(-)-N⁶-(benzyl)-2'-deoxyadenosine | 37113-47-6

• 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: (-)-N⁶-(benzyl)-2'-deoxyadenosine
• 英文别名: N⁶-(benzyl)-2'-deoxyadenosine；N⁶-benzyl-2'-deoxyadenosine；6-N-(benzyl)-2'-deoxyadenosine；N6-benzyl 2'-deoxyadenosine；1-(6-benzylamino-purin-9-yl)-β-D-erythro-1,2-dideoxy-pentofuranose；N6-benzyl-2'-deoxyadenosine；N-Benzyl-2'-deoxyadenosine；(2R,3S,5R)-5-[6-(benzylamino)purin-9-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 37113-47-6
• 化学式: C₁₇H₁₉N₅O₃
• 分子量: 341.37
• InChiKey: NIMQVHDXSYNJJX-BFHYXJOUSA-N

物化性质

• 熔点：
  162-164 °C
• 沸点：
  651.9±65.0 °C(Predicted)
• 密度：
  1.53±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  5
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.35
• 拓扑面积：
  105
• 氢给体数：
  3
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-N⁶-(benzyl)-2'-deoxyadenosine 在 ammonium peroxydisulfate 、 phosphate buffer 作用下， 反应 2.0h， 以88%的产率得到2'-脱氧腺苷
  参考文献：
  名称：

  A Newly Devised Method for the Debenzylation ofN⁶-Benzyladenosines. A Convenient Synthesis of [6-¹⁵N]-Labeled Adenosines

  摘要：

  [6-N-15]-Labeled adenosine was conveniently prepared from inosine (1a) by the silylation-benzylamination of 1a and subsequent oxidative debenzylation with ammonium peroxydisulfate in a pH 7.2 buffer solution.

  DOI：

  10.1080/15257779408012148
• 作为产物：
  描述：

  2'-脱氧腺苷 在 sodium tetrahydroborate 、 溶剂黄146 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 5.0h， 生成 (-)-N⁶-(benzyl)-2'-deoxyadenosine
  参考文献：
  名称：

  A Novel Route to N6-Alkylated 2'-Deoxyadenosine Using Benzotriazole as a Synthetic Auxiliary.

  摘要：

  The N-6-alkylation of 2'-deoxyadenosine is achieved by sodium borohydride reduction of the adduct formed from benzotriazole, an aliphatic, aromatic or heteroaromatic aldehyde and 2'-deoxyadenosine. In some cases ethoxy adducts are isolated and reduced to give the target N-6-alkylated-2'-deoxyadenosine.

  DOI：

  10.3891/acta.chem.scand.53-0280

文献信息

• 3′-OH unblocked nucleotides and nucleosides base modified with non-cleavable, terminating groups and methods for their use in DNA sequencing
  申请人：LaserGen, Inc.

  公开号：US07893227B2

  公开（公告）日：2011-02-22

  Provided are novel nucleotides, nucleoside, and their derivatives described herein, that can be used in DNA sequencing technology and other types of DNA analysis. In one embodiment, the nucleotide or nucleoside with an unprotected 3′-OH group is derivatized at the nucleobase to include a fluorescent dye attached via a linker to a non-cleavable terminating group. The non-cleavable-fluorescent group is designed to terminate DNA synthesis so that DNA oligomers can be sequenced efficiently in a parallel format. These reagents and methods will lead to more accurate identification of polymorphisms and other valuable genetic information.

  提供的是本文描述的新型核苷酸、核苷和它们的衍生物，可用于DNA测序技术和其他类型的DNA分析。在一个实施例中，未保护的3'-OH基团的核苷酸或核苷在核碱基上被衍生，包括通过连接剂连接到不可切断终止基团的荧光染料。不可切断的荧光基团被设计为终止DNA合成，以便DNA寡聚体可以以并行格式高效测序。这些试剂和方法将导致对多态性和其他有价值的遗传信息更准确的识别。
• A Highly Facile and Efficient One-Step Synthesis of <i>N</i>⁶-Adenosine and <i>N</i>⁶-2‘-Deoxyadenosine Derivatives
  作者：Zhao-Kui Wan、Eva Binnun、Douglas P. Wilson、Jinbo Lee

  DOI：10.1021/ol052424+

  日期：2005.12.1

  [reaction: see text] A highly facile and efficient one-step synthesis of N6-adenosine and N6-2'-deoxyadenosine derivatives has been developed. Treatment of inosine or 2'-deoxyinosine, without protection of sugar hydroxyl groups, with alkyl or arylamines, in the presence of BOP and DIPEA in DMF, led to the formation of N6-adenosine and N6-2'-deoxyadenosine derivatives in good to excellent yields. Carcinogenic

  [反应：见正文]已开发出一种高度容易和高效的一步合成N6-腺苷和N6-2'-脱氧腺苷衍生物的方法。在DMF中存在BOP和DIPEA的情况下，在没有烷基糖基或芳基胺的情况下用烷基或芳基胺处理肌苷或2'-脱氧肌苷，导致形成N6-腺苷和N6-2'-脱氧腺苷衍生物，优异的产量。因此，由2'-脱氧肌苷直接以98％的产率直接合成了致癌的多环芳烃（PAH）N6-2'-脱氧腺苷加合物10和稀有DNA成分11。
• [EN] NUCLEOSIDE AND NUCLEOTIDE ANALOGUES AS CD73 INHIBITORS AND THERAPEUTIC USES THEREOF<br/>[FR] ANALOGUES DE NUCLÉOSIDES ET DE NUCLÉOTIDES EN TANT QU'INHIBITEURS DE CD73 ET UTILISATIONS THÉRAPEUTIQUES ASSOCIÉES
  申请人：ETERNITY BIOSCIENCE INC

  公开号：WO2018208727A1

  公开（公告）日：2018-11-15

  Nucleoside and nucleotide compounds and analogues, and pharmaceutically acceptable compositions thereof, as inhibitors of CD73 for the treatment of diseases or disorders associated with CD73 activities, especially cancers, and methods of preparing these compounds are disclosed.

  核苷和核苷酸化合物及其类似物，以及药学上可接受的组合物，作为CD73抑制剂用于治疗与CD73活性相关的疾病或障碍，尤其是癌症，以及制备这些化合物的方法被公开。
• Rapid and Selective Reduction of Amide Group by Borane-Amine Complexes in Acyl Protected Nucleosides
  作者：Zinaida A. Sergueeva、Dmitri S. Sergueev、Barbara Ramsay Shaw

  DOI：10.1080/15257770008033009

  日期：2000.1

  fast and selective reduction of a deoxynucleoside N-acyl group to a corresponding N-alkyl group. Three different nucleosides (dG, dA, and dC) each having one of three N-protecting groups (benzoyl, isobutyryl, or acetyl) were used to prepare N-alkylated nucleosides in good yields under mild conditions. Deoxyribose O-acyl protecting groups remain intact at the conditions of N-acyl group reduction.

  硼烷-胺络合物提供了脱氧核苷N-酰基异常快速且选择性的还原为相应的N-烷基。具有三个N-保护基团（苯甲酰基，异丁酰基或乙酰基）之一的三种不同的核苷（dG，dA和dC）用于在温和条件下以高收率制备N-烷基化的核苷。在N-酰基还原的条件下，脱氧核糖O-酰基保护基保持完整。
• Modification of the length and structure of the linker of N6-benzyladenosine modulates its selective antiviral activity against enterovirus 71
  作者：Mikhail S. Drenichev、Vladimir E. Oslovsky、Liang Sun、Aloys Tijsma、Nikolay N. Kurochkin、Vitali I. Tararov、Alexander O. Chizhov、Johan Neyts、Christophe Pannecouque、Pieter Leyssen、Sergey N. Mikhailov

  DOI：10.1016/j.ejmech.2016.01.036

  日期：2016.3

  high yields. Analysis of the structure-activity relationship clearly shows that the optimal size of the linker is limited to 2 or 3 atoms (compounds 4–7). 2′-Deoxyadenosine derivatives did not elicit any inhibitory or cytotoxic effect, while 5′-deoxynucleosides still induced some cell protective antiviral activity. Based on these observations, it can be hypothesized that there may be another mechanism

  最近，我们证明了N 6-异戊烯基腺苷，一种细胞分裂素核苷，对人肠病毒71的复制具有有效的选择性抗病毒作用。本研究致力于另一种天然化合物N 6-苄基腺苷的结构优化。我们主要研究腺嘌呤和苯环之间连接基的大小和性质，以及D-核糖残基的必要性。制备了30多种N 6-苄基腺苷类似物，并评估了它们的抗病毒特性。两种主要的制备方法：N 6-乙酰基-2'，3'，5'-tri- O-乙酰基腺苷可以在碱促进条件下通过烷基卤或在Mitsunobu反应中通过醇进行区域选择性烷基化。在室温下用4 M PrNH 2在MeOH中的溶液脱酰1天后，以高总收率获得所需产物。对结构-活性关系的分析清楚地表明，连接子的最佳尺寸限于2或3个原子（化合物4 – 7）。2'-脱氧腺苷衍生物没有引起任何抑制或细胞毒性作用，而5'-脱氧核苷仍然诱导了某些细胞保护性抗病毒活性。基于这些观察，可以假设除了可能的5'-三磷酸化继之以对RNA合