4-piperidinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide

• 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-piperidinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide
• 英文别名: 6-(piperidin-1-yl)-2-(prop-2-yn-1-yl)-1H-benzo[de]isoquinoline-1,3(2H)-dione；6-Piperidin-1-yl-2-prop-2-ynylbenzo[de]isoquinoline-1,3-dione；6-piperidin-1-yl-2-prop-2-ynylbenzo[de]isoquinoline-1,3-dione
• 化学式: C₂₀H₁₈N₂O₂
• 分子量: 318.375
• InChiKey: NRHRKJHRGQXTPZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.2
• 重原子数：
  24
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.3
• 拓扑面积：
  40.6
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  三苯基膦氯金 、 4-piperidinyl-(N-(2-propyn-1-yl))-1,8-naphthalimide 在 potassium tert-butylate 作用下， 以 乙醇 为溶剂， 以45%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-piperidinyl-(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。
• Organic Fluorophore Coated Polycrystalline Ceramic LSO:Ce Scintillators for X-ray Bioimaging
  作者：Mary K. Burdette、Yuriy P. Bandera、Eric Zhang、Artem Trofimov、Ashley Dickey、Isabell Foulger、Joseph W. Kolis、Kelli E. Cannon、Aundrea F. Bartley、Lynn E. Dobrunz、Mark S. Bolding、Lori McMahon、Stephen H. Foulger

  DOI：10.1021/acs.langmuir.8b03129

  日期：2019.1.8

  The current effort demonstrates that lutetium oxyorthosilicate doped with 1-10% cerium (Lu2SiO5:Ce, LSO:Ce) radioluminescent particles can be coated with a single dye or multiple dyes and generate an effective energy transfer between the core and dye(s) when excited via X-rays. LSO:Ce particles were surface modified with an alkyne modified naphthalimide (6-piperidin-1-yl-2-prop-2-yn-1-yl-1H-benzo[de]isoquinoline-1,3-(2H)-dione, AlNap) and alkyne modified rhodamine B (N-(6-diethylamino)-9-2-[(prop-2-yn-1-yloxy)carbonyl]phenyl}-3H-xanthen-3-ylidene)-N-ethylethanaminium, AlRhod) derivatives to tune the X-ray excited optical luminescence from blue to green to red using Forster Resonance Energy Transfer (FRET). As X-rays penetrate tissue much more effectively than UV/visible light, the fluorophore modified phosphors may have applications as bioimaging agents. To that end, the phosphors were incubated with rat cortical neurons and imaged after 24 h. The LSO:Ce surface modified with AlNap was able to be successfully imaged in vitro with a low-output X-ray tube. To use the LSO:Ce fluorophore modified particles as imaging agents, they must not induce cytotoxicity. Neither LSO:Ce nor LSO:Ce modified with AlNap showed any cytotoxicity toward normal human dermal fibroblast cells or mouse cortical neurons, respectively.