6093-71-6Relevant academic research and scientific papers
Hafnium chloride tetrahydrofuran complex-catalyzed Diels-Alder cycloadditions of 3-ethoxycarbonylcoumarins with 1,3-dienes under solvent-free conditions
Fringuelli, Francesco,Girotti, Rugiada,Pizzo, Ferdinando,Zunino, Ennio,Vaccaro, Luigi
, p. 297 - 300 (2006)
Hafnium chloride tetrahydrofuran complex (HfCl4·2 THF) is an efficient catalyst for the Diels-Alder cycloadditions of 3-ethoxycarbonylcoumarins 1a-c and 1,3-butadienes 2x-z under solvent-free conditions furnishing the corresponding cycloadducts in excellent yields. This salt is an air stable Lewis acid and therefore the reactions can be performed in air atmosphere making the procedure simple to be carried out.
Design, synthesis and anti-Alzheimer's activity of novel 1,2,3-triazole-chromenone carboxamide derivatives
Rastegari, Arezoo,Nadri, Hamid,Mahdavi, Mohammad,Moradi, Alireza,Mirfazli, Seyedeh Sara,Edraki, Najmeh,Moghadam, Farshad Homayouni,Larijani, Bagher,Akbarzadeh, Tahmineh,Saeedi, Mina
, p. 391 - 401 (2019)
Alzheimer's disease (AD) is a well-known neurodegenerative disorder affecting millions of old people worldwide and the corresponding epidemiological data highlights the significance of the disease. As AD is a multifactorial illness, various single-target directed drugs that have reached clinical trials have failed. Therefore, various factors associated with outset of AD have been considered in targeted drug discovery and development. In this work, a wide range of 1,2,3-triazole-chromenone carboxamides were designed, synthesized, and evaluated for their cholinesterase inhibitory activity. Among them, N-(1-benzylpiperidin-4-yl)-7-((1-(3,4-dimethylbenzyl)-1H-1,2,3-triazol-4-yl)methoxy)-2-oxo-2H-chromene-3-carboxamide (11b) showed the best acetylcholinesterase inhibitory activity (IC50 = 1.80 μM), however, it was inactive toward butyrylcholinesterase. It should be noted that compound 11b was evaluated for its BACE1 inhibitory activity and calculated IC50 = 21.13 μM confirmed desired inhibitory activity. Also, this compound revealed satisfactory neuroprotective effect against H2O2-induced cell death in PC12 neurons at 50 μM as well as metal chelating ability toward Fe2+, Cu2+, and Zn2+ ions.
Synthesis and structural characterization of some divalent metal complexes: DNA binding and antitumor activity
El-Bindary, Ashraf El Bindary,Hassan,El-Afify
, p. 213 - 228 (2017)
New Complexes (1–4) of Cu(II), Ni(II) Zn(II) and Mn(II) with 3-Ethoxy-6-(phenyl azo)-7-hydroxy coumarin (HL) have been prepared and characterized by elemental analyses, IR, 1H NMR, 13C NMR, mass spectroscopy and UV–Visible spectra as well as thermal measurements. IR spectra showed that the ligand (HL) acts as a monobasic bidentate and coordinating via the nitrogen atom of the azo group ([sbnd]N[dbnd]N[sbnd]) and oxygen atom of the deprotonated phenolic OH group. The molar conductance measurements proved that all the complexes are non-electrolytes. Also the important fragments in the ligand and Ni(II) complex were done using mass spectra and the main peaks were corresponding to the molecular weights. The molecular and electronic structures of the investigated compounds were also studied using quantum chemical calculations. The bonding parameters of the complexes have been calculated. Molecular docking was used to predict the binding between azo compound with the receptor of 3hb5-oxidoreductase receptor of breast cancer and of 2q7k-hormone of prostate cancer. The calf thymus DNA binding activity of the ligand and its metal complexes was studied by absorption spectra and viscosity measurement. The antitumor activity of the ligand and its metal complexes was tested against human cancer MCV-7 (breast cancer).
Coumarin-derived Fe3+-selective fluorescent turn-off chemosensors: Synthesis, properties, and applications in living cells
En, Da,Guo, Yuan,Chen, Bo-Ting,Dong, Biao,Peng, Meng-Jiao
, p. 248 - 253 (2014)
A novel coumarin-based fluorogenic probe bearing the tris unit (DAT-1) with high selectivity and suitable affinity toward Fe3+ over other cations tested was developed in biological systems. The sensing mechanism was studied by quantum calculations. The probe can be applied to the monitoring of Fe3+ in aqueous solution with a pH span of 3-8. In addition, biological imaging, membrane permeability and nontoxicity demonstrate that DAT-1 could act as a turn-off fluorescent chemosensor for Fe3+ in living cells.
7-Alkoxy-appended coumarin derivatives: synthesis, photo-physical properties, aggregation behaviours and current-voltage (I-V) characteristic studies on thin films
Rudra Paul, Abhijit,Dey, Bapi,Suklabaidya, Sudip,Hussain, Syed Arshad,Majumdar, Swapan
, p. 10212 - 10223 (2021)
In this study, we designed and synthesised a series of coumarin derivatives appended with a long alkoxy chain on the seventh position of the coumarin-3-carboxylate/carboxylic acid core to make thin film materials. Synthesised compounds were characterized by their UV and fluorescence spectra in solutions as well as their films prepared by both LB and spin-coated methods. The surface morphology and electrical behaviour of thin films were judged by AFM, SEM andI-Vcharacteristic mapping respectively. Isotherm, UV-Vis absorption and fluorescence spectroscopic investigations revealed the formation of aggregates on thin films. The result of SEM and AFM images provides the information about the length and height of aggregates on the thin films of coumarin derivatives. FromI-Vcharacteristics, it was found that at room temperature, the spin-coated films of coumarin derivatives containing an ester functional group exhibited a threshold switching behaviour, whereas derivatives containing the carboxylic acid functional group showed both threshold and bipolar switching behaviours. We also noticed that theI-Vcharacteristic features of synthesized materials depended on the length of the alkyl chain of individual series.
A sustainable innovation for the tandem synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL im from: Thermomyces lanuginosus in continuous-flow microreactors
Chen, Ping-Feng,Du, Li-Hua,Long, Rui-Jie,Luo, Xi-Ping,Xue, Miao
, p. 13252 - 13259 (2020)
We developed an efficient and environmentally friendly two-step tandem methodology for the synthesis of sugar-containing coumarin derivatives catalyzed by lipozyme TL IM from Thermomyces lanuginosus in continuous-flow microreactors. Compared to those observed for other methods, the salient features of this work including green reaction conditions, short residence time (50 min), and catalysts are more readily available and the biocatalysis reaction process is efficient and easy to control. This two-step tandem synthesis of coumarin derivatives using the continuous-flow technology is a proof of concept that opens the use of enzymatic microreactors in coumarin derivative biotransformations.
Selective and "turn-off" fluorimetric detection of mercury(II) based on coumarinyldithiolane and coumarinyldithiane in aqueous solution
Guo, Yuan,An, Jing,Tang, Haoyang,Peng, Mengjiao,Suzenet, Franck
, p. 155 - 163 (2015)
In this work, five novel coumarin-based fluorescent probes for mercury ions were developed. The recognition of mercury ions was performed via the mercury(II)-promoted desulfurization of the probes and a reasonable reaction mechanism was proposed and verified by thin layer chromatography (TLC), 1H nuclear magnetic resonance (1H NMR) and fluorescence intensity measurements. All the probes showed excellent optical properties and exclusively distinguish mercury ions from various metal ions in aqueous solutions at pH 7.4. The linear response of the fluorescence emission intensity for all the probes to the concentration of mercury ions was obtained over a wide range of 0.06-1.5 μM (0.06-0.9 μM for probe 3e). In addition, the biological toxicity and the confocal fluorescence images of probe 3a were also tested on MCF-7 cells.
Ratiometric assay of CARM1 activity using a FRET-based fluorescent probe
Ohta, Yuhei,Wakita, Hiroo,Kawaguchi, Mitsuyasu,Ieda, Naoya,Osada, Shigehiro,Nakagawa, Hidehiko
, (2019)
One of the regulatory mechanisms of epigenetic gene expression is the post-translational methylation of arginine residues, which is catalyzed by protein arginine methyltransferases (PRMTs). Abnormal expression of PRMT4/CARM1, one of the PRMTs, is associated with various diseases, including cancers. Here, we designed and synthesized a F?rster resonance energy transfer (FRET)-based probe, FRC, which contains coumarin and fluorescein fluorophores at the N-terminus and C-terminus of a peptide containing an arginine residue within an appropriate amino acid sequence to serve as a substrate of CARM1; the two fluorophores act as a FRET donor and a FRET acceptor, respectively. Since trypsin specifically hydrolyzes the arginine residue, but not a monomethylarginine or dimethylarginine residue, CARM1 activity can be evaluated from the change of the coumarin/fluorescein fluorescence ratio of FRC in the presence of trypsin.
Discovery of quinazoline-based fluorescent probes to α1-adrenergic receptors
Zhang, Wei,Ma, Zhao,Li, Wenhua,Li, Geng,Chen, Laizhong,Liu, Zhenzhen,Du, Lupei,Li, Minyong
, p. 502 - 506 (2015)
α1-Adrenergic receptors (α1-ARs), as the essential members of G protein-coupled receptors (GPCRs), can mediate numerous physiological responses in the sympathetic nervous system. In the current research, a series of quinazoline-based small-molecule fluorescent probes to α1-ARs (1a-1e), including two parts, a pharmacophore for α1-AR recognition and a fluorophore for visualization, were well designed and synthesized. The biological evaluation results displayed that these probes held reasonable fluorescent properties, high affinity, accepted cell toxicity, and excellent subcellular localization imaging potential for α1-ARs.
A coumarin-based fluorescent probe for the fast detection of Pd0 with low detection limit
Liu, Yunchang,Xiang, Kaiqiang,Guo, Min,Tian, Baozhu,Zhang, Jinlong
, p. 1451 - 1455 (2016)
A off-on coumarin-based fluorescent probe for the fast detection of Pd0 is designed and synthesized. The probe shows not only good selectivity but also fast response to Pd0 in phosphate buffered saline (PBS) solution. The absorption band at 412 nm rises sharply as well as the fluorescence at 450 nm after the addition of Pd0 within few minutes. The detection limit is as low as 0.34 nM. The probe shows nonfluorescence when it conjuncted with allyl carbonate ester which destroys the Intramolecular Charge Transfer (ICT) system. The effect of Pd0 to the probe can change the structure and make the departure of the conjuncted allyl carbonate ester. As a result, the fluorogen is exposed and it shows fluorescence.
