2-N-Acetyl-6-O-((4-nitrophenyl)ethyl)guanosine

• 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-N-Acetyl-6-O-((4-nitrophenyl)ethyl)guanosine
• 英文别名: 2-N-Acetyl-6-O-[(4-nitrophenyl)ethyl]guanosine；N-[9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]-6-[2-(4-nitrophenyl)ethoxy]purin-2-yl]acetamide
• 化学式: C₂₀H₂₂N₆O₈
• 分子量: 474.43
• InChiKey: RTVADISDRCZZNC-NVQRDWNXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  198
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  2-N-Acetyl-6-O-((4-nitrophenyl)ethyl)guanosine 在 吡啶 、 4-二甲氨基吡啶 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 4,4'-二氨基二苯乙烯-2,2'-二磺酸 、 三氟乙酸 作用下， 以 二氯甲烷 、 氯仿 为溶剂， 反应 114.0h， 生成 9-(2-脱氧-2-氟阿拉伯呋喃基)鸟嘌呤
  参考文献：
  名称：

  Nucleosides. 164. Studies directed toward the synthesis of 2'-deoxy-2'-substituted arabino nucleosides. 10. Synthesis of 2'-.beta.-fluoro- and 3'-.alpha.-fluoro-substituted guanine nucleosides. Effect of sugar conformational shifts on nucleophilic displacement of the 2'-hydroxy and 3'-hydroxy group with DAST

  摘要：

  Tritylation of 2-N-acetyl-6-O-((4-nitrophenyl)ethyl)guanosine (4) with TrCl/DMAP followed by TrCl/AgNO3 afforded a mixture of isomeric 3',5'-di-O-trityl and 2',5'-di-O-trityl derivatives 6 and 7, which were separated on a silica gel column to give 6 and 7 in 40% and 50% yield, respectively. Upon treatment with DAST, 6 was converted into the corresponding 2'-beta-fluoro nucleoside 8 in 43% yield. Deprotection of the 2-N-acetyl group occurred during the reaction. Removal of the 6-O-NPE group from 8 with DBU/pyridine, followed by detritylation with CF3COOH/CHCl3, gave F-ara-G (1b) in good yield. The same treatment of 7 with DAST did not lead to nucleophilic substitution with fluoride ion, but only decomposition took place. Treatment of the 2',5'-di-O-trityl nucleoside 7 with CF3SO2Cl/DMAP in CH2Cl2, followed by PhCO2K/HMPA, afforded the corresponding xylofuranosyl derivative 16 along with 6-O-deprotected nucleoside 19. The 6-O-NPE group was completely removed in the reaction of triflate nucleoside 15 with CH3CO2Na/HMPA. The obtained diacetyl nucleoside 20 under hydrolysis with Et3N/MeOH/H2O gave 9-(2,5-di-O-trityl-beta-D-xylofuranosyl)guanine (22). Upon reaction of derivative 22 with DAST no formation of the desired 3'-fluoro nucleoside 23 was observed, but only decomposition took place. When, however, the triflate nucleoside 15 was treated with CH3COONa in DMF instead of HMPA the corresponding diacetyl nucleoside 17 with intact 6-O-NPE group was obtained. This compound was hydrolyzed with Et3N/MeOH/H2O to give the 2-N-acetyl derivative 18, which was smoothly converted into the desired 3'-alpha-fluoro-substituted nucleoside 24 in 76% yield. Again, removal of the 2-N-acetyl group occurred during the reaction with DAST. Compound 24 was deprotected with DBU/pyridine followed by CF3COOH/CHCl3 to give 3'-fluoro-3'-deoxyguanosine in good yield (3b). In a similar manner the O2,O5,N6-tritrityladenosine (25) was converted into the corresponding 3'-deoxy-3'-fluoroadenosine (3a).

  DOI：

  10.1021/jo00052a055
• 作为产物：
  描述：

  (2R,3R,4R,5R)-2-(2-acetamido-6-(4-nitrophenethoxy)-9H-purin-9-yl)-5-(acetoxymethyl)tetrahydrofuran-3,4-diyl diacetate 在 ammonium hydroxide 作用下， 以 水 为溶剂， 生成 2-N-Acetyl-6-O-((4-nitrophenyl)ethyl)guanosine
  参考文献：
  名称：

  [EN] METHODS AND MATERIALS FOR USING [18F]-F-ARAG IN CARDIAC IMAGING
  [FR] MÉTHODES ET MATÉRIAUX POUR L'UTILISATION DE [18F]-F-ARAG DANS L'IMAGERIE CARDIAQUE

  摘要：

  本公开的实施例提供了用于执行正电子发射断层扫描（PET）的组合物和方法，更具体地，提供了用于开发和使用18F基PET示踪剂的组合物和方法，用于选择成像技术，如心肌生理研究。特别地，在示踪剂水平上，[18F]F-AraG具有能够用于许多新的PET方法，包括那些设计用于心脏和/或线粒体活性成像的能力。使用[18F]F-AraG作为PET示踪剂在许多不同应用中比传统的18F标记示踪剂具有显著优势，包括观察选择的生理现象，如心肌灌注、心肌存活和心脏炎症。本发明的方法包括那些旨在使用[18F]F-AraG观察患者对各种治疗剂的生理反应，以及将[18F]F-AraG用作PET示踪剂进行药物开发研究的方法。

  公开号：

  WO2022026533A1

文献信息

• Synthesis of ribonucleoside 3′,5′-cyclic phosphorothioates using a modified hydroxybenzotriazole phosphotriester approach
  作者：E. de Vroom、G. A. van der Marel、J. H. van Boom

  DOI：10.1002/recl.19871061106

  日期：——

  Phosphorothioylation of 3′,5′-dihydroxyl ribonucleosides with O-(2-chlorophenyl) O, O-bis[6-(trifluoromethyl)-1-benzotriazolyl] phosphorothioate, followed by addition of N-methyl-imidazole and removal of protecting groups, gives ribonucleosides 3′,5′-cyclic phosphorothioates. The latter compounds could also be prepared by phosphorothioylation of 2′,3′,5′-trihydroxyl ribonucleosides.

  用O-（2-氯苯基）O，O-双[6-（三氟甲基）-1-苯并三唑基]硫代磷酸酯对3'，5'-二羟基核糖核苷进行硫代磷酸化，然后添加N-甲基-咪唑并除去保护基得到核糖核苷3'，5'-环硫代磷酸酯。后者的化合物也可以通过2'，3'，5'-三羟基核糖核苷的硫代磷酸化来制备。
• COMPOUNDS AND METHODS OF MAKING COMPOUNDS
  申请人：Namavari Mohammad

  公开号：US20110059014A1

  公开（公告）日：2011-03-10

  Embodiments of the present disclosure provide for compounds and methods of making compounds such as those shown in FIGS. 1.1 A and 1.1 B having formula 2, 3, 4, 5, 11, and 12 and formula 2′, 4′, and 11′, as well as uses for the compounds for imaging, and the like.

  本公开说明的实施例提供了化合物及其制备方法，例如图1.1A和1.1B中所示的具有公式2、3、4、5、11和12以及公式2'、4'和11'的化合物，以及化合物用于成像等用途。
• Advances in RNA Labeling with Trifluoromethyl Groups
  作者：Clemens Eichler、Maximilian Himmelstoß、Raphael Plangger、Leonie I. Weber、Markus Hartl、Christoph Kreutz、Ronald Micura

  DOI：10.1002/chem.202302220

  日期：2023.10.26

  the set of 2′-OCF3 nucleoside phosphoramidites to all four standard nucleobases and enables advanced NMR spectroscopic and cellular applications that utilize the favorable properties of the 2′-OCF3 group without any RNA sequence restrictions.

  提出了具有新型氟标记模式的合成 RNA。该研究完善了所有四种标准核碱基的 2′-OCF3 核苷亚磷酰胺组，并实现了先进的 NMR 波谱和细胞应用，这些应用利用了 2′-OCF3 组的有利特性，而不受任何 RNA 序列限制。
• Compounds and Methods of Making Compounds
  申请人：The Board of Trustees of the Leland Stanford Junior University

  公开号：US20150118157A1

  公开（公告）日：2015-04-30

  Embodiments of the present disclosure provide for compounds and methods of making compounds such as those shown in FIGS. 1.1A and 1.1B having formula 2, 3, 4, 5, 11, and 12 and formula 2′, 4′, and 11′,as well as uses for the compounds for imaging, and the like.
• US9011817B2
  申请人：——

  公开号：US9011817B2

  公开（公告）日：2015-04-21