9-(2-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine | 879398-56-8

• 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: 9-(2-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine
• CAS: 879398-56-8
• 化学式: C₂₂H₂₁N₉O₄
• 分子量: 475.467
• InChiKey: SDZJJFSTSGGQOC-OQYZPLRDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.52
• 重原子数：
  35.0
• 可旋转键数：
  5.0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  169.02
• 氢给体数：
  2.0
• 氢受体数：
  10.0

反应信息

• 作为反应物：
  描述：

  9-(2-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine 在 氨 、 三苯基膦 作用下， 以 四氢呋喃 、 甲醇 、 水 为溶剂， 反应 50.0h， 生成 9-(3-amino-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine
  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：

  N6-methyl-2-phenylethynyl-9-(tetrahydropyran-2-yl)adenine 在 N,O-双三甲硅基乙酰胺 、 三氟甲磺酸三甲基硅酯 、 三氟乙酸 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 反应 11.0h， 生成 9-(2-acetyl-3-azido-3-deoxy-5-methylcarbamoyl-β-D-ribofuranosyl)-N⁶-methyl-2-phenylethynyladenine
  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