- Novel intramolecular charge transfer effect-based ligands and aggregation-induced emission-active europium complexes: synthesis, characterization, and fluorescence properties
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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.
- Yang, Shuaishuai,Guo, Zuping,Hu, Zhongqian,Guo, Dongcai
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- Et3N catalyzed cascade reaction of Meldrum’s acid with ortho-hydroxyaryl aldehydes for the synthesis of coumarin-3-carboxylic acids under solvent-less condition
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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.]
- Pan, Wan-Yü,Xiao, Yü-Meng,Xiong, Hou-Qing,Lü, Cheng-Wei
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- Novel coumarin-pyrazole carboxamide derivatives as potential topoisomerase II inhibitors: Design, synthesis and antibacterial activity
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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.
- Liu, Hao,Ren, Zi-Li,Wang, Wei,Gong, Jie-Xiu,Chu, Ming-Jie,Ma, Quan-Wei,Wang, Jie-Chun,Lv, Xian-Hai
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- Uncatalysed Production of Coumarin-3-carboxylic Acids: A Green Approach
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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.
- Martínez, Joel,Sánchez, Lilibeth,Pérez, F. Javier,Carranza, Vladimir,Delgado, Francisco,Reyes, Leonor,Miranda, René
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- Synthesis and biological evaluation of carvacrol-based derivatives as dual inhibitors of H. Pylori strains and ags cell proliferation
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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.
- 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
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- NOVEL REACTIONS OF CARBON SUBOXIDE. IV. SYNTHESIS OF SOME N-HYDROXY-2-OXO-2H-1-BENZOPYRAN-3-CARBOXAMIDES
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Some N-hydroxy-2-oxo-2H-1-benzopyran-3-carboxamides have been prepared by reaction of carbon suboxide with 2-hydroxyaryloximes.
- Bonsignore, Leonardo,Loy, Guiseppe,Secci, Mario
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- Inhibition of monoamine oxidases by coumarin-3-acyl derivatives: Biological activity and computational study
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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
- Chimenti, Franco,Secci, Daniela,Bolasco, Adriana,Chimenti, Paola,Granese, Arianna,Befani, Olivia,Turini, Paola,Alcaro, Stefano,Ortuso, Francesco
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- 3 - Coumarin formic acid compound and application thereof as antibacterial agent for preparing plant pathogenic bacteria
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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.
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Paragraph 0039; 0044-0045; 0048-0049
(2021/03/24)
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- Synthesis and antioxidant activity of conjugates of hydroxytyrosol and coumarin
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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.
- Li, Wen-Bo,Qiao, Xue-Peng,Wang, Zi-Xiao,Wang, Shuai,Chen, Shi-Wu
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- Rational design, synthesis and biological evaluation of novel multitargeting anti-AD iron chelators with potent MAO-B inhibitory and antioxidant activity
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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.
- Bai, Renren,Gu, Jinping,Guo, Jianan,Jiang, Xiaoying,Lv, Yangjing,Mi, Zhisheng,Shi, Yuan,Xie, Yuanyuan,Yao, Chuansheng,Zhang, Changjun,Zhou, Tao
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- Coumarin hybrid pyridinone amide derivative with potential anti-AD activity and preparation method and application of derivative
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The invention discloses a coumarin hybrid pyridinone amide derivative and a preparation method and application thereof. The coumarin hybrid pyridinone amide derivative and pharmacologically acceptablesalt thereof are shown in the formula (I) and the formula (II), and the derivative can be used for preparing drugs for resisting the Alzheimer's disease, the Parkinson's disease or treating other diseases or symptoms by suppressing monoamine oxidase, chelating metallic iron ions, resisting A and resisting oxidation.
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Paragraph 0189; 0193; 0194
(2020/02/27)
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- Novel coumarin-thiazolyl ester derivatives as potential DNA gyrase Inhibitors: Design, synthesis, and antibacterial activity
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The design and synthesis of novel coumarin-thiazolyl ester derivatives of potent DNA gyrase inhibitory activity were the main aims of this study. All the novel synthesized compounds were examined for their antibacterial activity against Staphylococcus aureus, Listeria monocytogenes, Escherichia coli and Salmonella. Compound 8p exhibited excellent antibacterial activity against four bacteria strains with MIC values of 0.05, 0.05, 8, and 0.05 μg/mL, respectively. In vitro drug-resistant bacterial inhibition experiments indicated that compound 8p exhibited the best bacteriostatic effect in the selected compounds and four positive control drugs with MIC values of 4 μg/mL. In vitro enzyme inhibitory assay showed that compound 8p exhibited potent inhibition against DNA gyrase with IC50 values of 0.13 μM. The molecular docking model indicated that compounds 8p can bind well to the DNA gyrase by interacting with amino acid residues. This study demonstrated that the compound 8p can act as the most potent DNA gyrase inhibitor in the reported series of compounds and provide valuable information for the commercial DNA gyrase inhibiting bactericides.
- Cheng, Xiang,Chu, Zhi-Wen,Hu, Rui,Liu, Hao,Lv, Xian-Hai,Xia, Dong-Guo
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- Peptides N-connected to hydroxycoumarin and cinnamic acid derivatives: Synthesis and fluorescence spectroscopic, antioxidant and antimicrobial properties
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The tripeptide Tyr-Gly-Ser and a series of conjugations to coumarin, cinnamic and gallic acid were synthesized in salt form and their antioxidant and antimicrobial activities were investigated. The N-connecting hydroxycoumarin, cinnamic and gallic acid derivatives to peptides and the use of BBr3 as a demethylating agent for peptides was reported. Their activities were investigated based on the conjugated moiety structures. Studies of their activities showed that conjugated tripeptides 7,8-dihydroxycoumarin-peptide (17), caffeic acid-peptide (22) and gallic acid-peptide (28) were found to be superior to ascorbic acid with respect to their antioxidant activity, and 12, 14, 24, and 25 exhibited the most antimicrobial activity in the series compared to amoxicillin. Additionally, the incredible florescence intensity and brightness of 17 in water and DMSO, compared to other synthesized compounds, qualified this peptide as a suitable probe in the human body.
- Ghalehshahi, Hajar G.,Balalaie, Saeed,Aliahmadi, Atousa
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p. 8831 - 8842
(2018/06/11)
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- Coumarins and adenosine receptors: New perceptions in structure–affinity relationships
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Adenosine receptor (AR) subtypes are involved in several physiological and pharmacological processes. Ligands that are able to selectively modulate one receptor subtype can delay or slow down the progression of diverse diseases. In this context, our research group focused its investigation into the discovery and development of novel, potent and selective AR ligands based on coumarin scaffold. Therefore, a series of 3-phenylcarboxamidocoumarins were synthesized and their affinity for the human AR subtypes was screened by radioligand binding assays for A1, A2A and A3 receptors and for A2B by adenylyl cyclase assay. Compound 26 was found to be the most remarkable, with a hA1/hA3 and hA2A/hA3 selectivity of 42, for the A3 AR (Ki?=?2.4?μm). Receptor-driven molecular modelling studies have provided valuable information on the binding/selectivity data of compound 26 and for the following optimization process. Moreover, compound 26 presents drug-like properties according to the general guidelines linked to the concept.
- Fonseca, André,Matos, Maria Jo?o,Vilar, Santiago,Kachler, Sonja,Klotz, Karl-Norbert,Uriarte, Eugenio,Borges, Fernanda
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p. 245 - 256
(2017/12/29)
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- Coumarin versus Chromone Monoamine Oxidase B Inhibitors: Quo Vadis?
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Because of the lack of significant disease-modifying drugs for neurodegenerative disorders, a pressing need for new chemical entities endowed with IMAO-B still exists. Within this framework, and for the first time, a study was performed to compare coumari
- Fonseca, André,Reis, Joana,Silva, Tiago,Matos, Maria Jo?o,Bagetta, Donatella,Ortuso, Francesco,Alcaro, Stefano,Uriarte, Eugenio,Borges, Fernanda
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supporting information
p. 7206 - 7212
(2017/09/07)
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- Exploring coumarin potentialities: Development of new enzymatic inhibitors based on the 6-methyl-3-carboxamidocoumarin scaffold
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Novel 6-methyl-3-carboxamidocoumarins (compounds 4-15) were synthesized by an effective three step synthetic strategy and screened towards MAO, AChE and BuChE enzymes. In general, the compounds act as selective MAO-B inhibitors. Compound 11 is highlighted as a potent (IC50hMAO-B = 4.66 nM), reversible and non-competitive MAO-B inhibitor.
- Fonseca,Matos,Reis,Duarte,Gutiérrez,Santana,Uriarte,Borges
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p. 49764 - 49768
(2016/07/06)
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- Potassium phosphate catalyzed efficient synthesis of 3-carboxycoumarins
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An efficient and rapid synthesis of 3-carboxycoumarins has been expediently accomplished by a reaction of salicylaldehyde with Meldrum's acid using potassium phosphate as an inexpensive catalyst at ambient temperature.
- Undale, Kedar A.,Gaikwad, Dipak S.,Shaikh, Tarannum S.,Desai, Uday V.,Pore, Dattaprasad M.
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experimental part
p. 1039 - 1042
(2012/10/08)
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- BITTER TASTE MODULATORS
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The present invention includes antagonists of human type 2 taste receptors (hT2Rs) having structural Formula (I). The present invention also provides compositions containing these antagonists, the use of these antagonists for modulating taste perception, particularly bitter taste, and the method of preparing these antagonists (I).
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Page/Page column 58
(2012/01/06)
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- Synthesis, selective anti-Helicobacter pylori activity, and cytotoxicity of novel N-substituted-2-oxo-2H-1-benzopyran-3-carboxamides
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N-substituted-3-carboxamido-coumarin derivatives were prepared and evaluated for selective antibacterial activity against 20 isolates of Helicobacter pylori clinical strains, including five metronidazole resistant ones. Some of them possessed the best activity against H. pylori metronidazole resistant strains with MIC values lower than the drug reference (metronidazole). Furthermore, anti-inflammatory activity through the inhibition of the IL-8 production was investigated.
- Chimenti, Franco,Bizzarri, Bruna,Bolasco, Adriana,Secci, Daniela,Chimenti, Paola,Granese, Arianna,Carradori, Simone,Rivanera, Daniela,Zicari, Alessandra,Scaltrito, M. Maddalena,Sisto, Francesca
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experimental part
p. 4922 - 4926
(2010/10/02)
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- COSMETIC OR DERMATOLOGICAL COMPOSITION COMPRISING A POLYMER BEARING JUNCTION GROUPS, AND COSMETIC TREATMENT PROCESS
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The present patent application relates to a cosmetic or dermatological composition comprising, in a cosmetically or dermatologically acceptable medium, a polymer comprising: (a) a polymer backbone that may be obtained by reaction: of a polyol comprising 3 to 6 hydroxyl groups;of a monocarboxylic acid containing 6 to 32 carbon atoms;of a polycarboxylic acid comprising at least two carboxylic groups COOH, and/or of a cyclic anhydride such as a polycarboxylic acid and/or of a lactone comprising at least one carboxylic group COOH; and(b) at least one junction group linked to the said polymer backbone and capable of establishing H bonds with one or more partner junction groups, each pairing of a junction group involving at least three H (hydrogen) bonds. The patent application also concerns a cosmetic treatment process using the said composition.
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- Novel 3-carboxamide-coumarins as potent and selective FXIIa inhibitors
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Recently, FXIIa was highlighted as an original attractive target for the development of new anticoagulant drugs with low rates of therapy-related hemorrhages. In this work, we describe the development of a new series of 3-carboxamide-coumarins that are the first potent and selective nonpeptidic inhibitors of FXIIa.
- Robert, Séverine,Bertolla, Carine,Masereel, Bernard,Dogné, Jean-Michel,Pochet, Lionel
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scheme or table
p. 3077 - 3080
(2009/04/07)
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- 3,6-Disubstituted coumarins as mechanism-based inhibitors of thrombin and factor Xa
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In this work, coumarins were screened on thrombin (THR) and factor Xa (FXa), two of the most promising targets for the development of anticoagulant drugs. This allowed us to highlight compound 30, characterized by a 2,5-dichlorophenyl ester in the 3-position and a chloromethyl moiety in the 6-position, as a very potent THR inhibitor (ki/KI = 37 000 M-1 s-1). Moreover, this compound exhibits good selectivity over FXa (168-fold) and trypsin (54-fold). The mechanism of inactivation was investigated in this series and significantly differs from that previously observed with α-chymotrypsin. Indeed, the addition of hydrazine on the THR-inhibitor complex promotes a partial induced THR reactivation. This reactivation, confirmed by LC/MS, showed the resurgence of the native THR and a new dihydrazide complex. Docking experiments were then efficiently used to explain the trends observed in the enzymatic assays as well as to corroborate the postulated inhibition mechanism. Finally, the cell permeability of our derivatives was estimated using a computational approach.
- Frédérick, Rapha?l,Robert, Séverine,Charlier, Caroline,De Ruyck, Jér?me,Wouters, Johan,Pirotte, Bernard,Masereel, Bernard,Pochet, Lionel
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p. 7592 - 7603
(2007/10/03)
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- COUMARIN DERIVATIVES, METHODS OF PREPARATION AND APPLICATION AND APPLICATION AS MEDICINES
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The invention concerns compounds of general formula (I) in which: X, X' and X" independently of each other represent O or S; Y represents O, S, NH or NHS; R 3 represents in particular a cycloalkyl group; R 5, R 6, R 7 and R 8 mutually identical or different, represent in particular hydrogen; a halogen atom. Said compounds can be used as active substances of medicines as inhibitors of protease. "
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