N(9)-[2-(4-methyl-piperazino)-ethyl]-4-amino-1,8-naphthalimide | 1185993-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 异喹啉及其衍生物
• 英文名称: N(9)-[2-(4-methyl-piperazino)-ethyl]-4-amino-1,8-naphthalimide
• 英文别名: N-(1-methylpyprazinoethyl)-4-amino-1,8-naphthalimide；6-Amino-2-[2-(4-methylpiperazin-1-yl)ethyl]benzo[de]isoquinoline-1,3-dione
• CAS: 1185993-21-8
• 化学式: C₁₉H₂₂N₄O₂
• 分子量: 338.409
• InChiKey: DUBJWGTUZWLICE-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.3
• 重原子数：
  25
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  69.9
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  聚合甲醛 、 N(9)-[2-(4-methyl-piperazino)-ethyl]-4-amino-1,8-naphthalimide 在 三氟乙酸 、 sodium hydroxide 作用下， 以 水 为溶剂， 反应 12.0h， 以50%的产率得到bis-{N-[2-(4-methyl-piperazino)-ethyl]}-9,18-methano-1,8-naphthalimido[b,f][1,5]-diazocine
  参考文献：
  名称：

  4-Amino-1,8-naphthalimide-Based Tröger’s Bases As High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds

  摘要：

  The synthesis and photophysical and biological Investigation of fluorescent 1,8-naphthalimide conjugated Troger's bases 1-3 are described. These structures bind strongly to DNA in competitive media at pH 7.4, with concomitant modulation in their fluorescence emission. These structures also undergo rapid cellular uptake, being localized within the nucleus within a few hours, and are cytotoxic against HL60 and (chronic myeloid leukemia) K562 cell lines.

  DOI：

  10.1021/ol9013602
• 作为产物：
  描述：

  N-[2-(4-methyl-piperazino)-ethyl]-4-nitro-1,8-naphthalimide 在 palladium 10% on activated carbon 、 氢气 作用下， 以 甲醇 为溶剂， 以98%的产率得到N(9)-[2-(4-methyl-piperazino)-ethyl]-4-amino-1,8-naphthalimide
  参考文献：
  名称：

  4-Amino-1,8-naphthalimide-Based Tröger’s Bases As High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds

  摘要：

  The synthesis and photophysical and biological Investigation of fluorescent 1,8-naphthalimide conjugated Troger's bases 1-3 are described. These structures bind strongly to DNA in competitive media at pH 7.4, with concomitant modulation in their fluorescence emission. These structures also undergo rapid cellular uptake, being localized within the nucleus within a few hours, and are cytotoxic against HL60 and (chronic myeloid leukemia) K562 cell lines.

  DOI：

  10.1021/ol9013602

文献信息

• 4-Amino-1,8-naphthalimide-Based Tröger’s Bases As High Affinity DNA Targeting Fluorescent Supramolecular Scaffolds
  作者：Emma B. Veale、Daniel O. Frimannsson、Mark Lawler、Thorfinnur Gunnlaugsson

  DOI：10.1021/ol9013602

  日期：2009.9.17

  The synthesis and photophysical and biological Investigation of fluorescent 1,8-naphthalimide conjugated Troger's bases 1-3 are described. These structures bind strongly to DNA in competitive media at pH 7.4, with concomitant modulation in their fluorescence emission. These structures also undergo rapid cellular uptake, being localized within the nucleus within a few hours, and are cytotoxic against HL60 and (chronic myeloid leukemia) K562 cell lines.
• Synthesis, Photophysical, and DNA Binding Studies of Fluorescent Tröger’s Base Derived 4-Amino-1,8-naphthalimide Supramolecular Clefts
  作者：Emma B. Veale、Thorfinnur Gunnlaugsson

  DOI：10.1021/jo1005697

  日期：2010.8.20

  The synthesis and characterization of three bis-1,8-naphthalimide-containing Trager's bases 1-3, formed from the corresponding 4-amino-1,8-naphthalimide precursors 7-9 in a single step, is described. The photophysical investigation of 1-3 and 7-9 was carried out in various organic solvents as well as in water and as a function of pH using UV/vis and fluorescence spectroscopy. As for their 4-amino-1,8-naphthalimide precursors 7-9, both the ground-state and excited-state characteristics of 1-3 were dependent on the polarity and the hydrogen-bonding ability of the solvent medium. The DNA-binding affinities of 1-3 were also studied in aqueous solution at pH 7.4, in the presence of calf-thymus DNA (ct-DNA), using various UV/vis absorption and fluorescence spectroscopic methods. These molecules exhibited significant DNA-binding ability, where large binding values K-b in the range of 10(6) M-1 were determined. Such strong binding to ct-DNA was maintained even in competitive media (50 and 160 mM NaCl) and was also found to be irreversible regardless of the concentration of the ionic strength. Thermal denaturation experiments also demonstrated that the interaction of 1-3 with ct-DNA gave rise to significant stabilization in the double-helical structure of DNA. The binding affinity of 1-3 for ct-DNA was also compared to that of their 4-amino-1,8-naphthalimide precursors 7-9, determined by fitting of data using "intrinsic" methods and ethidium bromide displacement assays. The latter method Oyes outstanding binding constants for 1-3 in the range of 10(7) M-1.