4-(4-N,N-dimethylaminophenylethynyl)-N-(2-propynyl)-1,8-naphthalimide | 1416252-45-3

• 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-(4-N,N-dimethylaminophenylethynyl)-N-(2-propynyl)-1,8-naphthalimide
• 英文别名: 6-[2-[4-(Dimethylamino)phenyl]ethynyl]-2-prop-2-ynylbenzo[de]isoquinoline-1,3-dione；6-[2-[4-(dimethylamino)phenyl]ethynyl]-2-prop-2-ynylbenzo[de]isoquinoline-1,3-dione
• CAS: 1416252-45-3
• 化学式: C₂₅H₁₈N₂O₂
• 分子量: 378.43
• InChiKey: PSJFAKCMFNYJIY-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.4
• 重原子数：
  29
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.12
• 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：

  4-(4-N,N-dimethylaminophenylethynyl)-N-(2-propynyl)-1,8-naphthalimide 、 (S)-tert-butyl (3-azido-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate 在 copper(II) sulfate 、 sodium ascorbate 、 N,N-二异丙基乙胺 作用下， 以 四氢呋喃 、 水 为溶剂， 以74%的产率得到(S)-tert-butyl (3-(4-((6-((4-(dimethylamino)phenyl)ethynyl)-1,3-dioxo-1H-benzo[de]isoquinolin-2(3H)-yl)methyl)-1H-1,2,3-triazol-1-yl)-1-(methoxy(methyl)amino)-1-oxopropan-2-yl)carbamate
  参考文献：
  名称：

  三唑基供体/受体生色团的合成，光物理性质修饰了非天然氨基酸：在亮氨酸脑啡肽中引入一对，三唑基戊二烯氨基酸在传感BSA中的应用。

  摘要：

  在非天然氨基酸的设计和合成领域中的研究正在迅速发展，以增加对潜在治疗剂和许多其他多样化的新颖功能应用的蛋白质的需求。因此，我们在本文中报道了通过点击化学用供体和/或受体芳族发色团修饰的微环境敏感的荧光三唑基非天然氨基酸（UNAA）的设计和合成。合成的荧光氨基酸显示出有趣的溶剂变色特性和/或分子内电荷转移（ICT）特性，如从UV-可见光，荧光光物理特性和DFT / TDDFT计算中所揭示的那样。HOMO-LUMO分布表明，某些氨基酸的发射态在三唑基部分和与其相连的芳族发色团之间具有更显着的电子再分布特征，从而导致发射特性得到调节。一对供体-受体氨基酸显示出有趣的光物理相互作用特性，表明发生了FRET猝灭事件。此外，一种氨基酸三唑基-per氨基酸已被用于研究与BSA的相互作用，并发现它能够以增强的荧光强度来感测BSA。最后，我们将一对供体/受体氨基酸掺入Leu-脑啡肽类似物五肽中，发现其主要采用II型β-转角构象。

  DOI：

  10.1016/j.bmc.2016.05.069
• 作为产物：
  描述：

  4-(2-(4-(N,N-dimethylamino)phenyl)ethynyl)-1,8-naphthalic anhydride 、 炔丙胺 以 乙醇 为溶剂， 以63%的产率得到4-(4-N,N-dimethylaminophenylethynyl)-N-(2-propynyl)-1,8-naphthalimide
  参考文献：
  名称：

  Highly solvatochromic fluorescent naphthalimides: Design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA

  摘要：

  We report the design, synthesis and photophysical properties of highly solvatochromic donor/acceptor substituted naphthalimide based fluorophores. The synthesized naphthalimides containing propargyl ends showed highly solvatochromic intramolecular charge transfer (ICT) feature as was revealed from the UV-visible, fluorescence photophysical properties of these fluorophores and DFT/TDDFT calculation. Fluorescence life times for the imide fluorophores were also measured in different solvents. The solid state photophysical property of donor substituted naphthalimide 1 showed promising for future application in material sciences. Furthermore, both the donor/acceptor substituted naphthalimide fluorophores 1-2 were exploited in sensing calf-thymus DNA via switch-on fluorescence response. The propargyl linker containing naphthalimides can further be exploited for the synthesis of labeled biomolecular building blocks. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2012.11.003

文献信息

• Synthesis, photophysical properties of triazolyl-donor/acceptor chromophores decorated unnatural amino acids: Incorporation of a pair into Leu-enkephalin peptide and application of triazolylperylene amino acid in sensing BSA
  作者：Subhendu Sekhar Bag、Subhashis Jana、Manoj Kumar Pradhan

  DOI：10.1016/j.bmc.2016.05.069

  日期：2016.8

  The research in the field of design and synthesis of unnatural amino acids is growing at a fast space for the increasing demand of proteins of potential therapeutics and many other diversified novel functional applications. Thus, we report herein the design and synthesis of microenvironment sensitive fluorescent triazolyl unnatural amino acids (UNAA) decorated with donor and/or acceptor aromatic chromophores

  在非天然氨基酸的设计和合成领域中的研究正在迅速发展，以增加对潜在治疗剂和许多其他多样化的新颖功能应用的蛋白质的需求。因此，我们在本文中报道了通过点击化学用供体和/或受体芳族发色团修饰的微环境敏感的荧光三唑基非天然氨基酸（UNAA）的设计和合成。合成的荧光氨基酸显示出有趣的溶剂变色特性和/或分子内电荷转移（ICT）特性，如从UV-可见光，荧光光物理特性和DFT / TDDFT计算中所揭示的那样。HOMO-LUMO分布表明，某些氨基酸的发射态在三唑基部分和与其相连的芳族发色团之间具有更显着的电子再分布特征，从而导致发射特性得到调节。一对供体-受体氨基酸显示出有趣的光物理相互作用特性，表明发生了FRET猝灭事件。此外，一种氨基酸三唑基-per氨基酸已被用于研究与BSA的相互作用，并发现它能够以增强的荧光强度来感测BSA。最后，我们将一对供体/受体氨基酸掺入Leu-脑啡肽类似物五肽中，发现其主要采用II型β-转角构象。
• Highly solvatochromic fluorescent naphthalimides: Design, synthesis, photophysical properties and fluorescence switch-on sensing of ct-DNA
  作者：Subhendu Sekhar Bag、Manoj Kumar Pradhan、Rajen Kundu、Subhashis Jana

  DOI：10.1016/j.bmcl.2012.11.003

  日期：2013.1

  We report the design, synthesis and photophysical properties of highly solvatochromic donor/acceptor substituted naphthalimide based fluorophores. The synthesized naphthalimides containing propargyl ends showed highly solvatochromic intramolecular charge transfer (ICT) feature as was revealed from the UV-visible, fluorescence photophysical properties of these fluorophores and DFT/TDDFT calculation. Fluorescence life times for the imide fluorophores were also measured in different solvents. The solid state photophysical property of donor substituted naphthalimide 1 showed promising for future application in material sciences. Furthermore, both the donor/acceptor substituted naphthalimide fluorophores 1-2 were exploited in sensing calf-thymus DNA via switch-on fluorescence response. The propargyl linker containing naphthalimides can further be exploited for the synthesis of labeled biomolecular building blocks. (C) 2012 Elsevier Ltd. All rights reserved.