(2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((3-(trifluoromethyl)benzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol | 23661-03-2

• 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: (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((3-(trifluoromethyl)benzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
• 英文别名: N⁶-(3-trifluoromethylbenzyl)adenosine；N-(3-trifluoromethylbenzyl)adenosine；Antiviral agent 24；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[[3-(trifluoromethyl)phenyl]methylamino]purin-9-yl]oxolane-3,4-diol
• CAS: 23661-03-2
• 化学式: C₁₈H₁₈F₃N₅O₄
• 分子量: 425.367
• InChiKey: SDQKDCSBWUSBDO-LSCFUAHRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  11

反应信息

• 作为反应物：
  描述：

  (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((3-(trifluoromethyl)benzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol 、 二甲基二硫 在 三丁基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以40 %的产率得到(2S,3S,4R,5R)-2-((methylthio)methyl)-5-(6-((3-(trifluoromethyl)benzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  Rational design of novel nucleoside analogues reveals potent antiviral agents for EV71

  摘要：

  DOI：

  10.1016/j.ejmech.2022.114942
• 作为产物：
  描述：

  3-(三氟甲基)苯甲胺 、 6-氯嘌呤核苷 在 N,N-二异丙基乙胺 作用下， 以 正丁醇 为溶剂， 生成 (2R,3S,4R,5R)-2-(hydroxymethyl)-5-(6-((3-(trifluoromethyl)benzyl)amino)-9H-purin-9-yl)tetrahydrofuran-3,4-diol
  参考文献：
  名称：

  通过 Pd 催化的 C-C 键形成延长 N6-苄基腺苷支架，产生具有抗黄病毒活性的衍生物

  摘要：

  用亲脂基团修饰核苷类似物通常会产生具有改善的抗病毒活性的化合物。例如，在苄基核心中含有延长亲脂性取代基的N 6 -苄基腺苷衍生物可有效抑制蜱传脑炎病毒（TBEV）的繁殖，而N 6 -苄基腺苷本身可有效抑制人肠道病毒A71（EV-A71）的繁殖。我们使用C的有效合成方法扩展了一系列N 6 -苄基腺苷类似物 基于 Pd 催化的交叉偶联反应（Sonogashira 和 Suzuki）形成 C 键，以研究腺苷N 6位上大的亲脂性取代基对黄病毒（例如 TBEV、黄热病病毒 (YFV)）的抗病毒活性的影响）和西尼罗河病毒 (WNV)，以及一组肠道病毒，包括 EV-A71、埃可病毒 30 (E30) 和 2 型脊髓灰质炎病毒 (PV2)。所测试的黄病毒的繁殖似乎受到微摩尔浓度的化合物的抑制，而大多数情况下的细胞毒性超出了检测限。添加时间研究表明，命中化合物抑制病毒 RNA 合成阶段，但不抑制病毒进入或蛋

  DOI：

  10.1016/j.bmc.2023.117552

文献信息

• Novel iron complexes bearing N6-substituted adenosine derivatives: Synthesis, magnetic, 57Fe Mössbauer, DFT, and in vitro cytotoxicity studies
  作者：Zdeněk Trávníček、Jiří Mikulík、Michal Čajan、Radek Zbořil、Igor Popa

  DOI：10.1016/j.bmc.2008.07.082

  日期：2008.9

  1H and 13C NMR spectroscopies, magnetochemical and conductivity measurements, thermal (TGA/DSC/DTA) analyses, and DFT calculations. It has been found that the organic molecule is coordinated to iron via N7 atom of the appropriate adenosine derivative and the products are represented by mixtures of complexes with various iron oxidation (Fe(III)/Fe(II)) and spin states (S=5/2, 4/2, 3/2, 2/2) and geometries

  涉及主要成分为[Fe（L（n））Cl（3）]。H（2）O的N6-苄基腺苷衍生物的铁配合物（1-7）其中L（1）= N6-（2-氟苄基）腺苷（1），L（2）= N6-（4-氟苄基）腺苷（2），L（3）= N6-（2-三氟甲基苄基）腺苷（3），L（4）= N6-（3-三氟甲基苄基）腺苷（4），L（5）= N6-（4-三氟甲基苄基）腺苷（5），L（6）= N6-（4-三氟甲氧基苄基）腺苷（6），L（7）= N6-（4-已经合成了氯苄基）腺苷（7）。通过元素分析，可变温度和现场57Fe Mossbauer，ES + MS，FTIR，1H和13C NMR光谱，磁化学和电导率测量，热（TGA / DSC / DTA）分析和DFT计算对化合物进行了表征。已发现有机分子通过适当的腺苷衍生物的N7原子与铁配位，产物由具有各种铁氧化态（Fe（III）/ Fe（II））和自旋态（S = 5 / 2、4 / 2、3
• Substitution derivatives of n6-benzyladenosine, methods of their preparation, their use for preparation of drugs, cosmetic preparations and growth regulators, pharmaceutical preparations, cosmetic preparations and growth regulators containing these compounds
  申请人：Dolezal Karel

  公开号：US20060166925A1

  公开（公告）日：2006-07-27

  The invention concerns novel substitution derivatives of N 6 -benzyladenosine having anticancer, mitotic, immunosuppressive and antisenescent properties for plant, animal and human cells. This invention also relates to the methods of preparation of these N 6 -benzyladenosine derivatives and their use as drugs, cosmetic preparations and growth regulators comprising these derivatives as active compound and use of these derivatives for preparation of pharmaceutical compositions, in biotechnological processes, in cosmetics and in agriculture.

  本发明涉及 N 6 -苄基腺苷的新型取代衍生物，这些衍生物对植物、动物和人体细胞具有抗癌、有丝分裂、免疫抑制和抗增殖特性。本发明还涉及这些 N 6 -苄基腺苷的制备方法。 6 -苄基腺苷衍生物的制备方法，以及它们作为药物、化妆品制剂和生长调节剂的用途，包括这些衍生物作为活性化合物，以及这些衍生物在制备药物组合物、生物技术过程、化妆品和农业中的用途。
• Preparation, biological activity and endogenous occurrence of N6-benzyladenosines
  作者：Karel Doležal、Igor Popa、Eva Hauserová、Lukáš Spíchal、Kuheli Chakrabarty、Ondřej Novák、Vladimír Kryštof、Jiří Voller、Jan Holub、Miroslav Strnad

  DOI：10.1016/j.bmc.2007.03.038

  日期：2007.6

  Cytokinin activity of forty-eight 6-benzyladenosine derivatives at both the receptor and cellular levels as well as their anticancer properties were compared in various in vitro assays. The compounds were prepared by the condensation of 6-chloropurine riboside with corresponding substituted benzylamines and characterized by standard collection of physico-chemical methods. The majority of synthesized derivatives exhibited high activity in all three of the cytokinin bioassays used (tobacco callus, wheat leaf senescence and Amaranthus bioassay). The highest activities were observed in the senescence bioassay. For several of the compounds tested, significant differences in activity were found between the bioassays used, indicating that diverse recognition systems may operate. This suggests that it may be possible to modulate particular cytokinin-dependent processes with specific compounds. In contrast to their high activity in bioassays, the tested compounds were recognized with only very low sensitivity in both Arabidopsis thaliana AHK3 and AHK4 receptor assays. The prepared derivatives were also investigated for their antiproliferative properties on cancer and normal cell lines. Several of them showed very strong cytotoxic activity against various cancer cell lines. On the other hand, they were not cytotoxic for normal murine fibroblast (NIH/3T3) cell line. This anticancer activity of cytokinin ribosides may be important, given that several of them occur as endogenous compounds in different organisms. (c) 2007 Elsevier Ltd. All rights reserved.
• SUBSTITUTION DERIVATIVES OF N SP 6 SP -BENZYLADENOSINE, METHODS OF THEIR PREPARATION, THEIR USE FOR PREPARATION OF DRUGS, COSMETIC PREPARATIONS AND GROWTH REGULATORS, PHARMACEUTICAL PREPARATIONS, COSMETIC PREPARATIONS AND GROWTH REGULATORS CONTAINING THESE COMPOUNDS
  申请人：Ustav Experimentalni Botaniky Akademie ved Ceské Republiky

  公开号：EP1575973A2

  公开（公告）日：2005-09-21
• US8119614B2
  申请人：——

  公开号：US8119614B2

  公开（公告）日：2012-02-21