N6-(2-甲氧苄基)腺苷 | 23660-98-2

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N6-(2-甲氧苄基)腺苷
• 英文名称: N⁶-(o-methoxybenzyl)adenosine
• 英文别名: N⁶-(2-methoxybenzyl)adenosine；N6-(2-methoxybenzyl)adenosine；N6-(o-methoxybenzyl)adenosine；N⁶-(2-methoxy-benzyl)-adenosine；6-(2-methoxybenzylamino)purine riboside；N6-(o-methoxybenzyl)-adenosine；Adenosine, N-[(2-methoxyphenyl)methyl]-；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(2-methoxyphenyl)methylamino]purin-9-yl]oxolane-3,4-diol
• CAS: 23660-98-2
• 化学式: C₁₈H₂₁N₅O₅
• 分子量: 387.395
• InChiKey: RDBVQLRPLJFYBG-SCFUHWHPSA-N

物化性质

• 熔点：
  164-166 °C
• 沸点：
  699.8±65.0 °C(Predicted)
• 密度：
  1.60±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  28
• 可旋转键数：
  6
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.39
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  甲醇 、 potassium tetrachloroplatinate 、 N6-(2-甲氧苄基)腺苷 以 水 为溶剂， 以70%的产率得到
  参考文献：
  名称：

  N6-Benzyladenosine Derivatives as Novel N-Donor Ligands of Platinum(II) Dichlorido Complexes

  摘要：

  合成了铂(II)复合物trans-[PtCl2(Ln)2]∙xSolv 1–13（Solv = H2O或CH3OH），这些复合物涉及以N6-苄基腺苷为基础的N供体配体；Ln代表N6-(2-甲氧基苄基)腺苷（L1，复合物1中涉及），N6-(4-甲氧基苄基)腺苷（L2，复合物2），N6-(2-氯苄基)腺苷（L3，复合物3），N6-(4-氯苄基)腺苷（L4，复合物4），N6-(2-羟基苄基)腺苷（L5，复合物5），N6-(3-羟基苄基)腺苷（L6，复合物6），N6-(2-羟基-3-甲氧基苄基)腺苷（L7，复合物7），N6-(4-氟苄基)腺苷（L8，复合物8），N6-(4-甲基苄基)腺苷（L9，复合物9），2-氯-N6-(3-羟基苄基)腺苷（L10，复合物10），2-氯-N6-(4-羟基苄基)腺苷（L11，复合物11），2-氯-N6-(2-羟基-3-甲氧基苄基)腺苷（L12，复合物12）和2-氯-N6-(2-羟基-5-甲基苄基)腺苷（L13，复合物13）。通过元素分析、质谱、红外光谱以及多核（1H、13C、195Pt和15N）和二维核磁共振谱对这些化合物进行了表征，证明了适当的N6-苄基腺苷衍生物的N7配位模式和标题复合物的反式几何结构。复合物1–13在体外对选定的人癌细胞系（HOS和MCF7；IC50 > 50.0 µM）被发现无毒。然而，通过ESI-MS研究发现，它们能够通过相对简单的1:1置换机制（一个Ln分子被一个L-甲硫氨酸分子替换）与生理水平的含硫生物源生物分子L-甲硫氨酸相互作用，从而形成混合氮/硫配体的二氯铂(II)配位物。

  DOI：

  10.3390/molecules18066990
• 作为产物：
  描述：

  邻甲氧基苄胺 、 6-氯嘌呤核苷 在 三乙胺 作用下， 以 丙醇 为溶剂， 反应 11.0h， 以76%的产率得到N6-(2-甲氧苄基)腺苷
  参考文献：
  名称：

  N6-苄基腺苷类似物作为潜在抗弓形虫药物的合成，生物学评估和分子建模研究。

  摘要：

  弓形虫是导致弓形虫病的机会病原体。刚地弓形虫是一种嘌呤营养缺陷型，不能从头进行嘌呤生物合成，并且依赖于挽救途径来满足其嘌呤需求。腺苷激酶（EC.2.7.1.20）是挽救这些寄生虫中嘌呤的主要酶。建立了6-苄基硫代肌苷和类似物作为弓形虫的“颠覆性底物”，而不是人腺苷激酶的“颠覆性底物”。因此，这些化合物作为选择性的抗弓形虫剂。在本研究中，一系列N（6）-苄基腺苷类似物是由6-氯嘌呤核糖苷与取代的苄胺通过溶液相平行合成合成的。评价这些N（6）-苄基腺苷类似物与纯化的弓形虫腺苷激酶的结合亲和力。此外，在细胞培养中测试了这些化合物的抗弓形虫功效和宿主毒性。与未取代的N（6）-苄基腺苷相比，芳香环上的某些取代基改善了对弓形虫腺苷激酶的结合亲和力。类似地，改变芳环上取代基的类型和位置导致作为抗弓形虫剂的效力和选择性程度不同。在合成的类似物中，N（6）-（2,4-二甲氧基苄基）腺苷显示出最有利的抗弓形虫

  DOI：

  10.1016/j.bcp.2007.01.026

文献信息

• Platinum(II) Oxalato Complexes Involving Adenosine-Based N-Donor Ligands: Synthesis, Characterization and Cytotoxicity Evaluation
  作者：Pavel Štarha、Igor Popa、Zdeněk Trávníček

  DOI：10.3390/molecules19033832

  日期：——

  A one-step synthetic procedure using the reaction of potassium bis(oxalato)platinate(II) with the corresponding N6-benzyladenosine derivative (nL) provided the [Pt(ox)(nL)2]∙1.5H2O oxalato (ox) complexes 1–5, involving the nL molecules as monodentate coordinated N-donor ligands. The complexes were thoroughly characterized by elemental analysis, multinuclear (1H, 13C, 15N, 195Pt) and two dimensional

  使用双(草酸)铂酸钾 (II) 与相应的 N6-苄基腺苷衍生物 (nL) 反应的一步合成程序提供了 [Pt(ox)(nL)2]∙1.5H2O 草酸 (ox) 配合物 1 –5，涉及作为单齿配位 N-供体配体的 nL 分子。通过元素分析、多核（1H、13C、15N、195Pt）和二维核磁共振、红外和拉曼光谱以及质谱对配合物进行了彻底表征，证明了它们的组成和纯度以及 nL 通过 N7 原子的配位。嘌呤部分。[Pt(ox)(4FL)2] (5) 的几何结构在 B3LYP/LANLTZ/6-311G** 理论水平进行了优化。筛选了复合物对两种人类癌细胞系（HOS 骨肉瘤和 MCF7 乳腺癌）的体外细胞毒性，
• 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。
• Adenosine Analogues as Inhibitors of <i>Trypanosoma </i><i>b</i><i>rucei </i>Phosphoglycerate Kinase:  Elucidation of a Novel Binding Mode for a 2-Amino-N⁶-Substituted Adenosine
  作者：Jerome C. Bressi、Jungwoo Choe、Melinda T. Hough、Frederick S. Buckner、Wesley C. Van Voorhis、Christophe L. M. J. Verlinde、Wim G. J. Hol、Michael H. Gelb

  DOI：10.1021/jm000287a

  日期：2000.11.1

  As part of a project aimed at structure-based design of adenosine analogues as drugs against African trypanosomiasis, N-6-, 2-amino-N-6-, and N-2-substituted adenosine analogues were synthesized and tested to establish structure-activity relationships for inhibiting Trypanosoma brucei glycosomal phosphoglycerate kinase (PGK), glyceraldehyde-3-phosphate dehydrogenase (GAPDH), and glycerol-3-phosphate dehydrogenase (GPDH). Evaluation of X-ray structures of parasite PGK, GAPDH, and GPDH complexed with their adenosyl-bearing substrates led us to generate a series of adenosine analogues which would target all three enzymes simultaneously. There was a modest preference by PGK for NG-substituted analogues bearing the 2-amino group. The best compound in this series, 2-amino-N-6-[2 "-(p-hydroxyphenyl)ethyl]adenosine (46b), displayed a 23-fold improvement over adenosine with an IC50 of 130 muM. 2-[[2 "-(p-Hydroxyphenyl)ethyl]amino]adenosine (46c) was a weak inhibitor of T. brucei PGK with an IC50 of 500 muM. To explore the potential of an additive effect that having the N-6 and N-2 substitutions in one molecule might provide, the best ligands from the two series were incorporated into N-6,N-2-disubstituted adenosine analogues to yield N-6-(2 " -phenylethyl)-2-[(2 " -phenylethyl)amino]adenosine (69) as a 30 muM inhibitor of T. brucei PGK which is 100-fold more potent than the adenosine template. In contrast, these series gave no compounds that inhibited parasitic GAPDH or GPDH more than 10-20% when tested at 1.0 mM. A 3.0 Angstrom X-ray structure of a T, brucei PGK/46b complex revealed a binding mode in which the nucleoside analogue was flipped and the ribosyl moiety adopted a syn conformation as compared with the previously determined binding mode of ADP. Molecular docking experiments using QXP and SAS program suites reproduced this "flipped and rotated" binding mode.
• 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