N⁶-(1-pyrenylmethyl)adenosine

• 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-(1-pyrenylmethyl)adenosine
• 英文别名: N6-(1-Pyrenylmethyl)adenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(pyren-1-ylmethylamino)purin-9-yl]oxolane-3,4-diol
• 化学式: C₂₇H₂₃N₅O₄
• 分子量: 481.511
• InChiKey: RLTHPBOMZZRVCC-GVDONAMHSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.22
• 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256 mg的产率得到N⁶-(1-pyrenylmethyl)adenosine
  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

• Dual-Action Compounds Targeting Adenosine A2A Receptor and Adenosine Transporter for Prevention and Treatment of Neurodegenerative Diseases
  申请人：Lin Yun-Lian

  公开号：US20120295863A1

  公开（公告）日：2012-11-22

  The present invention provides therapeutic agents for preventing and treating neurodegenerative diseases. These agents synergistically target both the adenosine A 2A receptor (A 2A R) and the equilibrative nucleoside transporter 1 (ENT1).

  本发明提供了治疗神经退行性疾病的治疗剂。这些治疗剂协同作用于腺苷A2A受体（A2AR）和平衡核苷转运蛋白1（ENT1）。
• New tools in nucleoside toolbox of tick-borne encephalitis virus reproduction inhibitors
  作者：Alexey A. Orlov、Mikhail S. Drenichev、Vladimir E. Oslovsky、Nikolay N. Kurochkin、Pavel N. Solyev、Liubov I. Kozlovskaya、Vladimir A. Palyulin、Galina G. Karganova、Sergey N. Mikhailov、Dmitry I. Osolodkin

  DOI：10.1016/j.bmcl.2017.01.040

  日期：2017.3

  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.