methyl 4-nitro-1-(4-pyrenylbutyl)pyrrole-2-carboxylate | 959127-77-6

• 分子结构分类: 有机化合物 - 苯类化合物 - 芘
• 英文名称: methyl 4-nitro-1-(4-pyrenylbutyl)pyrrole-2-carboxylate
• CAS: 959127-77-6
• 化学式: C₂₆H₂₂N₂O₄
• 分子量: 426.472
• InChiKey: LIOBUWRWKZXQQL-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.1
• 重原子数：
  32.0
• 可旋转键数：
  7.0
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.19
• 拓扑面积：
  74.37
• 氢给体数：
  0.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  methyl 4-nitro-1-(4-pyrenylbutyl)pyrrole-2-carboxylate 、 二碳酸二叔丁酯 在 palladium on activated charcoal 氢气 、 N,N-二异丙基乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 生成
  参考文献：
  名称：

  Detection of CAG repeat DNA sequences by pyrene-functionalized pyrrole-imidazole polyamides

  摘要：

  Five N-methylpyrrole-N-methylimidazole (Py-Im) polyamides possessing a fluorescent pyrene were synthesized by Fmoc solid-phase synthesis using Py/Im monomers and pyrenylbutyl-pyrrole monomer compound 9. The steady state fluorescence of conjugates 1-5 was examined in the presence and absence of (CAG)(12)-containing oligodeoxynucleotides (ODNs) 1 and 2. Of the conjugates, conjugate I showed no background emission around 470 nm in the absence of ODNs, and a clear increase of emission at 475 run was observed upon addition of ODNs I and 2. The emission of conjugate I at 475 nm increased linearly with the concentration of ODN and the number of CAG repeats. The results indicate that conjugate I efficiently forms a pyrene excimer upon binding in the minor groove of DNA. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.055
• 作为产物：
  描述：

  4-硝基-1H-吡咯-2-甲酸甲酯 、 1-(4-溴丁基)芘 在 四丁基碘化铵 、 potassium carbonate 作用下， 以 丙酮 为溶剂， 反应 11.0h， 以94%的产率得到methyl 4-nitro-1-(4-pyrenylbutyl)pyrrole-2-carboxylate
  参考文献：
  名称：

  Detection of CAG repeat DNA sequences by pyrene-functionalized pyrrole-imidazole polyamides

  摘要：

  Five N-methylpyrrole-N-methylimidazole (Py-Im) polyamides possessing a fluorescent pyrene were synthesized by Fmoc solid-phase synthesis using Py/Im monomers and pyrenylbutyl-pyrrole monomer compound 9. The steady state fluorescence of conjugates 1-5 was examined in the presence and absence of (CAG)(12)-containing oligodeoxynucleotides (ODNs) 1 and 2. Of the conjugates, conjugate I showed no background emission around 470 nm in the absence of ODNs, and a clear increase of emission at 475 run was observed upon addition of ODNs I and 2. The emission of conjugate I at 475 nm increased linearly with the concentration of ODN and the number of CAG repeats. The results indicate that conjugate I efficiently forms a pyrene excimer upon binding in the minor groove of DNA. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2007.07.055