coumarin 343 acid chloride | 107408-82-2

• 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: coumarin 343 acid chloride
• 英文别名: 11-oxo-2,3,5,6,7,11-hexahydro-1H-pyrano[2,3-f]pyrido[3,2,1-ij]quinoline-10‑carbonyl chloride；acid chloride of coumarin 343；2,3,6,7-Tetrahydro-11-oxo-1H,5H,11H-[1]benzopyrano[6,7,8-ij]quinolizine-10-carbonyl chloride；4-oxo-3-oxa-13-azatetracyclo[7.7.1.02,7.013,17]heptadeca-1,5,7,9(17)-tetraene-5-carbonyl chloride
• CAS: 107408-82-2
• 化学式: C₁₆H₁₄ClNO₃
• 分子量: 303.745
• InChiKey: DDVAICQYQXLALH-UHFFFAOYSA-N

物化性质

• 沸点：
  557.8±50.0 °C(Predicted)
• 密度：
  1.46±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.5
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.38
• 拓扑面积：
  46.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  coumarin 343 acid chloride 在 三乙胺 作用下， 以 甲醇 、 二氯甲烷 为溶剂， 反应 24.0h， 生成
  参考文献：
  名称：

  有机金属化学中的荧光染料：香豆素标记的NHC-金属配合物

  摘要：

  合成了7‐NEt 2‐和ju啶亚基香豆素取代的azo盐，并分别用于制备香豆素取代的NHC金属配合物：[AuCl（NHC）]，[PdCl（烯丙基）（NHC）]，[MCl（CO） ）2（NHC）]（M = Rh，Ir），[MCl（cod）（NHC）]（M = Rh，Ir），[PdCl 2（Cl-py）（NHC）]，[PdC（烯丙基）] 2和[RuCl 2（ind）（NHC）（SIMes）] –根据相应的荧光量子产率在φ = 0.70 [Au]和φ之间进行分类= 0.005 [Ru]。配合物的荧光强度取决于金属上的电子密度，可以通过吸电子基团增加，通过供电子基团减少。在这种情况下，[MCl（cod）（NHC）]（M = Rh，Ir）中的两个CO取代鳕鱼（1,5-环辛二烯）生成[MCl（CO）2（NHC）]，最高荧光增加18倍。[MCl（cod）（NHC）]或浸透的滤纸条溶液用CO处理，并用360

  DOI：

  10.1002/ejic.201800395
• 作为产物：
  描述：

  香豆素343甲酯 在 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 24.5h， 生成 coumarin 343 acid chloride
  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

• SMMR (small molecule metabolite reporters) for use as in vivo glucose biosensors
  申请人：Bellott M. Emile

  公开号：US20070110672A1

  公开（公告）日：2007-05-17

  Small Molecule Metabolite Reporters (SMMRs) for use as in vivo glucose biosensors, sensor compositions, and methods of use, are described. The SMMRs include boronic acid-containing xanthene, coumarin, carbostyril and phenalene-based small molecules which are used for monitoring glucose in vivo, advantageously on the skin.

  用于体内葡萄糖生物传感器的Small Molecule Metabolite Reporters (SMMRs)、传感器组合物及其使用方法被描述。SMMRs包括含有硼酸的小分子，基于黄烷、香豆素、卡波罗司坦和菲内烯，用于监测体内的葡萄糖，优选在皮肤上。
• New Ruthenium(II) Complexes Functionalized with Coumarin Derivatives: Synthesis, Energy-Transfer-Based Sensing of Esterase, Cytotoxicity, and Imaging Studies
  作者：Mei-Jin Li、Keith Man-Chung Wong、Changqing Yi、Vivian Wing-Wah Yam

  DOI：10.1002/chem.201103025

  日期：2012.7.9

  Two new bichromophoric ruthenium(II) complexes, [Ru(bpy)2(bpy‐CM)](PF6)2 and [Ru(bpy)2(bpy‐CM343)](PF6)2 (bpy=2,2′‐bipyridine, CM=coumarin) with appended coumarin ligands have been designed and synthesized. The energy‐transfer‐based sensing of esterase by the complexes has been studied by using UV/Vis and luminescence spectroscopic methods. The cytotoxicity and the cellular uptake of one of the complexes

  两个新的双发色钌（II）络合物[Ru（bpy）2（bpy-CM）]（PF 6）2和[Ru（bpy）2（bpy‐CM343）]（PF 6）2（bpy = 2,2已设计并合成了带有附加香豆素配体的``-bipyridine，CM =香豆素）。通过使用UV / Vis和发光光谱法研究了配合物基于能量转移的酯酶传感。还研究了一种复合物的细胞毒性和细胞摄取。
• A calixarene-based fluorescent ratiometric temperature probe
  作者：Brunella Bardi、Irene Tosi、Federica Faroldi、Laura Baldini、Francesco Sansone、Cristina Sissa、Francesca Terenziani

  DOI：10.1039/c9cc04577e

  日期：——

  We report the first macrocycle-based ratiometric molecular thermometer exploiting the conformational thermosensitivity of a calixarene functionalized with two different fluorophores. Thanks to the dependence on temperature of the efficiency of excitation energy transfer between the organic fluorophores, the thermometer works over a 60 °C-wide temperature range with a sensitivity of 4% °C−1.

  我们报告了第一个基于大环的比例式分子温度计，利用了用两个不同的荧光团官能化的杯芳烃的构象热敏性。由于温度依赖于有机荧光团之间的激发能传递效率，因此温度计可在60°C宽的温度范围内工作，灵敏度为4％C -1。
• Evaluation of coumarin-tagged deferoxamine as a Zr(IV)-based PET/fluorescence dual imaging probe
  作者：Giammarco Maria Romano、Virginia Zizi、Giulia Salvatore、Riccardo Bani、Monica Mangoni、Silvia Nistri、Giulia Anichini、Yschtar Tecla Simonini Steiner、Daniele Bani、Antonio Bianchi、Andrea Bencini、Matteo Savastano

  DOI：10.1016/j.jinorgbio.2023.112259

  日期：2023.8

  performed on X-irradiated MDA-MB 231 cells showed no interference of ZrDFOC with radiosensitivity. Morphological biodistribution (confocal fluorescence, transmission electron microscopy) assays on the same cells suggested internalization of the complex through endocytosis. Overall, these results support fluorophore-tagged DFO as a suitable option to achieve dual imaging (PET/fluorescence) probes based on

  去铁胺 (DFO) 目前是89 Zr 4+的黄金标准螯合剂，89 Zr 4+ 是一种有前景的正电子发射断层扫描成像 (PET) 核素。天然铁载体 DFO 先前已与荧光团结合以获得 Fe(III) 传感分子。在本研究中，制备了 DFO 的荧光香豆素衍生物 (DFOC) 并对其进行了表征（电位分析、紫外-可见光谱），了解其质子化和对 PET 相关离子（Cu(II)、Zr(IV)）的金属配位特性。 ），证明与原始 DFO 具有很强的相似性。金属结合后 DFOC 荧光发射的保留已被检查（荧光分光光度法），因为它会并且确实允许光学（荧光）成像，从而解锁89 Zr(IV) 示踪剂的双峰（PET/荧光）成像。对 NIH-3 T3 成纤维细胞和 MDA-MB 231 乳腺癌细胞系的结晶紫和 MTT 测定分别证明，在常用放射诊断浓度的 ZrDFOC 下，没有细胞毒性或代谢损伤。对 X 射线照射的 MDA-MB
• Detection and Mechanistic Studies of Multicomponent Assembly by Fluorescence Resonance Energy Transfer
  作者：Ronald K. Castellano、Stephen L. Craig、Colin Nuckolls、Julius Rebek

  DOI：10.1021/ja994397m

  日期：2000.8.23

  The kinetics and thermodynamics of multicomponent assembly in organic solution are investigated using fluorescence resonance energy transfer (FRET). Calix[4]arenes functionalized with ureas on their wider rims dimerize in organic solution, via intermolecular hydrogen bonding, to form encapsulation complexes. When one calixarene component is outfitted with a donor fluorophore and the other with an acceptor, dimerization brings the chromophores within 20 Angstrom, a distance suitable for efficient energy transfer to occur between them. Excitation of the donor results in two colors of emitted light: one fluorescence band at the donor emission wavelength, and a second at the acceptor emission wavelength signaling the noncovalent union of three species-donor, acceptor, and small-molecule guest. By monitoring these wavelengths, assembly and dissociation processes are observed in real time at nanomolar concentrations. Rate and association constants for assembly processes are determined for the first time, and they reveal unexpected contributions from the structure and concentration of the monomer. Finally, the combination of FRET and the molecular recognition capabilities of the encapsulation complexes provides a sensitive and specific method for small-molecule sensing.