N6-(9-蒽基甲基)腺苷 | 94617-16-0

• 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-(9-蒽基甲基)腺苷
• 英文名称: N⁶-(9-anthracenylmethyl)adenosine
• 英文别名: N⁶-(9-anthranylmethyl)adenosine；N⁶-(9-anthrylmethyl)adenosine；N6-(9-anthranylmethyl)adenosine；(2R,3R,4S,5R)-2-(6-((Anthracen-9-ylmethyl)amino)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol；(2R,3R,4S,5R)-2-[6-(anthracen-9-ylmethylamino)purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 94617-16-0
• 化学式: C₂₅H₂₃N₅O₄
• 分子量: 457.489
• InChiKey: PIRKENBEBYLCJH-PTGPVQHPSA-N

物化性质

• 沸点：
  821.1±75.0 °C(Predicted)
• 密度：
  1.56±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.6
• 重原子数：
  34
• 可旋转键数：
  5
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  126
• 氢给体数：
  4
• 氢受体数：
  8

反应信息

• 作为产物：
  描述：

  在 正丙胺 作用下， 以 甲醇 为溶剂， 反应 24.0h， 以80 mg的产率得到N6-(9-蒽基甲基)腺苷
  参考文献：
  名称：

  New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors

  摘要：

  Design and development of nucleoside analogs is an established strategy in the antiviral drug discovery field. Nevertheless, for many viruses the coverage of structure-activity relationships (SAR) in the nucleoside chemical space is not sufficient. Here we present the nucleoside SAR exploration for tick-borne encephalitis virus (TBEV), a member of Flavivirus genus. Promising antiviral activity may be achieved by introduction of large hydrophobic substituents in the position 6 of adenosine or bulky silyl groups to the position 5'. Introduction of methyls to the ribose moiety does not lead to inhibition of TBEV reproduction. Possible mechanisms of action of these nucleosides include the inhibition of viral entry or interaction with TBEV non-structural protein 5 methyltransferase or RNA-dependent RNA polymerase domains. (C) 2017 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2017.01.040

文献信息

• N6-(Arylalkyl)adenosines. Identification of N6-(9-fluorenylmethyl)adenosine as a highly potent agonist for the adenosine A2 receptor
  作者：B. K. Trivedi、J. A. Bristol、R. F. Bruns、S. J. Haleen、R. P. Steffen

  DOI：10.1021/jm00396a044

  日期：1988.1

  Several N6-(arylalkyl)adenosines related to N6-benzyladenosine were synthesized, and their A1 and A2 adenosine receptor binding affinities were determined. The annulated derivative N6-(1-naphthylmethyl)adenosine resulted in a very potent A2 agonist (A1 Ki = 24 nM, A2 Ki = 9.1 nM), whereas N6-(9-anthracenylmethyl)adenosine was virtually inactive (A1 Ki = 9,000 nM, A2 Ki = 29,000 nM). Interestingly,

  合成了几种与N6-苄基腺苷有关的N6-（芳烷基）腺苷，并确定了它们的A1和A2腺苷受体结合亲和力。环状衍生物N6-（1-萘甲基）腺苷产生非常有效的A2激动剂（A1 Ki = 24 nM，A2 Ki = 9.1 nM），而N6-（9-蒽基甲基）腺苷实际上是无活性的（A1 Ki = 9,000 nM ，A 2 Ki = 29,000 nM）。有趣的是，结构相似的N6-（9-芴基甲基）腺苷是迄今为止报道的最有效的A2激动剂，A2结合的Ki为4.9 nM，A1结合的Ki为5.1 nM。N6-9-芴基腺苷和N6- [2-（9-芴基）乙基]腺苷的同系物对任一腺苷受体显示很少或没有活性。这些试剂对离体大鼠心脏的心率和冠状动脉血流的影响分别与其A1和A2结合亲和力平行。