5,8-diamino-2-(3-morpholinopropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione | 107107-76-6

• 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: 5,8-diamino-2-(3-morpholinopropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
• 英文别名: 5,8-Diamino-2-(3-morpholin-4-ylpropyl)benzo[de]isoquinoline-1,3-dione
• CAS: 107107-76-6
• 化学式: C₁₉H₂₂N₄O₃
• 分子量: 354.409
• InChiKey: RVQAXPDPSUNZDZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  26
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.37
• 拓扑面积：
  102
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  5,8-diamino-2-(3-morpholinopropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione 在 sodium iodide 作用下， 以 乙醇 为溶剂， 反应 5.0h， 生成 N,N'-(2-(3-morpholinopropyl)-1,3-dioxo-2,3-dihydro-1H-benzo[de]isoquinoline-5,8-diyl)bis(3-(pyrrolidin-1-yl)propanamide)
  参考文献：
  名称：

  Design, synthesis, biophysical and biological studies of trisubstituted naphthalimides as G-quadruplex ligands

  摘要：

  A series of trisubstituted naphthalimides have been synthesized and evaluated as telomeric G-quadruplex ligands by biophysical methods. Affinity for telomeric G-quadruplex AGGG(TTAGGG)(3) binding was first screened by fluorescence titrations. Subsequently, the interaction of the telomeric G-quadruplex with compounds showing the best affinity has been studied by isothermal titration calorimetry and UV-melting experiments. The two best compounds of the series tightly bind the telomeric quadruplex with a 2:1 drug/DNA stoichiometry. These derivatives have been further evaluated for their ability to inhibit telomerase by a TRAP assay and their pharmacological properties by treating melanoma (M14) and human lung cancer (A549) cell lines with increasing drug concentrations. A dose-dependent inhibition of cell proliferation was observed for all cellular lines during short-term treatment. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmc.2011.08.062
• 作为产物：
  描述：

  2-(3-Morpholin-4-ylpropyl)-5,8-dinitrobenzo[de]isoquinoline-1,3-dione 在 palladium on activated charcoal 氢气 作用下， 以 乙醇 为溶剂， 反应 17.0h， 以68%的产率得到5,8-diamino-2-(3-morpholinopropyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione
  参考文献：
  名称：

  Synthesis and fluorescence ofN-substituted-1,8-naphthalimides

  摘要：

  AbstractA number of novel N‐substituted‐1,8‐naphthalimides have been prepared and their fluorescence yields measured in water at pH 7.4. The type of substitutent and the substitution pattern on the naphthalimide nucleus produce markedly different fluorescence yields, (quantum efficiencies, ø varying from ø = 0‐0037 for N‐(3‐N'‐morpholino‐1‐propyl)‐4‐amino‐3‐methoxy‐1,8‐naphthalirnide (7) to ø = 0–77 for N‐(3‐bromopropyl)‐4‐acetamido‐1,8‐naphthalimide (31).

  DOI：

  10.1002/jhet.5570230337

文献信息

• Design, synthesis, biophysical and biological studies of trisubstituted naphthalimides as G-quadruplex ligands
  作者：Antonella Peduto、Bruno Pagano、Carmen Petronzi、Antonio Massa、Veronica Esposito、Antonella Virgilio、Francesco Paduano、Francesco Trapasso、Filomena Fiorito、Salvatore Florio、Concetta Giancola、Aldo Galeone、Rosanna Filosa

  DOI：10.1016/j.bmc.2011.08.062

  日期：2011.11

  A series of trisubstituted naphthalimides have been synthesized and evaluated as telomeric G-quadruplex ligands by biophysical methods. Affinity for telomeric G-quadruplex AGGG(TTAGGG)(3) binding was first screened by fluorescence titrations. Subsequently, the interaction of the telomeric G-quadruplex with compounds showing the best affinity has been studied by isothermal titration calorimetry and UV-melting experiments. The two best compounds of the series tightly bind the telomeric quadruplex with a 2:1 drug/DNA stoichiometry. These derivatives have been further evaluated for their ability to inhibit telomerase by a TRAP assay and their pharmacological properties by treating melanoma (M14) and human lung cancer (A549) cell lines with increasing drug concentrations. A dose-dependent inhibition of cell proliferation was observed for all cellular lines during short-term treatment. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis and fluorescence of<i>N</i>-substituted-1,8-naphthalimides
  作者：Richard W. Middleton、John Parrick、Eric D. Clarke、Peter Wardman

  DOI：10.1002/jhet.5570230337

  日期：1986.5

  AbstractA number of novel N‐substituted‐1,8‐naphthalimides have been prepared and their fluorescence yields measured in water at pH 7.4. The type of substitutent and the substitution pattern on the naphthalimide nucleus produce markedly different fluorescence yields, (quantum efficiencies, ø varying from ø = 0‐0037 for N‐(3‐N'‐morpholino‐1‐propyl)‐4‐amino‐3‐methoxy‐1,8‐naphthalirnide (7) to ø = 0–77 for N‐(3‐bromopropyl)‐4‐acetamido‐1,8‐naphthalimide (31).