N⁶-(3-chlorobenzyl)adenosine | 23660-97-1

• 分子结构分类: 有机化合物 - 核苷、核苷酸和类似物 - 嘌呤核苷
• 英文名称: N⁶-(3-chlorobenzyl)adenosine
• 英文别名: N⁶-(3-chloro-benzyl)-adenosine；6-(3-chlorobenzylamino)purine riboside；(2R,3R,4S,5R)-2-[6-(3-Chloro-benzylamino)-purin-9-yl]-5-hydroxymethyl-tetrahydro-furan-3,4-diol；(2R,3R,4S,5R)-2-[6-[(3-chlorophenyl)methylamino]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 23660-97-1
• 化学式: C₁₇H₁₈ClN₅O₄
• 分子量: 391.814
• InChiKey: YRFQIOJJXMEZGA-LSCFUAHRSA-N

物化性质

• 熔点：
  164-165 °C
• 沸点：
  707.9±70.0 °C(Predicted)
• 密度：
  1.70±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  27
• 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：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  N⁶-(3-chlorobenzyl)adenosine 、 N,N'-二(三氟乙酰基)-L-高胱氨酸二甲酯 在 三丁基膦 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 以21 %的产率得到methyl S-(((2S,3S,4R,5R)-5-(6-((3-chlorobenzyl)amino)-9H-purin-9-yl)-3,4-dihydroxytetrahydrofuran-2-yl)methyl)-N-(2,2,2-trifluoroacetyl)-L-homocysteinate
  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：

  6-氯嘌呤核苷 、 3-氯苄胺 以 乙醇 为溶剂， 以96 %的产率得到N⁶-(3-chlorobenzyl)adenosine
  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

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。
• 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
• US8119614B2
  申请人：——

  公开号：US8119614B2

  公开（公告）日：2012-02-21