(2R,3S,5R)-5-[4-amino-5-(2-anthracen-9-ylethynyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-ol | 1429057-59-9

• 分子结构分类: 有机化合物 - 苯类化合物 - 蒽
• 英文名称: (2R,3S,5R)-5-[4-amino-5-(2-anthracen-9-ylethynyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-ol
• CAS: 1429057-59-9
• 化学式: C₂₇H₂₂N₄O₃
• 分子量: 450.497
• InChiKey: MBRIBEFFNLUGNK-RBZQAINGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  106
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (2R,3S,5R)-5-[4-amino-5-(2-anthracen-9-ylethynyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-ol 在 吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 0.5h， 生成
  参考文献：
  名称：

  Synthesis of solvatofluorochromic 7-arylethynylated 7-deaza-2′-deoxyadenosine derivatives: application to the design of environmentally sensitive fluorescent probes forming stable DNA duplexes

  摘要：

  We synthesized environmentally sensitive fluorescent (ESF) 7-deaza-2'-deoxyadenosine derivatives including ethynylanthracene substituted (atz)A (1) and ethynylnaphthalene substituted (nz)A (2a), (cnz)A (2b), (anz)A (2c), and (dnz)A (2d), and investigated their photophysical properties. Among them, only push-pull type cyano- and acetyl-substituted naphthylethynylated 7-deaza-2'-deoxyadenosine, (cnz)A (2b) and (anz)A (2c), exhibited remarkable solvatofluorochromic properties (Delta lambda = 71 and 63 nm, respectively). We incorporated non-solvatofluorochromic (atz)A (1) and solvatofluorochromic (cnz)A (2b) into oligodeoxynucleotides and found that (cnz)A (2b) forms a stable base pair with both thymine and cytosine, being accompanied by a change of fluorescence intensity. Such ESF nucleosides can be used for studying structures and functions of nucleic acids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.063
• 作为产物：
  描述：

  9-乙炔基蒽 、 5-碘-2'-脱氧结核菌素 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 2.0h， 生成 (2R,3S,5R)-5-[4-amino-5-(2-anthracen-9-ylethynyl)pyrrolo[2,3-d]pyrimidin-7-yl]-2-(hydroxymethyl)oxolan-3-ol
  参考文献：
  名称：

  Synthesis of solvatofluorochromic 7-arylethynylated 7-deaza-2′-deoxyadenosine derivatives: application to the design of environmentally sensitive fluorescent probes forming stable DNA duplexes

  摘要：

  We synthesized environmentally sensitive fluorescent (ESF) 7-deaza-2'-deoxyadenosine derivatives including ethynylanthracene substituted (atz)A (1) and ethynylnaphthalene substituted (nz)A (2a), (cnz)A (2b), (anz)A (2c), and (dnz)A (2d), and investigated their photophysical properties. Among them, only push-pull type cyano- and acetyl-substituted naphthylethynylated 7-deaza-2'-deoxyadenosine, (cnz)A (2b) and (anz)A (2c), exhibited remarkable solvatofluorochromic properties (Delta lambda = 71 and 63 nm, respectively). We incorporated non-solvatofluorochromic (atz)A (1) and solvatofluorochromic (cnz)A (2b) into oligodeoxynucleotides and found that (cnz)A (2b) forms a stable base pair with both thymine and cytosine, being accompanied by a change of fluorescence intensity. Such ESF nucleosides can be used for studying structures and functions of nucleic acids. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2013.02.063

文献信息

• Synthesis of solvatofluorochromic 7-arylethynylated 7-deaza-2′-deoxyadenosine derivatives: application to the design of environmentally sensitive fluorescent probes forming stable DNA duplexes
  作者：Azusa Suzuki、Kohki Kimura、Shinya Ishioroshi、Isao Saito、Nobukatsu Nemoto、Yoshio Saito

  DOI：10.1016/j.tetlet.2013.02.063

  日期：2013.5

  We synthesized environmentally sensitive fluorescent (ESF) 7-deaza-2'-deoxyadenosine derivatives including ethynylanthracene substituted (atz)A (1) and ethynylnaphthalene substituted (nz)A (2a), (cnz)A (2b), (anz)A (2c), and (dnz)A (2d), and investigated their photophysical properties. Among them, only push-pull type cyano- and acetyl-substituted naphthylethynylated 7-deaza-2'-deoxyadenosine, (cnz)A (2b) and (anz)A (2c), exhibited remarkable solvatofluorochromic properties (Delta lambda = 71 and 63 nm, respectively). We incorporated non-solvatofluorochromic (atz)A (1) and solvatofluorochromic (cnz)A (2b) into oligodeoxynucleotides and found that (cnz)A (2b) forms a stable base pair with both thymine and cytosine, being accompanied by a change of fluorescence intensity. Such ESF nucleosides can be used for studying structures and functions of nucleic acids. (C) 2013 Elsevier Ltd. All rights reserved.