2-氯-N-(4-甲基-2-氧代-1,2-二氢-7-喹啉基)乙酰胺 | 183613-11-8

• 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
• 中文名称: 2-氯-N-(4-甲基-2-氧代-1,2-二氢-7-喹啉基)乙酰胺
• 英文名称: 2-chloro-N-(4-methyl-2-oxo-1,2-dihydroquinolin-7-yl)acetamide
• 英文别名: Carbostyril 124 N-Carboxymethyl Chloride；2-chloro-N-(4-methyl-2-oxo-1H-quinolin-7-yl)acetamide
• CAS: 183613-11-8
• 化学式: C₁₂H₁₁ClN₂O₂
• 分子量: 250.685
• InChiKey: USRUAYVEQRYSTQ-UHFFFAOYSA-N

物化性质

• 沸点：
  519.3±50.0 °C(Predicted)
• 密度：
  1.358±0.06 g/cm3(Predicted)
• 溶解度：
  二甲基甲酰胺

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  17
• 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：
  2

反应信息

• 作为反应物：
  描述：

  2-氯-N-(4-甲基-2-氧代-1,2-二氢-7-喹啉基)乙酰胺 在 N,N-二异丙基乙胺 作用下， 以 氯仿 、 N,N-二甲基甲酰胺 为溶剂， 反应 12.0h， 生成 2-[4,10-bis(2-amino-2-oxoethyl)-7-[2-[(4-methyl-2-oxo-1H-quinolin-7-yl)amino]-2-oxoethyl]-1,4,7,10-tetrazacyclododec-1-yl]acetamide
  参考文献：
  名称：

  Cocktails of Tb³⁺ and Eu³⁺ Complexes:  A General Platform for the Design of Ratiometric Optical Probes

  摘要：

  Fluorescent and luminescent reporters that signal molecular events of interest by modulating the ratio of peaks in their emission profile have advantages over reporters that simply modulate their emission intensity, since ratiometric measurement is concentration-independent and allows them to be effective in complex contexts, such as living cells or sensor microarrays. We herein describe a general platform for the design of ratiometric probes based on a heterometallic Tb3+/Eu3+ bis-lanthanide ensemble, consisting of a mixture, or "cocktail", of otherwise identical heterometalated chelates. The chelate contains an organic photon antenna that sensitizes the Tb3+/Eu3+ luminescence. The contributions of the two metals to the composite luminescence spectrum can be tuned to the same relative scale by adjusting the stoichiometry of the cocktail, allowing subtle changes in their ratio to be accurately measured. Importantly, the ratio responds to chemical and environmental changes experienced by the photon antenna, making the system an ideal platform for the design of chemical and enzymatic probes. As proofs of concept, we describe a ratiometric probe for esterase activity and a polarity-responsive ratiometric sensor.

  DOI：

  10.1021/ja070867y
• 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-氯-N-(4-甲基-2-氧代-1,2-二氢-7-喹啉基)乙酰胺
  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。
• 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
• Co(II) Macrocyclic Complexes Appended with Fluorophores as paraCEST and cellCEST Agents
  作者：Akanksha Patel、Samira M. Abozeid、Paul J. Cullen、Janet R. Morrow

  DOI：10.1021/acs.inorgchem.0c02470

  日期：2020.11.16

  Four high-spin macrocyclic Co(II) complexes with hydroxypropyl or amide pendants and appended coumarin or carbostyril fluorophores were prepared as CEST (chemical exchange saturation transfer) MRI probes. The complexes were studied in solution as paramagnetic CEST (paraCEST) agents and after loading into Saccharomyces cerevisiae yeast cells as cell-based CEST (cellCEST) agents. The fluorophores attached

  制备了四个带有羟丙基或酰胺侧基的高自旋大环Co（II）配合物，并附加了香豆素或卡苯乙烯基荧光团作为CEST（化学交换饱和转移）MRI探针。在溶液中以顺磁性CEST（paraCEST）剂以及装入酿酒酵母后对复合物进行了研究酵母细胞作为基于细胞的CEST（cellCEST）试剂。通过酰胺键连接到配合物上的荧光团通过电离归因于酰胺NH连接基团的基团，使所有四个配合物的paraCEST特性具有不同寻常的pH依赖性。当pH从5增加到7.5时，羟丙基基络合物的最远CEST峰变化了〜90 ppm。在酸性pH值下，Co（II）配合物表现出三到四个CEST峰，并且在200 ppm处位移最大的CEST峰。该配合物表现出明显的顺磁性水质子转移，这是开发cellCEST试剂所必需的。质子共振的大位移归因于中性pH下的内层水，如温度变化17所示NMR光谱学研究。用这些paraCEST试剂之一标记酵母，通过荧光显微镜
• 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。
• Photophysics of Coumarin and Carbostyril-Sensitized Luminescent Lanthanide Complexes: Implications for Complex Design in Multiplex Detection
  作者：Daniel Kovacs、Xi Lu、Lívia S. Mészáros、Marjam Ott、Julien Andres、K. Eszter Borbas

  DOI：10.1021/jacs.6b11274

  日期：2017.4.26

  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.