2-amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-((4-methoxynaphthalen-1-yl)ethynyl)-1,9-dihydro-6H-purin-6-one | 1380681-02-6

• 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-amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-((4-methoxynaphthalen-1-yl)ethynyl)-1,9-dihydro-6H-purin-6-one
• CAS: 1380681-02-6
• 化学式: C₂₃H₂₁N₅O₅
• 分子量: 447.45
• InChiKey: WTWYBYACDAYIHO-KVSKMBFKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33.0
• 可旋转键数：
  3.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  148.51
• 氢给体数：
  4.0
• 氢受体数：
  9.0

反应信息

• 作为反应物：
  描述：

  2-amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-((4-methoxynaphthalen-1-yl)ethynyl)-1,9-dihydro-6H-purin-6-one 在 吡啶 、 4-二甲氨基吡啶 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 20.0h， 生成 N'-(9-((2R,4S,5R)-5-((bis(4-methoxyphenyl)(phenyl)methoxy)methyl)-4-hydroxytetrahydrofuran-2-yl)-8-((4-methoxynaphthalen-1-yl)ethynyl)-6-oxo-6,9-dihydro-1H-purin-2-yl)-N,N-dimethylformimidamide
  参考文献：
  名称：

  Fluorometric detection of adenine in target DNA by exciplex formation with fluorescent 8-arylethynylated deoxyguanosine

  摘要：

  We demonstrated an intriguing method to discriminate adenine by incident appearance of an intense new emission via exciplex formation in hybridization of target DNA with newly designed fluorescent 8-arylethynylated deoxyguanosine derivatives. We described the synthesis of such highly electron donating fluorescent guanosine derivatives and their incorporation into DNA oligomers which may be used for the structural study and the fluorometric analysis of nucleic acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.011
• 作为产物：
  描述：

  1-碘-4-甲氧基萘 、 8-ethynyl-2'-deoxyguanosine 在 copper(l) iodide 、 四(三苯基膦)钯 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 3.0h， 以59%的产率得到2-amino-9-((2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)tetrahydrofuran-2-yl)-8-((4-methoxynaphthalen-1-yl)ethynyl)-1,9-dihydro-6H-purin-6-one
  参考文献：
  名称：

  Fluorometric detection of adenine in target DNA by exciplex formation with fluorescent 8-arylethynylated deoxyguanosine

  摘要：

  We demonstrated an intriguing method to discriminate adenine by incident appearance of an intense new emission via exciplex formation in hybridization of target DNA with newly designed fluorescent 8-arylethynylated deoxyguanosine derivatives. We described the synthesis of such highly electron donating fluorescent guanosine derivatives and their incorporation into DNA oligomers which may be used for the structural study and the fluorometric analysis of nucleic acids. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.04.011