2,5-dioxopyrrolidin-1-yl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxylate | 150321-91-8

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 香豆素及其衍生物
• 英文名称: 2,5-dioxopyrrolidin-1-yl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxylate
• 英文别名: (2,5-Dioxopyrrolidin-1-yl) 4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carboxylate
• CAS: 150321-91-8
• 化学式: C₂₀H₁₈N₂O₆
• 分子量: 382.373
• InChiKey: ZLKDVLWHTPNEHU-UHFFFAOYSA-N

物化性质

• 沸点：
  650.7±65.0 °C(Predicted)
• 密度：
  1.54±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  28
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  93.2
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  2,5-dioxopyrrolidin-1-yl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxylate 在 吗啉 、 N-甲基吗啉 、 4-二甲氨基吡啶 、 2-氯-4,6-二甲氧基-1,3,5-三嗪 、 碳酸氢钠 、 N,N'-二环己基碳二亚胺 作用下， 以 四氢呋喃 、 氯仿 、 水 、 N,N-二甲基甲酰胺 为溶剂， 反应 29.25h， 生成 2-(trimethylsilyl)ethyl N6-(11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carbonyl)-N2-((2-(3-oxo-2-(pent-2-en-1-yl)cyclopentyl)acetyl)-L-isoleucyl)-L-lysinate
  参考文献：
  名称：

  Rational design and efficient synthesis of a fluorescent-labeled jasmonate

  摘要：

  A fluorescent-labeled jasmonate was rationally designed based on examination of the model of interaction between the jasmonate and its receptor. An efficient synthetic route has been developed for this molecule. The biological activity of this fluorescent probe was retained which was similar to that of the methyl jasmonate as examined by root growth inhibition bioassay. This fluorescent probe will greatly facilitate biological studies of jasmonates through fluorescent imaging. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.006
• 作为产物：
  描述：

  香豆素343甲酯 在 吡啶 、 盐酸 、 草酰氯 、 N,N-二甲基甲酰胺 作用下， 以 氯仿 、 水 为溶剂， 反应 25.0h， 生成 2,5-dioxopyrrolidin-1-yl 11-oxo-2,3,6,7-tetrahydro-1H,5H,11H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10-carboxylate
  参考文献：
  名称：

  Rational design and efficient synthesis of a fluorescent-labeled jasmonate

  摘要：

  A fluorescent-labeled jasmonate was rationally designed based on examination of the model of interaction between the jasmonate and its receptor. An efficient synthetic route has been developed for this molecule. The biological activity of this fluorescent probe was retained which was similar to that of the methyl jasmonate as examined by root growth inhibition bioassay. This fluorescent probe will greatly facilitate biological studies of jasmonates through fluorescent imaging. (C) 2012 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2012.06.006

文献信息

• Topology-Selective, Fluorescent “Light-Up” Probes for G-Quadruplex DNA Based on Photoinduced Electron Transfer
  作者：Xiao Xie、Oksana Reznichenko、Ludovic Chaput、Pascal Martin、Marie-Paule Teulade-Fichou、Anton Granzhan

  DOI：10.1002/chem.201801701

  日期：2018.8.27

  Six novel probes were prepared by covalent attachment of a G4‐DNA ligand (bis(quinolinium) pyridodicarboxamide; PDC) to various coumarin or pyrene fluorophores. In the absence of DNA, the fluorescence of all probes is quenched due to intramolecular photoinduced electron transfer (PET), as evidenced by photophysical and electrochemical studies, molecular modeling, and DFT calculations. All probes demonstrate

  通过将G4-DNA配体（双（喹啉鎓）吡啶二甲酰胺; PDC）共价连接到各种香豆素或pyr荧光基团上制备了六种新颖的探针。在不存在DNA的情况下，由于分子内的光诱导电子转移（PET），所有探针的荧光都被淬灭，这一点已通过光物理和电化学研究，分子建模和DFT计算得到了证明。所有探针均显示出不同的G4-DNA底物具有相似的高热稳定性，这些底物属于不同的折叠拓扑结构，这是通过荧光熔解实验评估得出的；但是，它们的荧光响应在探针和G4-DNA靶标的结构上是高度异质的。因此，在存在G4-DNA的情况下，含有7-二乙基氨基香豆素荧光团的探针显示出显着的荧光增强，对反平行G4结构以及由人端粒序列变体形成的杂合G4结构观察到最强的“亮起”响应（20到180倍），并且能够构象改变为反平行同种型。这些结果揭示了荧光团的接头和电子性质对通过PET操作的G4-DNA“发光”探针效率的影响。
• Fluorescently Labeled Amino Acids as Building Blocks for Bioactive Molecules
  作者：Michael Gütschow、Daniela Häußler

  DOI：10.1055/s-0035-1560361

  日期：——

  A series of twelve fluorescently labeled amino acids were designed by assembling different coumarin, fluorescein, or nitrobenzofurazan fluorophores with N-protected lysine or 2-aminopropionic acid. The synthesized amino acids were evaluated with regard to their spectroscopic properties. The easy introduction of the amino acids into peptides and peptidomimetics was exemplarily shown for one coumarin-labeled amino acid.
• NANOLUC SUICIDE SUBSTRATES
  申请人：PROMEGA CORPORATION

  公开号：US20190337939A1

  公开（公告）日：2019-11-07

  Compounds that may inhibit Oplophorus -derived luciferases are disclosed as well as compositions and kits comprising the compounds and methods of using the compounds.