2-[(4-acetylphenyl)ethynyl]-N⁶-methoxy-5'-N-methylcarboxamidoadenosine

• 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: 2-[(4-acetylphenyl)ethynyl]-N⁶-methoxy-5'-N-methylcarboxamidoadenosine
• 英文别名: {(2S,3S,4R,5R)-5-{2-[2-(4-acetylphenyl)ethynyl]-6-(methoxyamino)purin-9-yl}-3,4-dihydroxyoxolan-2-yl}-N-methylcarboxamide；2-[(4-acetylphenyl)ethynyl]-N6-methoxy-5''-N-methylcarboxamidoadenosine；(2S,3S,4R,5R)-5-[2-[2-(4-acetylphenyl)ethynyl]-6-(methoxyamino)purin-9-yl]-3,4-dihydroxy-N-methyloxolane-2-carboxamide
• 化学式: C₂₂H₂₂N₆O₆
• 分子量: 466.453
• InChiKey: VGHWQWQBYNQEDX-RQXXJAGISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.5
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.32
• 拓扑面积：
  161
• 氢给体数：
  4
• 氢受体数：
  10

反应信息

• 作为产物：
  描述：

  6-amino-2-iodo-2',3'-O-isopropylidene-5'-N-methylcarboxamidoadenosine 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 甲酸 、 二碘甲烷 、 三乙胺 、 亚硝酸异戊酯 作用下， 以 四氢呋喃 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 27.5h， 生成 2-[(4-acetylphenyl)ethynyl]-N⁶-methoxy-5'-N-methylcarboxamidoadenosine
  参考文献：
  名称：

  N⁶-Methoxy-2-alkynyladenosine Derivatives as Highly Potent and Selective Ligands at the Human A₃ Adenosine Receptor

  摘要：

  A new series of N-6-methoxy-2-(ar)alkynyladenosine derivatives has been synthesized and tested at the human recombinant adenosine receptors. Binding studies demonstrated that the new compounds possess high affinity and selectivity for the A(3) subtype. Among them, compounds bearing an N-methylcarboxamido substituent in the 4'-position showed the highest A(3) affinity and selectivity. In particular, the N-6-methoxy-2-p-acetylphenylethynylMECA (40; K-i A(3) = 2.5 nM, A(3) selectivity versus A(1) = 21 500 and A(2A) = 4200) results in one of the most potent and selective agonists at the human A(3) adenosine receptor reported so far. Furthermore, functional assay, performed with selected new compounds, revealed that the presence of an alkylcarboxamido group in the 4'-position seems to be essential to obtain full agonists at the A(3) subtype. Finally, results of molecular docking analysis were in agreement with binding and functional data and could explain the high affinity and potency of the new compounds.

  DOI：

  10.1021/jm060963u