their ability to inactivate the human DNA repair protein, O-6-alkylguanine-DNA alkyltransferase. Substitution on the benzene ring was well tolerated although activity varied considerably with structural changes in groups attached to position 9. For this site, activity was preserved with large or small lipophilic groups while introduction of non-carbohydrate polar groups generally reduced activity regardless of their size.

  DOI：

  10.1021/jm00029a005

文献信息

• Substituted O6-Benzylguanine Derivatives and Their Inactivation of Human O6-Alkylguanine-DNA Alkyltransferase
  作者：Mi Young Chae、Mark G. McDougall、M. Eileen Dolan、Kristin Swenn、Anthony E. Pegg、Robert C. Moschel

  DOI：10.1021/jm00029a005

  日期：1994.2

  Several new O-6-benzylguanine analogs bearing increasingly bulky substituent groups on the benzene ring or at position 9 were tested for their ability to inactivate the human DNA repair protein, O-6-alkylguanine-DNA alkyltransferase. Substitution on the benzene ring was well tolerated although activity varied considerably with structural changes in groups attached to position 9. For this site, activity was preserved with large or small lipophilic groups while introduction of non-carbohydrate polar groups generally reduced activity regardless of their size.
• Convenient synthesis of 2,9-disubstituted guanines mediated by solid-supported reagents
  作者：Warren McComas、Li Chen、Kyungjin Kim

  DOI：10.1016/s0040-4039(00)00466-4

  日期：2000.5

  A novel application has been developed to separate regioisomers chemoselectively using a solid-supported reagent. An N7/N9 purine regioisomer mixture was purified using aluminum oxide/H+ to provide the N9 isomer selectively as a parallel or high-throughput format (chemoselective high-throughput purification). 2,9-Disubstituted guanines were conveniently prepared by this new method in conjunction with solid-supported reagents. (C) 2000 Elsevier Science Ltd. All rights reserved.