7-diethylamino-3-(4-aminophenyl) coumarin | 131788-68-6

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 异黄酮类化合物
• 英文名称: 7-diethylamino-3-(4-aminophenyl) coumarin
• 英文别名: 3-(4-Aminophenyl)-7-(diethylamino)-2H-1-benzopyran-2-one；3-(4-aminophenyl)-7-(diethylamino)chromen-2-one
• CAS: 131788-68-6
• 化学式: C₁₉H₂₀N₂O₂
• 分子量: 308.38
• InChiKey: XTMYMVIAYRSVIG-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.21
• 拓扑面积：
  55.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  2,4-二硝基苯磺酰氯 、 7-diethylamino-3-(4-aminophenyl) coumarin 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以40%的产率得到N-(4-(7-diethylamino-2-oxo-2H-chromen-3-yl)phenyl)-2,4-dinitrobenzenesulfonamide
  参考文献：
  名称：

  Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications

  摘要：

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo

  DOI：

  10.1021/ja5099676
• 作为产物：
  描述：

  对硝基苯乙腈 在 哌啶 、 盐酸 、 tin(II) chloride dihdyrate 、 水 作用下， 以 乙醇 为溶剂， 反应 6.0h， 生成 7-diethylamino-3-(4-aminophenyl) coumarin
  参考文献：
  名称：

  Selective Selenol Fluorescent Probes: Design, Synthesis, Structural Determinants, and Biological Applications

  摘要：

  Selenium (Se) is an essential micronutrient element, and the biological significance of Se is predominantly dependent on its incorporation as selenocysteine (Sec), the genetically encoded 21st amino acid in protein synthesis, into the active site of selenoproteins, which have broad functions, ranging from redox regulation and anti-inflammation to the production of active thyroid hormones. Compared to its counterpart Cys, there are only limited probes for selective recognition of Sec, and such selectivity is strictly restricted at low pH conditions. We reported herein the design, synthesis, and biological evaluations of a series of potential Sec probes based on the mechanism of nucleophilic aromatic substitution. After the initial screening, the structural determinants for selective recognition of Sec were recapitulated. The follow-up studies identified that probe 19 (Sel-green) responds to Sec and other selenols with more than 100-fold increase of emission in neutral aqueous solution (pH 7.4), while there is no significant interference from the biological thiols, amines, or alcohols. Sel-green was successfully applied to quantify the Sec content in the selenoenzyme thioredoxin reductase and image endogenous Sec in live HepG2 cells. With the aid of Sel-green, we further demonstrated that the cytotoxicity of different selenocompounds is correlated to their ability metabolizing to selenols in cells. To the best of our knowledge, Sel-green is the first selenol probe that works under physiological conditions. The elucidation of the structure-activity relationship for selective recognition of selenols paves the way for further design of novel probes to better understand the pivotal role of Sec as well as selenoproteins in vivo

  DOI：

  10.1021/ja5099676

文献信息

• Tailored Coumarin Dyes for Photoredox Catalysis: Calculation, Synthesis, and Electronic Properties
  作者：Andrea Gualandi、Artur Nenov、Marianna Marchini、Giacomo Rodeghiero、Irene Conti、Ettore Paltanin、Matteo Balletti、Paola Ceroni、Marco Garavelli、Pier Giorgio Cozzi

  DOI：10.1002/cctc.202001690

  日期：2021.2.5

  time‐dependent density functional theory (TD‐DFT) computational modeling of coumarin dyes has been exploited for guiding the design of effective photocatalysts (PCs). A library of coumarins were investigated from the theoretical point of view and photophysical/electrochemical properties (absorption and emission spectra, E00, oxidation and reduction potentials) were evaluated. Comparison with literature values

  香豆素染料的高级时变密度泛函理论（TD-DFT）计算模型已被用来指导有效光催化剂（PC）的设计。从理论角度研究了香豆素库，并评估了光物理/电化学性质（吸收和发射光谱，E 00，氧化和还原电势）。与报告的一些候选人的文献价值进行比较已用于评估理论水平。根据获得的结果，新的还原性强的PC [ E ox（PC 。+/PC*)=−2.1 – −2.0 V vs SCE]。通过对结构-性质关系的计算研究，已经合成了许多香豆素衍生物，并在甲醛的频哪醇偶联中作为模型反应进行了评估。新型有机光氧化还原催化剂根据计算预测的数据显示了实验光物理和电化学数据，其激发态还原电势超过了高度还原的过渡金属基PC的电势。对它们作为PC的行为进行的仔细研究表明，在一般的光氧化还原催化中需要考虑到一些关键问题，从而阐明了频哪醇以及其他光氧化还原反应中这些PC的使用。
• Optischer Biosensor
  申请人：BAYER AG

  公开号：EP0429907A2

  公开（公告）日：1991-06-05

  Beschrieben wird ein neuer optischer Biosensor auf der Basis des Fluoreszenz-Energietransfers,bestehend aus a) einem festen Träger, b) einer auf a) angebrachten ein- oder mehrlagigen Langmuir-Blodgett(LB)-Schicht, c) mindestens einem Fluoreszenzfarbstoff F₁, der in mindestens einer der oberen 4 Lagen der LB-Schicht angeordnet ist, d) einem zur spezifischen Wechselwirkung befähigten Molekül (Rezeptor), das in oder an der obersten Lage der LB-Schicht gebunden oder angeordnet ist, und e) einem mobilen Fluoreszenzfarbstoff F₂, dessen Anre­gungsbande für einen Energietransfer ausreichend mit der Emissionsbande von F₁ überlappt und der e1) kovalent an einen Liganden gebunden ist, der an den Rezeptor bindungsfähig ist oder der e2) kovalent an einen anderen Rezeptor gebunden ist, der an den Komplex aus erstem Rezeptor und Ligand bindungsfähig ist, wobei der Ligand bzw. der Ligand und der zweite Rezeptor zunächst nicht an die LB-Schicht gebunden sind.

  描述了一种基于荧光能量转移的新型光学生物传感器，它由以下部分组成 a) 一个固体支架、 b) 附着在 a) 上的单层或多层朗缪尔-布洛杰特（LB）层、 c) 至少一种荧光染料 F₁，该染料至少位于 LB 层上部 4 层中的一层 d) 能够发生特异性相互作用的分子（受体），结合或排列在枸橼酸层的最上层，以及 e) 可移动的荧光染料 F₂，其激发带与 F₁ 的发射带充分重叠，以进行能量传递，并且 e1) 与能与受体结合的配体共价结合，或 e2) 与另一种能与第一受体和配体的复合物结合的受体共价结合、 其中配体或配体和第二受体最初不与枸橼酸层结合。
• Synthesis and molecular structure of 2-bromo-N-(4-(7-(diethylamino)-coumarin-3-yl)phenyl)propanamide: New coumarin-based fluorescent ATRP initiator
  作者：Ihor Kulai、Sonia Mallet-Ladeira

  DOI：10.1016/j.molstruc.2015.09.033

  日期：2016.1

  The 2-bromo-N-(4-(7-(diethylamino)-coumarin-3-yl)phenyl)propanamide was synthesized and analyzed by NMR and FT-IR spectroscopies, high resolution mass-spectrometry and single crystal X-ray diffraction. The crystal structure belongs to the monoclinic system, P2(1/c) space group with a = 14.9120(7) angstrom, b = 113177(5) angstrom, c = 12.0106(5) angstrom, alpha = 90 degrees, beta = 94.758(2)degrees, gamma = 90 degrees and V = 2020.04(16) angstrom(3). Furthermore, it was shown to be an efficient fluorescent ATRP initiator in polymerizations of acrylates. (C) 2015 Elsevier B.V. All rights reserved.
• Polymer-gebundene-Farbstoffe, Verfahren zu deren Herstellung und Verwendung
  申请人：BAYER AG

  公开号：EP0361229B1

  公开（公告）日：1994-04-27
• US5030697A
  申请人：——

  公开号：US5030697A

  公开（公告）日：1991-07-09