(2R,3R,4S,5R)-2-(6-amino-2-((cyclopentylmethyl)thio)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol | 57953-60-3

• 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: (2R,3R,4S,5R)-2-(6-amino-2-((cyclopentylmethyl)thio)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol
• 英文别名: 2-(cyclopentylmethylthio)adenosine
• CAS: 57953-60-3
• 化学式: C₁₆H₂₃N₅O₄S
• 分子量: 381.456
• InChiKey: LNUBTLQSVBMBPS-SDBHATRESA-N

反应信息

• 作为产物：
  描述：

  2-硫代腺苷酸 、 (环戊基甲基)硼酸 在 ammonium peroxydisulfate 、 9-mesityl-10-methylacridinium tetrafluoroborate 、 邻苯二酚 作用下， 以 水 为溶剂， 生成 (2R,3R,4S,5R)-2-(6-amino-2-((cyclopentylmethyl)thio)-9H-purin-9-yl)-5-(hydroxymethyl)tetrahydrofuran-3,4-diol 、
  参考文献：
  名称：

  Visible Light‐Mediated Late‐Stage Thioetherification of Mercaptopurine Derivatives

  摘要：

  We present herein a novel photo‐mediated homolytic C‐S bond formation for the preparation of alkylthiopurines and alkylthiopurine nucleosides. Despite the presence of reactive sites for the Minisci reaction, chemoselective S‐alkylation remained the predominant pathway. This method allows for the late‐stage introduction of a broad spectrum of alkyl groups onto the sulfur atom of unprotective mercaptopurine derivatives, encompassing 2‐, 6‐, and 8‐mercaptopurine rings. Organoborons serve as efficient and eco‐friendly alkylating reagents, providing advantages in terms of readily availability, stability, and reduced toxicity. Further derivatization of the thioetherified nucleosides, together with anti‐tumor assays, led to the discovery of potent anti‐tumor agents with an IC50 value reaching 6.1 µM (Comp. 31 for Jurkat).

  DOI：

  10.1002/chem.202401774