4-[N-(p-phenyl)-4-nitro-1,8-napthalimide]-2,2'-bipyridine | 1004994-31-3

• 分子结构分类: 有机化合物 - 苯类化合物 - 萘
• 英文名称: 4-[N-(p-phenyl)-4-nitro-1,8-napthalimide]-2,2'-bipyridine
• 英文别名: 6-Nitro-2-[4-(2-pyridin-2-ylpyridin-4-yl)phenyl]benzo[de]isoquinoline-1,3-dione；6-nitro-2-[4-(2-pyridin-2-ylpyridin-4-yl)phenyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1004994-31-3
• 化学式: C₂₈H₁₆N₄O₄
• 分子量: 472.459
• InChiKey: ANFZAQRFJXVVMJ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.7
• 重原子数：
  36
• 可旋转键数：
  3
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.0
• 拓扑面积：
  109
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  4-[N-(p-phenyl)-4-nitro-1,8-napthalimide]-2,2'-bipyridine 在 palladium 10% on activated carbon 、 一水合肼 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 反应 5.0h， 以94%的产率得到4-[N-(p-phenyl)-4-amino-1,8-napthalimide]-2,2'-bipyridine
  参考文献：
  名称：

  Photophysical and biological investigation of novel luminescent Ru(ii)-polypyridyl-1,8-naphthalimide Tröger's bases as cellular imaging agents

  摘要：

  描述了两种 Ru(II)-聚吡啶基 1,8-萘二甲酰亚胺 Tröger 碱 1 和 2 的合成和光物理性质；研究发现它们可以稳定双链 DNA，快速被细胞吸收，即使在孵育 24 小时后也能显示良好的发光而不影响细胞活力。

  DOI：

  10.1039/c2cc17274g
• 作为产物：
  描述：

  (E)-4-(4-nitro-phenyl)-2-oxo-3-butenoic acid 在 palladium 10% on activated carbon 、 ammonium acetate 作用下， 以 乙醇 、 水 为溶剂， 反应 55.0h， 生成 4-[N-(p-phenyl)-4-nitro-1,8-napthalimide]-2,2'-bipyridine
  参考文献：
  名称：

  Photophysical and biological investigation of novel luminescent Ru(ii)-polypyridyl-1,8-naphthalimide Tröger's bases as cellular imaging agents

  摘要：

  描述了两种 Ru(II)-聚吡啶基 1,8-萘二甲酰亚胺 Tröger 碱 1 和 2 的合成和光物理性质；研究发现它们可以稳定双链 DNA，快速被细胞吸收，即使在孵育 24 小时后也能显示良好的发光而不影响细胞活力。

  DOI：

  10.1039/c2cc17274g

文献信息

• Synthesis and photophysical evaluations of fluorescent quaternary bipyridyl-1,8-naphthalimide conjugates as nucleic acid targeting agents
  作者：Gary J. Ryan、Robert B.P. Elmes、Susan J. Quinn、Thorfinnur Gunnlaugsson

  DOI：10.1080/10610278.2011.638381

  日期：2012.3

  A family of organic molecules containing the DNA intercalating chromophores, 4-nitro- and 4-amino 1,8-naphthalimide, conjugated to a diquat derivative by an 'orthogonal' phenyl spacer have been prepared and characterised. Their binding interactions with double-stranded DNA were studied by a variety of spectroscopic techniques. These charged organic compounds are found to exhibit excellent binding affinities to DNA with binding constants comparable to those exhibited by metal complexes.
• Highly Effective DNA Photocleavage by Novel “Rigid” Ru(bpy)₃-4-nitro- and -4-amino-1,8-naphthalimide Conjugates
  作者：Gary J. Ryan、Susan Quinn、Thorfinnur Gunnlaugsson

  DOI：10.1021/ic700967y

  日期：2008.1.1

  The synthesis of the two novel 1,8-naphthalimideruthenium conjugates Ru-Nap-NO2 and Ru-Nap-NH2 and their photophysical evaluation upon interaction with DNA is reported. Significant changes were seen in both the absorption and emission spectra upon interaction of both conjugates with DNA, from which large binding constants were determined. Moreover, highly efficient DNA cleavage was observed upon irradiation for 5 min, during which supercoiled DNA was converted to nicked and linear DNA by RuNap-NH2.