2-iodo-N⁶-methyl-9-(tetrahydropyran-2-yl)adenine | 879398-53-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 咪唑并嘧啶类
• 英文名称: 2-iodo-N⁶-methyl-9-(tetrahydropyran-2-yl)adenine
• 英文别名: 2-iodo-N-methyl-9-(oxan-2-yl)purin-6-amine
• CAS: 879398-53-5
• 化学式: C₁₁H₁₄IN₅O
• 分子量: 359.17
• InChiKey: LMZYKFYEEHJCAA-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  18
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.55
• 拓扑面积：
  64.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-iodo-N⁶-methyl-9-(tetrahydropyran-2-yl)adenine 在 bis-triphenylphosphine-palladium(II) chloride copper(l) iodide 、 三乙胺 、 三氟乙酸 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 4.0h， 生成 N⁶-methyl-2-(phenylethynyl)adenine
  参考文献：
  名称：

  Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands

  摘要：

  We investigated the A(3)AR affinity and selectivity of a series of 2-substituted 3'-azido and 3'-amino adenosine derivatives as well as some 5-uronamide derivatives thereof. All compounds showed high A3AR selectivity. While the 3'-azides appeared to be A3AR antagonists with moderate A3AR affinity, their 3'-amino congeners exhibit significantly improved A3AR affinity and behave as partial agonists. For both the 3'-azides and the 3'-amines, the 5'-methylcarbamoyl modification improved the overall affinity. Introduction of a 2-phenylethynyl substituent provided high affinity for the A3AR. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.062
• 作为产物：
  描述：

  盐酸甲胺 、 6-chloro-2-iodo-9-(tetrahydropyran-2-yl)purine 在 4-二甲氨基吡啶 作用下， 以 乙醇 为溶剂， 以81%的产率得到2-iodo-N⁶-methyl-9-(tetrahydropyran-2-yl)adenine
  参考文献：
  名称：

  Synthesis of hypermodified adenosine derivatives as selective adenosine A3 receptor ligands

  摘要：

  We investigated the A(3)AR affinity and selectivity of a series of 2-substituted 3'-azido and 3'-amino adenosine derivatives as well as some 5-uronamide derivatives thereof. All compounds showed high A3AR selectivity. While the 3'-azides appeared to be A3AR antagonists with moderate A3AR affinity, their 3'-amino congeners exhibit significantly improved A3AR affinity and behave as partial agonists. For both the 3'-azides and the 3'-amines, the 5'-methylcarbamoyl modification improved the overall affinity. Introduction of a 2-phenylethynyl substituent provided high affinity for the A3AR. (c) 2005 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2005.09.062