| 1246033-83-9

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• CAS: 1246033-83-9
• 化学式: C₁₂H₁₄ClN₅O₂S
• 分子量: 327.794
• InChiKey: WZMOWQFZLVDDRY-VISXPRAWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.83
• 重原子数：
  21.0
• 可旋转键数：
  1.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  88.08
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二碘甲烷 、 氨 、 碘 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 5.75h， 生成
  参考文献：
  名称：

  Discovery of A New Human A_2A Adenosine Receptor Agonist, Truncated 2-Hexynyl-4′-thioadenosine

  摘要：

  The truncated C2- and C8-substituted 4'-thioadenosine derivatives 4a-d were synthesized from D-mannose, using palladium-Catalyzed cross-coupling reactions as key steps. In this study, an A(3) adenosine receptor. (AR) antagonist, truncated 4'-thioadenosine derivative 3, was successfully converted into a potent A(2A) AR agonist 4a (K-i = 7.19 +/- 0.6 nM) by appending a 2-hexynyl group at the C2-position of a derivative of 3 that was N-6-substituted. However, C8-substitution greatly reduced binding affinity at the human A(2A) AR. All synthesized compounds 4a-d maintained their affinity at the human A(3) AR, but 4a was found to be a competitive A(3) AR antagonist/A(2A) AR agonist in cyclic AMP assays. This study indicates that the truncated C2-substituted 4'-thioadenosine derivatives 4a and 4b can serve as novel templates for the development of new A(2A) AR ligands.

  DOI：

  10.1021/ml1001823
• 作为产物：
  描述：

  (3aR,6aS)-2,2-dimethyltetrahydrothieno[3,4-d][1,3]dioxol-4-yl acetate 、 alkaline earth salt of/the/ methylsulfuric acid 在 三氟甲磺酸三甲基硅酯 作用下， 以 1,2-二氯乙烷 为溶剂， 反应 3.0h， 以30%的产率得到
  参考文献：
  名称：

  Discovery of A New Human A_2A Adenosine Receptor Agonist, Truncated 2-Hexynyl-4′-thioadenosine

  摘要：

  The truncated C2- and C8-substituted 4'-thioadenosine derivatives 4a-d were synthesized from D-mannose, using palladium-Catalyzed cross-coupling reactions as key steps. In this study, an A(3) adenosine receptor. (AR) antagonist, truncated 4'-thioadenosine derivative 3, was successfully converted into a potent A(2A) AR agonist 4a (K-i = 7.19 +/- 0.6 nM) by appending a 2-hexynyl group at the C2-position of a derivative of 3 that was N-6-substituted. However, C8-substitution greatly reduced binding affinity at the human A(2A) AR. All synthesized compounds 4a-d maintained their affinity at the human A(3) AR, but 4a was found to be a competitive A(3) AR antagonist/A(2A) AR agonist in cyclic AMP assays. This study indicates that the truncated C2-substituted 4'-thioadenosine derivatives 4a and 4b can serve as novel templates for the development of new A(2A) AR ligands.

  DOI：

  10.1021/ml1001823