N⁶-(N'-(1-naphthyl)carbamoyl)-2'-deoxyadenosine | 658712-93-7

• 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-(N'-(1-naphthyl)carbamoyl)-2'-deoxyadenosine
• 英文别名: 2'-Deoxy-N-[(naphthalen-1-yl)carbamoyl]adenosine；1-[9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-6-yl]-3-naphthalen-1-ylurea
• CAS: 658712-93-7
• 化学式: C₂₁H₂₀N₆O₄
• 分子量: 420.428
• InChiKey: OPLWYTVHMQYUKK-GVDBMIGSSA-N

物化性质

• 密度：
  1.61±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.2
• 重原子数：
  31
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.24
• 拓扑面积：
  134
• 氢给体数：
  4
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  N⁶-(N'-(1-naphthyl)carbamoyl)-2'-deoxyadenosine 在 吡啶 、 四氮唑 、 4-二甲氨基吡啶 作用下， 以 二氯甲烷 为溶剂， 反应 23.0h， 生成
  参考文献：
  名称：

  Large Stabilization of a DNA Duplex by the Deoxyadenosine Derivatives Tethering an Aromatic Hydrocarbon Group

  摘要：

  Novel deoxyadenosine derivatives tethering a phenyl or naphthyl group by means of an amido linker have been synthesized, and these derivatives, stacking on the 5' end of a DNA duplex, provide free energy contributions equal to or greater than that of the Watson-Crick A/T base pair.

  DOI：

  10.1021/ja034465b
• 作为产物：
  描述：

  2'-脱氧腺苷 在 四丁基氟化铵 、 三乙胺 作用下， 以 四氢呋喃 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 9.08h， 生成 N⁶-(N'-(1-naphthyl)carbamoyl)-2'-deoxyadenosine
  参考文献：
  名称：

  Large Stabilization of a DNA Duplex by the Deoxyadenosine Derivatives Tethering an Aromatic Hydrocarbon Group

  摘要：

  Novel deoxyadenosine derivatives tethering a phenyl or naphthyl group by means of an amido linker have been synthesized, and these derivatives, stacking on the 5' end of a DNA duplex, provide free energy contributions equal to or greater than that of the Watson-Crick A/T base pair.

  DOI：

  10.1021/ja034465b

文献信息

• Molecular recognition of cationic phenothiazinium and phenoxazinium dyes with π-extended 2′-deoxyadenosine nucleotides
  作者：Karina Mondragón-Vásquez、Hugo Morales-Rojas

  DOI：10.1039/b913315a

  日期：——

  N 6-(N′-Arylcarbamoyl)-2′-deoxyadenosine-H-phosphonates displayed molecular recognition towards cationic phenothiazinium and phenoxazinium dyes in aqueous solutions; studies have shown that binding is driven mainly by aromatic interactions and that size and shape-complementarity of the aromatic rings in host and guest provides selectivity.

  N，6-(N'-芳基氨基甲酰基)-2'-脱氧腺苷-H-膦酸酯在水溶液中对阳离子型吩噻嗪和吩噻嗪染料分子表现出分子识别特性。研究表明，结合作用主要由芳香性相互作用驱动，受体和客体中芳香环的大小和形状互补性提供了选择性。
• Large Stabilization of a DNA Duplex by the Deoxyadenosine Derivatives Tethering an Aromatic Hydrocarbon Group
  作者：Shu-ichi Nakano、Yuuki Uotani、Shoji Nakashima、Yosuke Anno、Masayuki Fujii、Naoki Sugimoto

  DOI：10.1021/ja034465b

  日期：2003.7.1

  Novel deoxyadenosine derivatives tethering a phenyl or naphthyl group by means of an amido linker have been synthesized, and these derivatives, stacking on the 5' end of a DNA duplex, provide free energy contributions equal to or greater than that of the Watson-Crick A/T base pair.