2-chloro-N-(2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-7-yl)acetamide | 1308663-34-4

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉及其衍生物
• 英文名称: 2-chloro-N-(2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-7-yl)acetamide
• 英文别名: 2-chloro-N-(4-trifluoromethyl-2-oxo-1,2-dihydro-7-quinolyl)ethanamide；2-chloro-N-[2-oxo-4-(trifluoromethyl)-1H-quinolin-7-yl]acetamide
• CAS: 1308663-34-4
• 化学式: C₁₂H₈ClF₃N₂O₂
• 分子量: 304.656
• InChiKey: JLVQLAXEVWCXHZ-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.6
• 重原子数：
  20
• 可旋转键数：
  2
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.17
• 拓扑面积：
  58.2
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  2-chloro-N-(2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-7-yl)acetamide 在 potassium carbonate 、 N,N-二异丙基乙胺 作用下， 以 二氯甲烷 、 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 113.0h， 生成
  参考文献：
  名称：

  Photophysics of Coumarin and Carbostyril-Sensitized Luminescent Lanthanide Complexes: Implications for Complex Design in Multiplex Detection

  摘要：

  Luminescent lanthanide (Ln(III)) complexes with coumarin or carbostyril antennae were synthesized and their photophysical properties evaluated using steady-state and time-resolved UV-vis spectroscopy. Ligands bearing distant hydroxycoumarin-derived antennae attached through triazole linkers were modest sensitizers for Eu(III) and Tb(III), whereas ligands with 7-amidocarbostyrils directly linked to the coordination site could reach good quantum yields for multiple Ln(III), including the visible emitters Sm(III) and Dy(III), and the near-infrared emitters Nd(III) and Yb(III). The highest lanthanide-centered luminescence quantum yields were 35% (Tb), 7.9% (Eu), 0.67% (Dy), and 0.18% (Sm). Antennae providing similar luminescence intensities with 2-4 Ln-emitters were identified. Photoredox quenching of the carbostyril antenna excited states was observed for all Eu(III)-complexes and should be sensitizing in the case of Yb(III); the scope of the process extends to Ln(III) for which it has not been seen previously, specifically Dy(III) and Sm(III). The proposed process is supported by photophysical and electrochemical data. A FRET-type mechanism was identified in architectures with both distant and close antennae for all of the Lns. This mechanism seems to be the only sensitizing one at long distance and probably contributes to the sensitization at shorter distances along with the triplet pathway. The complexes were nontoxic to either bacterial or mammalian cells. Complexes of an ester-functionalized ligand were taken up by bacteria in a concentration-dependent manner. Our results suggest that the effects of FRET and photoredox quenching should be taken into consideration when designing luminescent Ln complexes. These results also establish these Ln(III)-complexes for multiplex detection beyond the available two-color systems.

  DOI：

  10.1021/jacs.6b11274
• 作为产物：
  描述：

  间苯二胺 在 三乙胺 作用下， 以 N,N-二甲基甲酰胺 为溶剂， 生成 2-chloro-N-(2-oxo-4-(trifluoromethyl)-1,2-dihydroquinolin-7-yl)acetamide
  参考文献：
  名称：

  基于线性和预组织螯合剂的明亮发光和运动惰性的镧系生物探针

  摘要：

  一系列具有三亚乙基四胺六乙酸（TTHA）和环己基三亚乙基四胺六乙酸（cyTTHA）螯合剂支架和羧甲基苯乙烯敏化剂的水溶性高发射Tb（III）和Eu（III）配合物的合成，光物理性质和动力学稳定性是报告。螯合剂的独特和模块化设计带来了惊人的水溶液发射量子产率（高达54％）以及镧系元素的光物理特性（激发态寿命长，有效斯托克斯位移大，发射峰窄） ）。此外，预组织的螯合剂（L3，L4和L6）在环境温度下在数分钟内结合金属，但在挑战溶液（EDTA，1 mM）的存在下表现出显着的抗转螯作用。此外，L4的Eu（III）配合物在HeLa细胞中可保持稳定发光，持续数小时，这表明这些化合物适用于活细胞成像应用。还制备了适用于衍生化和蛋白质生物缀合的代表性螯合剂，并用可点击的叠氮化物和炔烃部分，生物素和甲氧苄啶（TMP）进行了功能化。报道的镧系元素配合物具有出色的长波长亮度，增强的动力学惰性和适用的合成路线，是

  DOI：

  10.1021/acs.bioconjchem.6b00473

文献信息

• [EN] METAL CHELATORS FOR IMAGING, THERAPEUTICS, AND BIOANALYSIS<br/>[FR] CHÉLATEURS MÉTALLIQUES POUR L'IMAGERIE, LA THÉRAPIE, ET LA BIOANALYSE
  申请人：UNIV ILLINOIS

  公开号：WO2018048879A1

  公开（公告）日：2018-03-15

  A variety of compounds are provided capable of chelating a metal, in particular a lanthanide such as Eu(III) and Tb(III). Luminescent complexes of the compound and a metal ion are also provided, in particular luminescent metal complexes are provided containing a lanthanide such as Eu(III) or Tb(III) and a compound described herein. In some aspects, the luminescent complexes are capable of exhibiting bright emissions with high quantum yields. Methods of making the compound are provided. Methods of using the compounds and luminescent complexes are also provided, for example for imaging and therapeutic applications.

  提供了一系列化合物，能够螯合金属，特别是镧系金属如Eu(III)和Tb(III)。还提供了该化合物与金属离子形成的发光配合物，特别是提供了含有镧系金属如Eu(III)或Tb(III)和本文所述化合物的发光金属配合物。在某些方面，这些发光配合物能够展现出具有高量子产率的明亮发射。提供了制备该化合物的方法。还提供了使用这些化合物和发光配合物的方法，例如用于成像和治疗应用。
• Eu(III) Complexes as Anion-Responsive Luminescent Sensors and Paramagnetic Chemical Exchange Saturation Transfer Agents
  作者：Jacob Hammell、Leandro Buttarazzi、Ching-Hui Huang、Janet R. Morrow

  DOI：10.1021/ic200075w

  日期：2011.6.6

  innersphere with a dissociation constant of 17 μM. Luminescence emission peak changes upon addition of anion to Eu(S-THP) show that there are two distinct binding events for phosphate and methylphosphate with dissociation constants of 0.3 mM and 3.0 mM for phosphate and 0.6 mM and 9.8 mM for methyl phosphate. Eu(THPC) contains an appended carbostyril derivative as an antenna to sensitize Eu(III) luminescence

  (1 S ,4 S ,7 S ,10 S )-1,4,7,10-四(2-羟丙基)-1,4,7,10-四氮杂环十二烷( S-THP )的Eu(III)络合物被研究作为生物相关阴离子的传感器。阴离子相互作用会导致 Eu(III) 配合物的发光发射光谱、1 H NMR 光谱以及配合物的 PARACEST 光谱发生变化（PARACEST = 顺磁性化学交换饱和转移）。Eu( S-THP)的直接激发光谱和发光寿命研究) 提供有关阴离子相互作用的形态和性质的信息，包括 pH 7.2 时的碳酸盐、醋酸盐、乳酸盐、柠檬酸盐、磷酸盐和甲基磷酸盐。数据与 Eu( S-THP ) 与醋酸盐、乳酸盐和碳酸盐的内球和外球复合物的形成一致。这些阴离子的解离常数较弱，范围为 19 至 38 mM。柠檬酸盐与 Eu ( S-THP ) 的结合主要是内球体，解离常数为 17 μM。向 Eu ( S-THP )添加阴离子后的
• Electron transfer pathways in photoexcited lanthanide(<scp>iii</scp>) complexes of picolinate ligands
  作者：Daniel Kovacs、Daniel Kocsi、Jordann A. L. Wells、Salauat R. Kiraev、K. Eszter Borbas

  DOI：10.1039/d1dt00616a

  日期：——

  Eu(III), however, quantum yields were lower than in other octadentate complexes lacking pyridylcarboxylate. Complexes with more electron-poor pyridines were less emissive even when equipped with the same antenna. The oxidation and reduction potentials of the antennae and the pyridinecarboxylates, respectively, were determined by cyclic voltammetry. The obtained values were consistent with electron transfer

  合成了由1,4,7-三氮杂环壬烷骨架和三个仲酰胺连接的羧甲基苯乙烯触角组成的一系列发光镧系元素（III）配合物。金属结合位点用两个吡啶基羧酸酯供体增加，产生八齿配体。该天线在其4位上带有甲基，甲氧基甲基或三氟甲基取代基，从而具有一定范围的激发态能量和天线电子特性。Eu（III）的1 H NMR光谱）发现复合物彼此相似。通过单晶X射线晶体学在固态中获得了相似的结果，该结果表明该结构具有九个配位的金属离子，具有严重扭曲的三键三角棱镜几何形状。稳态和时间分辨发光光谱表明，触角可同时激发Tb（III）和Eu（III）），但是，量子产率低于缺少吡啶基羧酸盐的其他八齿络合物。即使配备相同的天线，具有更多电子贫乏吡啶的配合物的发射率也较低。通过循环伏安法分别测定触角和吡啶羧酸盐的氧化和还原电位。所获得的值与电子从受激天线向吡啶的转移相一致，从而提供了以前无法探索的淬灭途径，可以有效地与向镧系元素的能量转
• Metal chelators for imaging, therapeutics, and bioanalysis
  申请人：THE BOARD OF TRUSTEES OF THE UNIVERSITY OF ILLINOIS

  公开号：US10961197B2

  公开（公告）日：2021-03-30

  A variety of compounds are provided capable of chelating a metal, in particular a lanthanide such as Eu(III) and Tb(III). Luminescent complexes of the compound and a metal ion are also provided, in particular luminescent metal complexes are provided containing a lanthanide such as Eu(III) or Tb(III) and a compound described herein. In some aspects, the luminescent complexes are capable of exhibiting bright emissions with high quantum yields. Methods of making the compound are provided. Methods of using the compounds and luminescent complexes are also provided, for example for imaging and therapeutic applications.

  提供了多种能够螯合金属的化合物，特别是镧系元素，如 Eu(III)和 Tb(III)。还提供了化合物和金属离子的发光络合物，特别是含有镧系元素如 Eu(III)或 Tb(III)和本文所述化合物的发光金属络合物。在某些方面，发光络合物能够以高量子产率发出明亮的光。本文还提供了化合物的制造方法。还提供了化合物和发光复合物的使用方法，例如成像和治疗应用。