51473-74-6Relevant academic research and scientific papers
A new water-soluble two-photon fluorescent probe for detection of trace benzoyl peroxide in wheat flour and in living cell and tissue imaging
Ding, Haiyuan,Yuan, Gangqiang,Zhou, Liyi
, p. 3169 - 3173 (2019)
Benzoyl peroxide (BPO), a member of small-molecule reactive oxygen species (ROS), has attracted considerable attention because of its impact on human health and industrial importance. Herein, to quantitatively detect BPO in real samples and for fluorescen
Solid-state fluorescence properties of small iminocoumarin derivatives and their analogues in the coumarin series
Abid-Jarraya, Nihel,Khemakhem, Kacem,Turki-Guermazi, Hamida,Abid, Souhir,Saffon, Nathalie,Fery-Forgues, Suzanne
, p. 177 - 184 (2016)
Considering the many potential applications of fluorescent materials, dyes that exhibit emission in the solid state are in high demand, especially if they are easy to prepare and inexpensive. In this respect, exploring the behaviour of basic iminocoumarins seemed relevant. The spectroscopic properties of 3-cyano-7-diethylamino-2-iminocoumarin and a derivative bearing an ethoxycarbonyl group were therefore studied in the solid state, and a comparison was made with the corresponding coumarin. The three compounds had very close fluorescence properties in solution. In contrast, the coumarin derivative was much more emissive in the solid state than the iminocoumarins. This discrepancy was tentatively related to the crystal packing modes. A comparison was made with 7-diethylaminocoumarin to clarify the role of the cyano group, which may not be advantageous from a spectroscopic viewpoint. Using a solvent-exchange method, the three cyano compounds generated elongated microparticles, the substituted iminocoumarin derivative even led to flat microfibers. This work shows that small coumarins are valuable solid-state fluorescent dyes while small iminocoumarins should be used as building blocks to access more elaborated compounds if solid-state applications are envisaged.
A Minimalistic Coumarin Turn-On Probe for Selective Recognition of Parallel G-Quadruplex DNA Structures
Deiana, Marco,Obi, Ikenna,Andreasson, M?ns,Tamilselvi, Shanmugam,Chand, Karam,Chorell, Erik,Sabouri, Nasim
, p. 1365 - 1376 (2021/08/25)
G-quadruplex (G4) DNA structures are widespread in the human genome and are implicated in biologically important processes such as telomere maintenance, gene regulation, and DNA replication. Guanine-rich sequences with potential to form G4 structures are prevalent in the promoter regions of oncogenes, and G4 sites are now considered as attractive targets for anticancer therapies. However, there are very few reports of small "druglike"optical G4 reporters that are easily accessible through one-step synthesis and that are capable of discriminating between different G4 topologies. Here, we present a small water-soluble light-up fluorescent probe that features a minimalistic amidinocoumarin-based molecular scaffold that selectively targets parallel G4 structures over antiparallel and non-G4 structures. We showed that this biocompatible ligand is able to selectively stabilize the G4 template resulting in slower DNA synthesis. By tracking individual DNA molecules, we demonstrated that the G4-stabilizing ligand perturbs DNA replication in cancer cells, resulting in decreased cell viability. Moreover, the fast-cellular entry of the probe enabled detection of nucleolar G4 structures in living cells. Finally, insights gained from the structure-activity relationships of the probe suggest the basis for the recognition of parallel G4s, opening up new avenues for the design of new biocompatible G4-specific small molecules for G4-driven theranostic applications.
A coumarin based fluorescent chemodosimeter for phosgene gas detection instantaneously in solution and the gas phase
Paul, Sima,Ghosh, Pritam,Roy, Partha
, p. 5784 - 5791 (2020/04/27)
A coumarin based compound, 7-(diethylamino)-2-oxo-2H-chromene-3-carbaldehyde oxime (DCCO), has been developed as a visual fluorescent chemodosimeter for selective detection of highly toxic phosgene gas. DCCO exhibits absorption bands at 330 nm and 425 nm. In the presence of phosgene, the absorbance at 330 nm increases and the peak at 425 nm is shifted to 420 nm with decreasing absorbance accompanying a color change from yellow to colorless. The fluorescence intensity of the probe at 483 nm is enhanced in the presence of phosgene (λex = 425 nm) but nerve agents and other acid chlorides including trisphosgene could not induce any significant enhancement of the fluorescence. DCCO on interaction with phosgene is converted to the corresponding nitrile derivative, 7-(diethylamino)-2-oxo-2H-chromene-3-carbonitrile (DCC). The quantum yield has been increased 13 fold on conversion from DCCO to DCC. The fluorescence enhancement has been explained by the ICT mechanism, which has been supported by theoretical calculations. It exhibits a rapid response for naked eye detection of phosgene. DCCO has been used for the detection of phosgene in solution and the gas phase.
Reinvestigation of the synthesis of “covalent-assembly” type probes for fluoride ion detection. Identification of novel 7-(diethylamino)coumarins with aggregation-induced emission properties
Quesneau, Valentin,Roubinet, Beno?t,Renard, Pierre-Yves,Romieu, Anthony
, (2019/11/05)
An unprecedented C-3 functionalization of 4-(diethylamino)salicylaldehyde through a Friedel-Crafts type alkylation reaction has been discovered during the synthesis of “covalent-assembly”-based fluorescent probes for detection of fluoride ions. The resulting Friedel-Crafts adduct was successfully used for the preparation of two novel 8-substituted 7-(diethylamino)coumarin dyes. The photophysical study of these fluorophores has enabled us to highlight their remarkable aggregation-induced emission (AIE) properties characterized by a yellow-orange emission of aggregates in water. Therefore, 4-(tert-butyldimethylsilyloxy)benzyl substituent was identified as a novel AIE-active moiety which could be seen as a possible alternative to popular tetraphenylethylene (TPE).
ZIF-8 nanoparticles as an efficient and reusable catalyst for the Knoevenagel synthesis of cyanoacrylates and 3-cyanocoumarins
Kolmykov, Oleksii,Chebbat, Nassima,Commenge, Jean-Marc,Medjahdi, Ghouti,Schneider, Rapha?l
, p. 5885 - 5888 (2016/12/14)
Zeolitic imidazolate framework (ZIF-8) particles with an average size of ca. 355 nm and a specific surface area of 1786 m2.g?1were used as an heterogenous catalyst for the Knoevenagel synthesis of α,β-unsaturated cyanoesters and 3-cy
A cost-effective and green aqueous synthesis of 3-substituted coumarins catalyzed by potassium phthalimide
Kiyani, Hamzeh,Daroonkala, Masoumeh Darzi
, p. 449 - 456 (2015/10/19)
An efficient procedure for the synthesis of various 2-imino-2H-chromene-3-carbonitriles, 2-oxo- 2H-chromene-3-carbonitriles as well as 2-oxo-2H-chromene-3-carboxylic acids is reported. It has been found that potassium phthalimide (PPI) catalyse the Knoevenagel condensation reaction of salicylaldehydes and activated β- dicarbonyl compounds efficiently under aqueous conditions at room temperature. This approach provides many merits such as high yields of products, clean, simple work-up, waste free, mild reaction conditions, commercially available organocatalyst, and the use of water as environmentally benign solvent.
New green, recyclable magnetic nanoparticles supported amino acids as simple heterogeneous catalysts for knoevenagel condensation
Girija,Naik, H.S. Bhojya,Kumar, B. Vinay,Sudhamani,Harish
, p. 468 - 477 (2013/08/23)
Coumarin derivatives were synthesized using magnetically recoverable iron oxide nanoparticles supported amino acids as heterogeneous catalysts via one-pot multi component reaction using MW irradiation. Easy recovery of the catalyst using an external magne
A highly specific tetrazole-based chemosensor for fluoride ion: A new sensing functional group based on intramolecular proton transfer
Li, Ju-Ying,Zhou, Xin-Qi,Zhou, Yi,Fang, Yuan,Yao, Cheng
supporting information, p. 66 - 70 (2013/02/23)
A simple but highly selective colorimetric and fluorescent chemosensor for fluoride ion has been prepared based on coumarin chromophore and 1H-tetrazole. Tetrazole functional group provided a novel sensing functional group containing the ESIPT structure f
An efficient one-pot synthesis of coumarins mediated by propylphosphonic anhydride (T3P) via the Perkin condensation
Augustine, John Kallikat,Bombrun, Agnes,Ramappa, Balakrishna,Boodappa, Chandrakantha
experimental part, p. 4422 - 4425 (2012/09/25)
An efficient one-pot synthesis of coumarins mediated by T3P, a mild and low toxic peptide coupling agent, via the Perkin condensation has been demonstrated.
