4-morpholinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide | 1351811-22-7

• 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: 4-morpholinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide
• 英文别名: 6-(4-morpholinyl)-2-(2-propynyl)-1H-benzo[de]isoquinoline-1,3(2H)-dione；6-Morpholin-4-yl-2-prop-2-ynylbenzo[de]isoquinoline-1,3-dione
• CAS: 1351811-22-7
• 化学式: C₁₉H₁₆N₂O₃
• 分子量: 320.348
• InChiKey: HBHJXOHTBHUZMN-UHFFFAOYSA-N

物化性质

• 沸点：
  555.9±50.0 °C(Predicted)
• 密度：
  1.346±0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.26
• 拓扑面积：
  49.8
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  三苯基膦氯金 、 4-morpholinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 以87.4%的产率得到
  参考文献：
  名称：

  Alkynyl-naphthalimide Fluorophores: Gold Coordination Chemistry and Cellular Imaging Applications

  摘要：

  A range of fluorescent alkynyl-naphthalimide fluorophores has been synthesized and their photophysical properties examined. The fluorescent ligands are based upon a 4-substituted 1,8-naphthalimide core and incorporate structural variations (at the 4-position) to tune the amphiphilic character: chloro (L1), 4-[2-(2-aminoethoxy)ethanol] (L2), 4-[2-(2-methoxyethoxy)ethylamino] (L3), piperidine (L4), morpholine (L5), 4-methylpiperidine (1,6), and 4-piperidone ethylene ketal (L7) variants: The amino-substituted species (L2 L7), are fluorescent in the visible region at around 517 535 inn through a naphthalimide-localized intramolecular charge transfer (ICT), with appreciable Stokes shifts of ca. 6500 cm(-1) and lifetimes up to 10.4 ns. Corresponding two-coordinate Au(I) complexes [Au(L)(PPh3)] were isolated, with X-ray structural studies revealing the expected coordination mode via the alkyne donor. The Au(I) complexes retain the visible fluorescence associated with the coordinated alkynyl-naphthalimide ligand. The ligands and complexes were investigated for their cytotoxicity across a range of cell lines (LOVO, MCF-7, A549, PC3, HEK) and their potential as cell imaging agents for HEK (human embryonic kidney) cells and Spironucleus vortens using confocal fluorescence microscopy. The images reveal that these fluorophores are highly compatible with fluorescence microscopy and show some clear intracellular localization patterns that are dependent upon the specific nature of the naphthalimide substituent.

  DOI：

  10.1021/acs.inorgchem.5b00954
• 作为产物：
  描述：

  4-氯-1,8-萘二甲酸酐 以 乙醇 、 二甲基亚砜 为溶剂， 反应 24.0h， 生成 4-morpholinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide
  参考文献：
  名称：

  Alkynyl-naphthalimide Fluorophores: Gold Coordination Chemistry and Cellular Imaging Applications

  摘要：

  A range of fluorescent alkynyl-naphthalimide fluorophores has been synthesized and their photophysical properties examined. The fluorescent ligands are based upon a 4-substituted 1,8-naphthalimide core and incorporate structural variations (at the 4-position) to tune the amphiphilic character: chloro (L1), 4-[2-(2-aminoethoxy)ethanol] (L2), 4-[2-(2-methoxyethoxy)ethylamino] (L3), piperidine (L4), morpholine (L5), 4-methylpiperidine (1,6), and 4-piperidone ethylene ketal (L7) variants: The amino-substituted species (L2 L7), are fluorescent in the visible region at around 517 535 inn through a naphthalimide-localized intramolecular charge transfer (ICT), with appreciable Stokes shifts of ca. 6500 cm(-1) and lifetimes up to 10.4 ns. Corresponding two-coordinate Au(I) complexes [Au(L)(PPh3)] were isolated, with X-ray structural studies revealing the expected coordination mode via the alkyne donor. The Au(I) complexes retain the visible fluorescence associated with the coordinated alkynyl-naphthalimide ligand. The ligands and complexes were investigated for their cytotoxicity across a range of cell lines (LOVO, MCF-7, A549, PC3, HEK) and their potential as cell imaging agents for HEK (human embryonic kidney) cells and Spironucleus vortens using confocal fluorescence microscopy. The images reveal that these fluorophores are highly compatible with fluorescence microscopy and show some clear intracellular localization patterns that are dependent upon the specific nature of the naphthalimide substituent.

  DOI：

  10.1021/acs.inorgchem.5b00954

文献信息

• Synthesis, Optimization, and Evaluation of Glycosylated Naphthalimide Derivatives as Efficient and Selective Insect β-<i>N</i>-Acetylhexosaminidase OfHex1 Inhibitors
  作者：Shengqiang Shen、Lili Dong、Wei Chen、Renjie Wu、Huizhe Lu、Qing Yang、Jianjun Zhang

  DOI：10.1021/acs.jafc.9b02281

  日期：2019.6.5

  optimization led to the synthesis of compounds 15r (Ki = 5.3 μM) and 15y (Ki = 2.7 μM) that had superior activity against OfHex1 than previously reported lead compounds. Both compounds 15r and 15y had high selectivity toward OfHex1 over human β-N-acetylhexosaminidase B (HsHexB) and human O-GlcNAcase (hOGA). In addition, to investigate the basis for the potency of glycosylated naphthalimides against

  昆虫几丁质β- ñ -acetylhexosaminidase OfHex1，从农业害虫玉米螟（螟），被认为是绿色农药设计的潜在目标。在这项研究中，合理的分子设计和优化导致了合成15r（K i = 5.3μM ）和15y（K i = 2.7μM）的化合物，它们对OfHex1的活性优于先前报道的先导化合物。化合物15r和15y对OfHex1的选择性都高于人β- N-乙酰基己糖胺酶B（HsHexB）和人O-GlcNAcase（hOGA）。此外，为了研究糖基化萘二甲酰亚胺对OfHex1效力的基础，进行了分子对接和分子动力学模拟，以研究可能的结合模式。此外，在体内高效OfHex1抑制效力目标化合物的生物活性进行测定对桃蚜，小菜蛾，和亚洲玉米螟。这项工作表明，糖基化萘二甲酰亚胺可以进一步开发为针对OfHex1的潜在害虫控制和管理剂。
• Modular Construction of Fluorescent Lipophosphoramidates by Click Chemistry
  作者：Mathieu Berchel、Jean-Pierre Haelters、Hélène Couthon-Gourvès、Laure Deschamps、Patrick Midoux、Pierre Lehn、Paul-Alain Jaffrès

  DOI：10.1002/ejoc.201100900

  日期：2011.11

  The synthesis of fluorescent lipophosphoramidates is reported. Their modular construction allows several variations of the molecular structure including the separation of the fluorescent probe from the lipophosphoramidate moiety by a short methylene or by a tetraethylene glycol spacer. The last step of the convergent synthesis is a Huisgen click reaction, which assembles the fluorescent probe with

  报道了荧光脂磷酰胺的合成。它们的模块化结构允许分子结构的多种变化，包括通过短亚甲基或四甘醇间隔物将荧光探针与脂磷酰胺部分分离。收敛合成的最后一步是 Huisgen 点击反应，它将荧光探针与 lipophosphoramidate 部分组装起来。本研究考虑了五种荧光探针，包括香豆素、NBD、荧光素、萘二甲酰亚胺和花青。
• Functionalized Phospholipid Molecular Platform: Use for Production of Cationic Fluorescent Lipids
  作者：Mathieu Berchel、Jean-Pierre Haelters、Damien Afonso、Alicia Maroto、Laure Deschamps、Philippe Giamarchi、Paul-Alain Jaffrès

  DOI：10.1002/ejoc.201301416

  日期：2014.2

  Fluorescent amphiphilic phospholipids (neutral or cationic) in which fluorescent probes are contained in the lipid domain were synthesized via phosphoramide intermediates possessing two distinct lipid chains. One of these lipid chains is ω-functionalized with an azide or alkyne group, and this is subsequently used to introduce a fluorescent probe by Huisgen cycloaddition. Five different fluorescent

  荧光两亲性磷脂（中性或阳离子），其中荧光探针包含在脂质域中，是通过具有两个不同脂质链的磷酰胺中间体合成的。这些脂质链之一用叠氮化物或炔烃基团进行 ω 功能化，随后通过 Huisgen 环加成作用引入荧光探针。本研究考虑了五种不同的荧光探针（萘二甲酰亚胺、丹磺酰、荧光素、尼罗红和香豆素）。这些中性和阳离子荧光脂质与选定的阳离子脂质 (KLN47) 以 1% 的摩尔比加入，以产生通过动态光散射和 zeta 电位测量表征的脂质体溶液。
• A bis-spiropyran-containing multi-state [2]rotaxane with fluorescence output
  作者：Wei Zhou、Hui Zhang、Hong Li、Yu Zhang、Qiao-Chun Wang、Da-Hui Qu

  DOI：10.1016/j.tet.2013.04.119

  日期：2013.7

  ized [2]rotaxane with a 4-morpholin-naphthalimide fluorophore as stopper was designed, synthesized, and studied. The macrocycle can shuttle reversibly in response to external acid–base stimuli and the spiropyran functional group can be switched to its ring-opened merocyanine (MC) state. It has been shown that, by introducing two spiropyran units into the system, intercomponent interactions, such as

  本文设计，合成和研究了以4-吗啉-萘二甲酰亚胺荧光团为阻滞剂的双螺并吡喃官能化的[2]轮烷。大环化合物可响应外部酸碱刺激而可逆穿梭，并且螺吡喃官能团可切换至其开环的花菁（MC）状态。研究表明，通过将两个螺吡喃单元引入系统中，SP或MC功能单元与荧光团之间的组分间相互作用（例如电子转移和能量转移过程）可以响应于酸碱的结合而发生变化。和光化学刺激，可以产生明显的紫外线/可见光吸收和荧光光谱变化。
• A fluorescent bistable [2]rotaxane molecular switch on SiO₂ nanoparticles
  作者：Zhan-Qi Cao、Qi Miao、Qi Zhang、Hong Li、Da-Hui Qu、He Tian

  DOI：10.1039/c4cc09976a

  日期：——

  A fluorescent bistable [2]rotaxane terminated with an alkyne functional group was constructed and immobilized onto the surface of SiO2 nanoparticles through click reaction. The shuttling motion of the macrocycle component between two different stations was driven by external acid-base stimuli both in solution and on SiO2 nanoparticles, accompanied by visual fluorescence changes.

  构建了带有炔官能团的荧光双稳态[2]轮烷，并通过点击反应将其固定在SiO2纳米颗粒的表面上。大环组分在两个不同工位之间的穿梭运动是由溶液中和SiO2纳米颗粒上的外部酸碱刺激驱动的，同时伴随着可见的荧光变化。