N⁶-methoxy-2-[2-(trimethylsilyl)ethynyl]adenosine | 672299-23-9

• 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: N⁶-methoxy-2-[2-(trimethylsilyl)ethynyl]adenosine
• 英文别名: (4S,2R,3R,5R)-2-{2-(3,3-dimethyl-3-silabut-1-ynyl)-6-(methoxyamino)purin-9-yl}-5-(hydroxymethyl)oxolane-3,4-diol；N6-methoxy-2-[2-(trimethylsilyl)ethynyl]adenosine；(2R,3S,4R,5R)-2-(hydroxymethyl)-5-[6-(methoxyamino)-2-(2-trimethylsilylethynyl)purin-9-yl]oxolane-3,4-diol
• CAS: 672299-23-9
• 化学式: C₁₆H₂₃N₅O₅Si
• 分子量: 393.475
• InChiKey: UOJJCTHGWLSJEL-RVXWVPLUSA-N

物化性质

• 熔点：
  100-102 °C (decomp)(Solv: acetonitrile (75-05-8))
• 沸点：
  642.8±65.0 °C(Predicted)
• 密度：
  1.43±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  -0.36
• 重原子数：
  27
• 可旋转键数：
  6
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  135
• 氢给体数：
  4
• 氢受体数：
  9

反应信息

• 作为反应物：
  描述：

  N⁶-methoxy-2-[2-(trimethylsilyl)ethynyl]adenosine 在 氢氧化钾 作用下， 以 甲醇 为溶剂， 反应 1.0h， 以69%的产率得到2-ethynyl-N⁶-methoxyadenosine
  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
• 作为产物：
  描述：

  2',3',5'-三-O-乙酰-6-氯-2-碘嘌呤核苷 在 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 氨 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 N,N-二甲基甲酰胺 为溶剂， 反应 168.0h， 生成 N⁶-methoxy-2-[2-(trimethylsilyl)ethynyl]adenosine
  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

文献信息

• <i>N</i>⁶-Methoxy-2-alkynyladenosine Derivatives as Highly Potent and Selective Ligands at the Human A₃ Adenosine Receptor
  作者：Rosaria Volpini、Diego Dal Ben、Catia Lambertucci、Sara Taffi、Sauro Vittori、Karl-Norbert Klotz、Gloria Cristalli

  DOI：10.1021/jm060963u

  日期：2007.3.1

  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.