O⁶-benzyl-9-methylguanine | 152833-01-7

• 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-9-methylguanine
• 英文别名: 6-O-benzyl-9-methyl-guanine；9-Methyl-6-phenylmethoxypurin-2-amine
• CAS: 152833-01-7
• 化学式: C₁₃H₁₃N₅O
• 分子量: 255.279
• InChiKey: NTJHRKCJHIPHBB-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

• 作为反应物：
  描述：

  O⁶-benzyl-9-methylguanine 在 polymeric BEMP 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 生成 2-Methoxy-N-(9-methyl-6-oxo-6,9-dihydro-1H-purin-2-yl)-acetamide
  参考文献：
  名称：

  Convenient synthesis of 2,9-disubstituted guanines mediated by solid-supported reagents

  摘要：

  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.

  DOI：

  10.1016/s0040-4039(00)00466-4
• 作为产物：
  描述：

  6-氯-9-甲基-9H-嘌呤-2-胺 、 苯甲醇 在 sodium 作用下， 反应 49.0h， 以26%的产率得到O⁶-benzyl-9-methylguanine
  参考文献：
  名称：

  Universal Base

  摘要：

  本发明提供了一种人工通用碱基，能够非特异性地与四种天然核酸碱基（A、T、G 和 C）中的任何一种进行碱基配对，而无需特异性识别配对天然核酸碱基以进行碱基配对形成。具有非特异性地与四种天然核酸碱基进行碱基配对的通用碱基，其中通用碱基具有以下化学式所代表的结构：其中 R 代表除氢原子以外的一价基团。

  公开号：

  US20100036108A1

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.
• US8211899B2
  申请人：——

  公开号：US8211899B2

  公开（公告）日：2012-07-03
• Universal Base
  申请人：Kataoka Masanori

  公开号：US20100036108A1

  公开（公告）日：2010-02-11

  The present invention provides artificial universal base capable of base pairing nonspecifically with any of four kinds of natural nucleic acid bases (A, T, G, and C) without the function to specifically recognize pairing natural nucleic acid bases for base pair formation. Universal base capable of base paring nonspecifically with four kinds of natural nucleic acid bases, wherein the universal base has a structure represented by the following chemical formula: wherein R represents a monovalent group other than a hydrogen atom.

  本发明提供了一种人工通用碱基，能够非特异性地与四种天然核酸碱基（A、T、G 和 C）中的任何一种进行碱基配对，而无需特异性识别配对天然核酸碱基以进行碱基配对形成。具有非特异性地与四种天然核酸碱基进行碱基配对的通用碱基，其中通用碱基具有以下化学式所代表的结构：其中 R 代表除氢原子以外的一价基团。
• 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.