2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolyl-1,9-dihydro-purin-6-one | 79953-04-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolyl-1,9-dihydro-purin-6-one
• 英文别名: Guanosine, 8-(4-methylphenyl)-；2-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-8-(4-methylphenyl)-1H-purin-6-one
• CAS: 79953-04-1
• 化学式: C₁₇H₁₉N₅O₅
• 分子量: 373.368
• InChiKey: RVLWIFCKXLFCBB-UBEDBUPSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.1
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  155
• 氢给体数：
  5
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolyl-1,9-dihydro-purin-6-one 在 盐酸 作用下， 反应 1.0h， 以100%的产率得到2-Amino-8-p-tolyl-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Reactions of benzenediazonium ions with guanine and its derivatives

  摘要：

  DOI：

  10.1021/jo00342a014
• 作为产物：
  描述：

  p-toluenediazonium hydrogen sulfate 、 鸟苷 在 sodium hydroxide 作用下， 反应 24.0h， 生成 2-Amino-9-((2R,3R,4S,5R)-3,4-dihydroxy-5-hydroxymethyl-tetrahydro-furan-2-yl)-8-p-tolyl-1,9-dihydro-purin-6-one
  参考文献：
  名称：

  Different Patterns of Mutagenicity of Arenediazonium Ions in V79 Cells and Salmonella typhimurium TA102: Evidence for Different Mechanisms of Action

  摘要：

  The edible mushroom Agaricus bisporus contains several arylhydrazines and arenediazonium ions that are genotoxins. The mechanism whereby arylhydrazines and arenediazonium ions are genotoxic is unknown and may be due to the arenediazonium ion itself or to aryl radicals. The reactions of four arenediazonium ions (p-X-C6H5N2+, X = -CH3, -CH2OH, -CH2OCH3, -CO2H) with purine bases, their mutagenicity, their ability to cause DNA damage, and their tendency toward free radical formation have been studied to elucidate the genotoxic species. It is suggested that either the arenediazonium or aryl radical can act as the ultimate genotoxin. Which species is dominant is dependent upon the arenediazonium ion reduction potential. This relationship may be useful in designing future studies of arenediazonium ion genotoxicity.

  DOI：

  10.1021/jf00058a014

文献信息

• Suzuki–Miyaura Cross‐Coupling of Unprotected Halopurine Nucleosides in Water—Influence of Catalyst and Cosolvent
  作者：Alice Collier、Gerd K. Wagner

  DOI：10.1080/10916460600946139

  日期：2006.12

  Abstract Reaction conditions for the Suzuki–Miyaura cross‐coupling of unprotected halopurine nucleosides with arylboronic acids in aqueous media were investigated. A series of arylated purine nucleosides was prepared in water without an organic cosolvent, using either Pd(PPh3)4 or Pd(OAc)2/TPPTS as the catalyst.

  摘要 研究了水介质中未保护的卤代嘌呤核苷与芳基硼酸的 Suzuki-Miyaura 交叉偶联反应条件。在没有有机助溶剂的情况下，使用 Pd(PPh3)4 或 Pd(OAc)2/TPPTS 作为催化剂，在水中制备了一系列芳基化嘌呤核苷。
• A facile two-step synthesis of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs)
  作者：Alice Collier、Gerd Wagner

  DOI：10.1039/b614477b

  日期：——

  We report a simple and high-yielding two-step procedure for the preparation of 8-arylated guanosine mono- and triphosphates (8-aryl GXPs). The key step of our synthesis is the Suzuki–Miyaura coupling of unprotected 8-bromo GMP and 8-bromo GTP with various arylboronic acids in aqueous solution. The 8-bromoguanosine 5′-phosphates required as cross-coupling substrates were prepared from 8-bromoguanosine via an optimised Yoshikawa procedure.

  我们报告了一种简单而高产的两步法制备 8-芳基鸟苷酸单磷酸和三磷酸酯（8-芳基 GXP）。我们合成的关键步骤是在水溶液中将未受保护的 8-溴 GMP 和 8-溴 GTP 与各种芳基硼酸进行铃木-宫脲偶联。作为交叉耦合底物所需的 8-溴鸟苷 5′-磷酸酯是通过优化吉川程序从 8-溴鸟苷制备的。