4-[2-[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]ethynyl]naphthalene-1-carbonitrile | 1419164-80-9

• 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: 4-[2-[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]ethynyl]naphthalene-1-carbonitrile
• CAS: 1419164-80-9
• 化学式: C₂₃H₁₈N₆O₃
• 分子量: 426.434
• InChiKey: HBYJALZNJGKSFW-NLWGTHIKSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.1
• 重原子数：
  32
• 可旋转键数：
  4
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.22
• 拓扑面积：
  143
• 氢给体数：
  3
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  4-[2-[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]ethynyl]naphthalene-1-carbonitrile 在 吡啶 、 4-二甲氨基吡啶 、 三乙胺 作用下， 以 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 4.0h， 生成
  参考文献：
  名称：

  Naphthalene-based environmentally sensitive fluorescent 8-substituted 2′-deoxyadenosines: Application to DNA detection

  摘要：

  We synthesized various C8-naphthylethynylated 2'-deoxyadenosine derivatives and investigated their photophysical properties. Among them, cyano- and N,N-dimethylamino-substituted 8-naphthylethynylated 2'-deoxyadenosine derivatives ((cn)A and (dn)A) showed strong fluorescence with high quantum yields and a remarkable solvatofuorochromicity. In particular, fluorescence of N,N-dimethylamino-substituted (2,6dn)A was not quenched by neighboring guanines (Gs) when incorporated in DNA duplexes, in contrast to (cn)A. We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.029
• 作为产物：
  描述：

  4-溴-1-萘甲腈 、 8-ethynyl-2′-deoxyadenosine 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， 以46%的产率得到4-[2-[6-amino-9-[(2R,4S,5R)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]purin-8-yl]ethynyl]naphthalene-1-carbonitrile
  参考文献：
  名称：

  Naphthalene-based environmentally sensitive fluorescent 8-substituted 2′-deoxyadenosines: Application to DNA detection

  摘要：

  We synthesized various C8-naphthylethynylated 2'-deoxyadenosine derivatives and investigated their photophysical properties. Among them, cyano- and N,N-dimethylamino-substituted 8-naphthylethynylated 2'-deoxyadenosine derivatives ((cn)A and (dn)A) showed strong fluorescence with high quantum yields and a remarkable solvatofuorochromicity. In particular, fluorescence of N,N-dimethylamino-substituted (2,6dn)A was not quenched by neighboring guanines (Gs) when incorporated in DNA duplexes, in contrast to (cn)A. We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences. (c) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.029

文献信息

• Naphthalene-based environmentally sensitive fluorescent 8-substituted 2′-deoxyadenosines: Application to DNA detection
  作者：Azusa Suzuki、Naoya Takahashi、Yuji Okada、Isao Saito、Nobukatsu Nemoto、Yoshio Saito

  DOI：10.1016/j.bmcl.2012.11.029

  日期：2013.2

  We synthesized various C8-naphthylethynylated 2'-deoxyadenosine derivatives and investigated their photophysical properties. Among them, cyano- and N,N-dimethylamino-substituted 8-naphthylethynylated 2'-deoxyadenosine derivatives ((cn)A and (dn)A) showed strong fluorescence with high quantum yields and a remarkable solvatofuorochromicity. In particular, fluorescence of N,N-dimethylamino-substituted (2,6dn)A was not quenched by neighboring guanines (Gs) when incorporated in DNA duplexes, in contrast to (cn)A. We developed a new fluorescent probe containing (2,6dn)A that can be used for the detection of target DNA via a bulge formation regardless of the neighboring sequences. (c) 2012 Elsevier Ltd. All rights reserved.