10242-13-4Relevant articles and documents
Novel intramolecular charge transfer effect-based ligands and aggregation-induced emission-active europium complexes: synthesis, characterization, and fluorescence properties
Yang, Shuaishuai,Guo, Zuping,Hu, Zhongqian,Guo, Dongcai
, p. 306 - 315 (2021)
Two novel coumarin derivatives and the corresponding europium complexes were prepared using a simple procedure. The pH response of the ligand and the aggregation-induced emission (AIE) properties of the target europium complex were studied. The ligand had an intramolecular charge transfer (ICT) effect and was linearly and sharply responsive under acidic conditions. The goal europium complexes exhibited excellent AIE performance when subjected to increasing concentrations of target europium complex or proportion of poor solvent. The effect of substituents on fluorescence strength or thermogravimetric and electrochemical properties was further investigated. The target complexes displayed the typical fluorescence of europium. The fluorescence amplitude of the target europium complexes was enhanced by the addition of electron-donating groups to ligands. Thermogravimetric research findings indicated that the target complexes possessed extreme thermal stability. Electrochemistry discovery findings indicated that the highest occupied molecular orbit energy level of EuL1 was greater than EuL2, but the lowest unoccupied molecular orbit energy level was smaller than that of EuL2. These complexes could be applied in medicinal chemistry, substance chemistry, and fluorescence labelling areas.
Et3N catalyzed cascade reaction of Meldrum’s acid with ortho-hydroxyaryl aldehydes for the synthesis of coumarin-3-carboxylic acids under solvent-less condition
Pan, Wan-Yü,Xiao, Yü-Meng,Xiong, Hou-Qing,Lü, Cheng-Wei
, p. 7057 - 7063 (2016)
Abstract: The synthesis of coumarin-3-carboxylic acids in good yields is realized through a triethylamine catalyzed Knoevenagel-intramolecular cyclization tandem reaction of Meldrum’s acid with various ortho-hydroxyaryl aldehydes. This method expands the catalyst library about the synthesis of coumarin-3-carboxylic acids and also has advantages of using much less water as solvent, a cheap and eco-friendly catalyst, clean reaction conditions, simple workup procedure and easy isolation. Graphical Abstract: [Figure not available: see fulltext.]
Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity
Liu, Hao,Ren, Zi-Li,Wang, Wei,Gong, Jie-Xiu,Chu, Ming-Jie,Ma, Quan-Wei,Wang, Jie-Chun,Lv, Xian-Hai
, p. 81 - 87 (2018)
The identification of novel Topoisomerase II (Topo II) inhibitors is one of the most attractive directions in the field of bactericide research and development. In our ongoing efforts to pursue the class of inhibitors, six series of 70 novel coumarin-pyrazole carboxamide derivatives were designed and synthesized. As a result of the evaluation against four destructive bacteria, including Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8III-k (MIC = 0.25 mg/L) showed considerable inhibitory activity than ciprofloxacin (MIC = 0.5 mg/L) against Escherichia coli and 8V-c (MIC = 0.05 mg/L) exhibited excellent antibacterial activity than ciprofloxacin (MIC = 0.25 mg/L) against Salmonella. The selected compounds (8III-k, 8V-c and 8V-k) exhibit potent inhibition against Topo II and Topo IV with IC50 values (9.4–25 mg/L). Molecular docking model showed that the compounds 8V-c and 8V-k can bind well to the target by interacting with amino acid residues. It will provide some valuable information for the commercial Topo II inhibiting bactericides.
Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach
Martínez, Joel,Sánchez, Lilibeth,Pérez, F. Javier,Carranza, Vladimir,Delgado, Francisco,Reyes, Leonor,Miranda, René
, (2016)
A green contribution in short reaction times with moderate yields to produce coumarin-3-carboxylic acids is offered. Five different modes to activate the reactions (microwave, near-infrared, mechanical milling, and ultrasound) were compared with mantle heating in the presence or absence of ethanol, a green solvent. Near-infrared and microwave irradiations deliver the best yields in contrast to ultrasound and mechanical milling; moreover, these four processes offered shorter reaction times in comparison with the conventional mantle heating method. It is also important to highlight that the obtained molecules were produced without the requirement of a catalyst and two nonconventional energies forms are presented as new processes.
Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. Pylori strains and ags cell proliferation
Sisto, Francesca,Carradori, Simone,Guglielmi, Paolo,Traversi, Carmen Beatrice,Spano, Mattia,Sobolev, Anatoly P.,Secci, Daniela,Di Marcantonio, Maria Carmela,Haloci, Entela,Grande, Rossella,Mincione, Gabriella
, p. 1 - 21 (2020)
This study reports on the synthesis, structural assessment, microbiological screening against several strains of H. pylori and antiproliferative activity against human gastric adenocarcinoma (AGS) cells of a large series of carvacrol-based compounds. Structural analyses consisted of elemental analysis,1 H/13 C/19 F NMR spectra and crystallographic studies. The structure-activity relationships evidenced that among ether derivatives the substitution with specific electron-withdrawing groups (CF3 and NO2) especially in the para position of the benzyl ring led to an improvement of the antimicrobial activity, whereas electron-donating groups on the benzyl ring and ethereal alkyl chains were not tolerated with respect to the parent compound (MIC/MBC = 64/64 μg/mL). Ester derivatives (coumarin-carvacrol hybrids) displayed a slight enhancement of the inhibitory activity up to MIC values of 8–16 μg/mL. The most interesting compounds exhibiting the lowest MIC/MBC activity against H. pylori (among others, compounds 16 and 39 endowed with MIC/MBC values ranging between 2/2 to 32/32 μg/mL against all the evaluated strains) were also assayed for their ability to reduce AGS cell growth with respect to 5-Fluorouracil. Some derivatives can be regarded as new lead compounds able to reduce H. pylori growth and to counteract the proliferation of AGS cells, both contributing to the occurrence of gastric cancer.
NOVEL REACTIONS OF CARBON SUBOXIDE. IV. SYNTHESIS OF SOME N-HYDROXY-2-OXO-2H-1-BENZOPYRAN-3-CARBOXAMIDES
Bonsignore, Leonardo,Loy, Guiseppe,Secci, Mario
, p. 5013 - 5016 (1983)
Some N-hydroxy-2-oxo-2H-1-benzopyran-3-carboxamides have been prepared by reaction of carbon suboxide with 2-hydroxyaryloximes.
Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: Biological activity and computational study
Chimenti, Franco,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Granese, Arianna,Befani, Olivia,Turini, Paola,Alcaro, Stefano,Ortuso, Francesco
, p. 3697 - 3703 (2004)
A series of coumarin-3-acyl derivatives have been synthesized and investigated for the ability to inhibit selectively monoamine oxidases. The coumarin-3-carboxylic acids, 2a-e, proved to be reversible and selective inhibitors of the MAO-B isoform, display
3 - Coumarin formic acid compound and application thereof as antibacterial agent for preparing plant pathogenic bacteria
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Paragraph 0039; 0044-0045; 0048-0049, (2021/03/24)
The invention relates to a compound with simple structure for inhibiting growth activity of phytopathogens, specifically relates to a 3-coumarin formic acid compound and application of the 3-coumarin formic acid compound as an antibacterial agent for preparing the phytopathogens, and discloses application of the 3-coumarin formic acid compound as the antibacterial agent for preparing the phytopathogens. The two 3-coumarin formic acid compounds has the following characteristics of molecular structure: the formulas are as shown in the specification, wherein R is hydrogen, methyl, methoxyl, hydroxyl, halogen and nitryl. The in vitro inhibitory activity of twenty-eight synthetic target compounds on four common plant pathogenic fungi such as apple decay pathogenic bacteria, apple ring spot pathogenic bacteria, maize curvularia pathogenic bacteria and potato dry rot pathogenic bacteria is measured by adopting a hypha linear growth rate method, so that the condition that all compounds have different inhibiting effects on supplied experimental bacteria is found.
Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin
Li, Wen-Bo,Qiao, Xue-Peng,Wang, Zi-Xiao,Wang, Shuai,Chen, Shi-Wu
, (2020/11/09)
Antioxidants have been the subject of intense research interest due to their numerous health benefits. In this work, a series of new conjugates of hydroxytyrosol and coumarin were synthesized and evaluated for their free radical scavenging, toxicity and antioxidant mechanism in vitro. The all target compounds 14a–t exhibited better radical scavenging activity than BHT, hydroxytyrosol, and coumarin in both DPPH radical and ABTS+ radical cation scavenging assays. The structure-activity relationships study indicated that the number and position of hydroxyl groups on the coumarin ring were vital to a good antioxidant capacity. Furthermore, the most promising compound 14q showed less toxicity in hemolysis assay and weaker antiproliferative effects than BHT against normal WI-38 and GES cells, and enhanced viability of H2O2-induced HepG2 cells. Additionally, 14q decreased the apoptotic percentage of HepG2 cells, reduced the ROS produce and LDH release, and improved GSH and SOD levels in H2O2-treated HepG2 cells. Lastly, 14q exhibited more stability than hydroxytyrosol in methanol solution. These results revealed that conjugations of hydroxytyrosol and coumarin show better antioxidant capacity, and are the efficacious approach to finding novel potential antioxidant.
Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity
Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Lv, Yangjing,Mi, Zhisheng,Shi, Yuan,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhou, Tao
, (2020/05/22)
A series of (3-hydroxypyridin-4-one)-coumarin hybrids were developed and investigated as potential multitargeting candidates for the treatment of Alzheimer's disease (AD) through the incorporation of iron-chelating and monoamine oxidase B (MAO-B) inhibition. This combination endowed the hybrids with good capacity to inhibit MAO-B as well as excellent iron-chelating effects. The pFe3+ values of the compounds were ranging from 16.91 to 20.16, comparable to more potent than the reference drug deferiprone (DFP). Among them, compound 18d exhibited the most promising activity against MAO-B, with an IC50 value of 87.9 nM. Moreover, compound 18d exerted favorable antioxidant activity, significantly reversed the amyloid-β1-42 (Aβ1-42) induced PC12 cell damage. More importantly, 18d remarkably ameliorated the cognitive dysfunction in a scopolamine-induced mice AD model. In brief, a series of hybrids with potential anti-AD effect were successfully obtained, indicating that the design of iron chelators with MAO-B inhibitory and antioxidant activities is an attractive strategy against AD progression.
