Di-(2-adenosinyl)disulfid | 50823-38-6

• 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: Di-(2-adenosinyl)disulfid
• 英文别名: 2-Thioadenosine disulfide；2,2''-disulfanediyl-bis-adenosine；(2R,3R,4S,5R)-2-[6-amino-2-[[6-amino-9-[(2R,3R,4S,5R)-3,4-dihydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-2-yl]disulfanyl]purin-9-yl]-5-(hydroxymethyl)oxolane-3,4-diol
• CAS: 50823-38-6
• 化学式: C₂₀H₂₄N₁₀O₈S₂
• 分子量: 596.605
• InChiKey: QUSKMXMVUYVMJY-MHARETSRSA-N

物化性质

• 沸点：
  1212.6±75.0 °C(Predicted)
• 密度：
  2.36±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -3
• 重原子数：
  40
• 可旋转键数：
  7
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  330
• 氢给体数：
  8
• 氢受体数：
  18

反应信息

• 作为反应物：
  描述：

  乙基硼酸 、 Di-(2-adenosinyl)disulfid 在 ammonium peroxydisulfate 、 9-mesityl-10-methylacridinium tetrafluoroborate 、 邻苯二酚 作用下， 以 水 为溶剂， 以68 %的产率得到2-Ethylthioadenosin
  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
• 作为产物：
  描述：

  2-硫代腺苷酸 在 ammonium peroxydisulfate 作用下， 以 水 为溶剂， 以91 %的产率得到Di-(2-adenosinyl)disulfid
  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