3-(4-nitrophenyl)-7-(N,N-diethylamino)coumarin | 82222-45-5

• 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: 3-(4-nitrophenyl)-7-(N,N-diethylamino)coumarin
• 英文别名: 7-diethylamino-3-(4-nitrophenyl)coumarin；DNC；3-(4-nitrophenyl)-7-diethylamino-coumarin；7-(Diethylamino)-3-(4-nitrophenyl)-2H-1-benzopyran-2-one；7-(diethylamino)-3-(4-nitrophenyl)chromen-2-one
• CAS: 82222-45-5
• 化学式: C₁₉H₁₈N₂O₄
• 分子量: 338.363
• InChiKey: AKVJORXFBHGDIH-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  25
• 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：
  75.4
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  3-(4-nitrophenyl)-7-(N,N-diethylamino)coumarin 在 盐酸 、 tin(II) chloride dihdyrate 、 水 、 三乙胺 作用下， 以 二氯甲烷 为溶剂， 反应 6.0h， 生成 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 、 水 作用下， 以 乙醇 为溶剂， 生成 3-(4-nitrophenyl)-7-(N,N-diethylamino)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

• Coumarin derivatives, process for their preparation, their use and
  申请人：Bayer Aktiengesellschaft

  公开号：US05300656A1

  公开（公告）日：1994-04-05

  Coumarin deviatives of the formula ##STR1## in which R.sup.1 denotes cyano, R.sup.2 represents phenyl or thiazolyl bonded in the 2-, 4-, or 5-position, R.sup.3 denotes hydrogen, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxycarbonyl-C.sub.1 -C.sub.4 -alkyl and R.sup.4 represents hydrogen, C.sub.1 -C.sub.4 -alkyl or phenylsulphonyl, where C.sub.1 -C.sub.4 -alkyl can be substituted by hydroxyl, amino, carboxyl or C.sub.1 -C.sub.4 -alkoxy-carbonyl and phenyl can be monosubstituted or disubstituted by chlorine, bromine or C.sub.1 -C.sub.4 -alkyl, where furthermore R.sup.3 and R.sup.4, together with the N atom which they substitute, can denote a morpholine ring, a piperazine ring or a triazole ring which can carry one or two substituents from the group comprising methyl, ethyl and phenyl, and where furthermore one of the radicals R.sup.2, R.sup.3 and R.sup.4 denotes or carries a primary or secondary amino group, the hydroxyl group, the carboxyl group or the C.sub.1 -C.sub.4 -alkoxy-carbonyl group or can be converted into such a group by hydrolysis or hydrogenation, are suitable for dyeing biologically active compounds.

  公式为##STR1##的香豆素衍生物，其中R.sup.1表示氰基，R.sup.2代表连接在2-、4-或5-位的苯基或噻唑基，R.sup.3表示氢、C.sub.1 -C.sub.4 -烷基或C.sub.1 -C.sub.4 -烷氧羰基-C.sub.1 -C.sub.4 -烷基，R.sup.4表示氢、C.sub.1 -C.sub.4 -烷基或苯基磺酰基，其中C.sub.1 -C.sub.4 -烷基可被羟基、氨基、羧基或C.sub.1 -C.sub.4 -烷氧羰基取代，苯基可被氯、溴或C.sub.1 -C.sub.4 -烷基单取代或双取代，此外R.sup.3和R.sup.4连同它们所取代的N原子可以表示吗啡环、哌嗪环或三唑环，该环可以携带甲基、乙基和苯基等羟基、氨基、羧基或C.sub.1 -C.sub.4 -烷氧羰基，此外，R.sup.2、R.sup.3和R.sup.4中的一个可以表示或携带一次或二次氨基、羟基、羧基或C.sub.1 -C.sub.4 -烷氧羰基，或者可以通过水解或氢化转化为这样的基团，适用于染色生物活性化合物。
• 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。
• クマリン誘導体の製造方法、発色用蛍光剤の製造方法、並びに、蛍光用色素の製造方法
  申请人：昭和化学工業株式会社

  公开号：JP2017122062A

  公开（公告）日：2017-07-13

  【課題】より簡便、且つ低コスト、高収率である３−アリール−７−Ｎ，Ｎ−ジアルキルアミノクマリン誘導体の製造方法の提供。【解決手段】４−アミノ−２−カルボキシ−フェニル基と更にフェニル基を有するアクリル酸類、及びジアルキル硫酸化合物、ルイス酸を同時又は順次継続して同浴中で反応させることによる、式（３）で表される３−アリール−７−ジアルキルアミノクマリン誘導体の製造方法。［Ａｒは置換基を有していてもよいフェニル基、チエニル基、ピリジル基、又はナフチル基；Ｒ３はＣ１〜４の直鎖／分岐鎖のアルキル基；Ｒ４はＨ、Ｃ１〜８の直鎖／分岐鎖のアルキル基、ベンジル基等］【選択図】なし

  提供一种制备3-芳基-7-二烷基氨基香豆素衍生物的方法，该方法比较简便、低成本且高收率。通过在同一反应浴中同时或顺序持续地使含有4-氨基-2-羧基苯基和进一步含有苯基的丙烯酸类化合物、二烷基硫酸化合物和路易斯酸反应，制备式（3）所示的3-芳基-7-二烷基氨基香豆素衍生物。[Ar可以是含有取代基的苯基、硫代苯基、吡啶基或萘基；R3是C1-4的直链/支链烷基；R4是H、C1-8的直链/支链烷基、苄基等]【无图】
• Coumarins: Fast Synthesis by Knoevenagel Condensation under Microwave Irradiation
  作者：Dariusz Bogdał

  DOI：10.1039/a801724g

  日期：——

  Condensation of salicyaldehyde or its derivatives with various derivatives of ethyl acetate in the presence of piperidine leads to the synthesis of coumarins by a solvent free reaction under microwave irradiation.

  在哌啶的存在下，水杨醛或其衍生物与各种乙酸乙酯衍生物的缩合导致在微波辐射下通过无溶剂反应合成香豆素。
• Substituent Effect on AIE mechanism of two coumarin derivatives: uncommon TICT fluorescence in aggregation state
  作者：Qiao Li、Yang Zhao、Zhigang Niu、Enju Wang

  DOI：10.1007/s10895-022-02933-2

  日期：2022.7

  properties and aggregation-induced emission (AIE) activities, but the AIE characteristics of them were entirely different. HNC exhibited an AIE phenomenon as the result of the restriction of twisted intramolecular charge transfer (TICT), while DNC emitted peculiar dual fluorescence which was assigned to the emission based on the inhibition of TICT state formation and the emission from the TICT state respectively

  通过水杨醛衍生物与 4-硝基苯乙腈的 Knoevenagel 缩合合成两种香豆素衍生物，7-二乙氨基-3-(4-硝基苯基)香豆素 (DNC) 和 7-羟基-3-(4-硝基苯基)香豆素 (HNC)，然后环化反应。它们都通过单晶X射线衍射进行了表征。DNC的分子通过π-π相互作用堆积，而在HNC的晶体堆积中观察到氢键相互作用而不是π-π相互作用。DNC和HNC均表现出溶剂致变色特性和聚集诱导发射(AIE)活性，但它们的AIE特性完全不同。由于扭曲的分子内电荷转移 (TICT) 的限制，HNC 表现出 AIE 现象，