N-[(3-甲氧基苯基)甲基]-腺苷 | 101565-95-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 中文名称: N-[(3-甲氧基苯基)甲基]-腺苷
• 英文名称: N⁶-(3-methoxybenzyl)adenosine
• 英文别名: 6-N-(3-methoxybenzyl)adenosine；6-(3-methoxybenzylamino)purine riboside；Adenosine, N-[(3-methoxyphenyl)methyl]-；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-[(3-methoxyphenyl)methylamino]purin-9-yl]oxolane-3,4-diol
• CAS: 101565-95-1
• 化学式: C₁₈H₂₁N₅O₅
• 分子量: 387.395
• InChiKey: YUPMHVHUPBAVAS-SCFUHWHPSA-N

物化性质

• 熔点：
  162-163℃
• 溶解度：
  DMSO（微溶）、甲醇（微溶、超声处理）

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

• 作为产物：
  描述：

  3-甲氧基苄胺 、 6-氯嘌呤核苷 在 三乙胺 作用下， 以 正丁醇 为溶剂， 反应 4.0h， 生成 N-[(3-甲氧基苯基)甲基]-腺苷
  参考文献：
  名称：

  Preparation, biological activity and endogenous occurrence of N6-benzyladenosines

  摘要：

  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.

  DOI：

  10.1016/j.bmc.2007.03.038

文献信息

• 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。
• Synthesis of Substituted-Benzyl and Sugar-Modified Analogues of 6-<i>N</i>-(4-Nitrobenzyl)adenosine and Their Interactions with “<i>ES</i>” Nucleoside Transport Systems
  作者：Morris J. Robins、Jun-ichi Asakura、Masakatsu Kaneko、Susumu Shibuya、Ewa S. Jakobs、Francisca R. Agbanyo、Carol E. Cass、Alan R. P. Paterson

  DOI：10.1080/15257779408012177

  日期：1994.7

  Four classes of 6-X-benzylated purine nucleosides, (i) 6-N-(substituted-benzyl)adenosines, (ii) 6-N-(4-nitrobenzyl)adenine nucleosides with modified sugars, (iii) 6-N(S)-(4-azidobenzy1) derivatives of adenosine, 6-thioinosine, and 6-thioguanosine, and (iv) 6-N-4-N-[acyl(sulfonyl)amino]benzyl} adenosines, were synthesized and their binding interactions with ''es-NT'' (equilibrative, inhibitor-sensitive nucleoside transport) systems were studied. Several tight-binding analogues were found.
• 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
• [EN] SUBSTITUTION DERIVATIVES OF N<6>-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<br/>[FR] DERIVES DE SUBSTITUTION DE N<6>-BENZYLE ADENOSINE, METHODES DE PREPARATION ASSOCIEES, LEUR UTILISATION POUR REALISER DES MEDICAMENTS, DES PREPARATIONS COSMETIQUES ET DES REGULATEURS DE CROISSANCE ; PREPARATIONS PHARMACEUTIQUES, COSMETIQUES ET REGULATEURS DE CROISSANCE CONTENANT CES COMPOSES
  申请人：USTAV EX BOTAN AKADEMIE VED CE

  公开号：WO2004058791A2

  公开（公告）日：2004-07-15

  The invention concerns novel substitution derivatives of N6-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 N6-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.