- Quantification of azide groups on a material surface and a biomolecule using a clickable and cleavable fluorescent compound
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Here, we propose a novel method for quantifying azide groups on a solid surface and a protein using a clickable and cleavable fluorescent compound. The clickable and cleavable fluorescent compound conjugates with the azide groups on the material surface a
- Sakai, Rika,Iguchi, Hiroki,Maruyama, Tatsuo
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- A Simple One-Pot Synthesis of Fully Substituted 1H-Pyridone[1,2-a]-Fused-1,3-Diazaheterocycles
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An efficient procedure for the synthesis of 7-(aryl)-8-nitro-2,3,6,7-tetrahydroimidazo[1,2-a]pyridinones, 8-(aryl)-9-nitro-3,4,7,8-tetrahydropyridone[1,2-a]pyrimidines and 9-(aryl)-10-nitro-2,3,4,5,8,9-hexahydropyridone[1,2-a]diazepine via one-pot three component reaction of diamine, nitroketene dithioacetal (1,1-bis(methylsulfanyl)-2-nitroethene), and coumarine-3- carboxylic acid derivatives in EtOH under reflux conditions is reported. The advantages of this procedure are simplicity, easy purification, good yields, and catalyst-free conditions. All products were confirmed by 1H- and 13C-NMR, IR, MS, and X-ray crystal structure analyses.
- Bayat, Mohammad,Rezaee, Monireh,Zhu, Long-Guan
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- ZrOCl2 · 8H2O: An efficient catalyst for rapid one-pot synthesis of 3-carboxycoumarins under ultrasound irradiation in water
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In this report, a rapid, efficient and environmental friendly synthesis of 3-carboxycoumarins under ultrasound irradiation in water media is described. The Knoevenagel condensation of Meldrum's acid with substituted benzaldehydes in the presence of zirconium oxide chloride (ZrOCl2·8H2O) and ultrasonic irradiation in water gave the corresponding 3-carboxycoumarins in good to excellent yields.
- Bardajee, Ghasem Rezanejade,Jafarpour, Farnaz,Afsari, Hamid Samareh
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- MESOMORPHIC HETEROCYCLIC HOMOLOGOUS SERIES: I. 7-(4 prime -n-ALKOXYBENZOYLOXY)-3-ACETYLCOUMARINS II. 4 prime -FORMYLPHENYL 7-n-ALKOXYCOUMARIN-3-CARBOXYLATES.
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Two homologous series of coumarin derivatives have been synthesized and mesomorphic behavior of their members has been studied. In case of Series I, mesomorphism does not begin to appear until the butyl homolog, which is monotropic nematic. The remaining
- Trivedi,Thaker
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- A practical and environmentally friendly preparation of 3-carboxycoumarins
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The condensation of salicylaldehydes with Meldrum's acid in water at 75°C to produce 3-carboxycoumarin derivatives is described.
- Deshmukh,Burud, Rahila,Baldino, Carmen,Chan, Philip C. M.,Liu, Jifeng
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- Silica sulfuric acid: A versatile and reusable catalyst for synthesis of coumarin-3-carboxylic acids in a solventless system
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Synthesis of substituted coumarin-3-carboxylic acid via Knoevenagel condensation of meldrum's acid with ortho-hydroxyaryl aldehydes in solventless system is described.
- Hekmatshoar, Rahim,Rezaei, Akram,Beheshtiha, S. Y. Shirazi
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- Solid phase synthesis of substituted coumarin-3-carboxylic acids via the Knoevenagel condensation
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A solid phase synthesis of substituted coumarin-3-carboxylates using the Knoevenagel condensation reaction between ethyl malonate bound to the Wang resin and ortho-hydroxyarylaldehydes is described. The reaction has been shown to proceed cleanly to give the desired products.
- Watson, Brett T.,Christiansen, Gerda E.
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- Synthesis of new fluorophores derived from monoazacrown ethers and coumarin nucleus
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New ionophores derived from azacrown ethers attached to coumarins have been synthesized and characterized. The alkaline-earth complexes of these new ligands were studied from their UV-vis, NMR, and fluorescence data. Some systems displayed bathochromic shifts and fluorescence decreases upon complexation with Ca2+ that may make them useful signaling devices of this metal.
- Brunet, Ernesto,Garcia-Losada, Pablo,Rodriguez-Ubis, Juan-Carlos,Juanes, Olga
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- A convenient synthesis of coumarin-3-carboxylic acids via Knoevenagel condensation of Meldrum's acid with ortho-hydroxyaryl aldehydes or ketones
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Coumarin-3-carboxylic acids were obtained in high yields with excellent purity from ortho-hydroxybenzaldehydes and Meldrum's acid after a 2 h reflux in ethanol. The less reactive ketones were first reacted with alcoholic ammonia to form ketimines, which were then condensed with Meldrum's acid to generate 4-alkylcoumarin-3-carboxylic acids in moderate yields.
- Song, Aimin,Wang, Xiaobing,Lam, Kit S.
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- Preparation and application of Sigma-2 fluorescent ligand
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The invention mainly relates to synthesis of a series of sigma-2 fluorescent ligands and application of the sigma-2 fluorescent ligands in the fields of pharmacy and medicine, specifically to a series of compounds containing benzopyran structures, wherein the compounds have high affinity activity and selectivity to a sigma-2 receptor, have good affinity activity to the sigma-2 receptor, and have diagnosis and treatment effects on tumor cells, brain cells of patients with Alzheimer's disease, and other cells highly expressing the sigma-2 receptor.
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Paragraph 0070-0074
(2021/06/06)
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- Method for synthesizing coumarin-3-carboxylic acid compounds by one-pot two-step method
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The invention relates to a method for synthesizing coumarin-3-carboxylic acid compounds by a one-pot two-step method. The structural formula of the coumarin-3-carboxylic acid compounds is shown in the description, wherein R1 is H , Cl , Br, NO2 , CH3 and HO . According to the synthesis process of the coumarin-3-carboxylic acid compounds, malonic acid, acetone and substituted salicylaldehyde serve as raw materials, iodine serves as a catalyst, acetic anhydride serves as a solvent, a series of coumarin-3-carboxylic acid compounds are synthesized through a one-pot cascade reaction, and the efficiency and the yield are greatly improved compared with a fractional step method.
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Paragraph 0053; 0056; 0058; 0073; 0079; 0084-0090
(2021/06/12)
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- Green synthesis method of coumarin-3-carboxylic acid compound
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The invention relates to a green synthesis method of a coumarin-3-carboxylic acid compound. The synthesis process of the coumarin-3-carboxylic acid compound is as follows: R1 is H, Cl, Br, NO2, CH3 and HO. A series of coumarin-3-carboxylic acid compounds are synthesized in one step without a catalyst by taking R1-substituted salicylaldehyde and Meldrum's acid as raw materials and water as a reaction medium, the process steps are simple, the method has universality, reaction liquid can be repeatedly added for reaction, no waste or waste liquid is generated, the yield of a target product is greater than 54.3%, and the method is an environment-friendly green synthesis method.
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Paragraph 0053-0061; 0073
(2021/06/26)
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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; 0050-0051
(2021/03/24)
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- MODULAR CHEMICAL PROBE FOR DETECTION OF AMINO ACID CITRULLINE IN PHYSIOLOGICAL SAMPLES
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An improved chemical probe for the detection of the amino acid citrulline combines: 1) a reactive head formed of 1,3-dicarbonyl moiety that reacts with a citrulline side chain in an improved manner compared to currently used 1,2-dicarbonyl moieties; and 2) a modular action of the probe where citrulline side chains are labeled first using reactive heads described above, and attachment of a read-out subunit or tag, be it a fluorophore, a nanoparticle, or an antigen is performed separately. The modular nature of the chemical probe increases the sensitivity of the probes due to their smaller size. Additionally, the chemical probes of the present disclosure allow the same sample to be analyzed using a variety of read-out methods.
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(2021/01/29)
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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 0098; 0102; 0103
(2020/02/27)
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- Design, synthesis and biological evaluation of coumarin-based N-hydroxycinnamamide derivatives as novel histone deacetylase inhibitors with anticancer activities
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A series of novel coumarin-based N-hydroxycinnamamide derivatives were designed and synthesized as histone deacetylase (HDAC) inhibitors. Most of the synthesized compounds showed potent HDAC inhibitory activity and significant antiproliferative activity a
- Cheng, Maojun,Ding, Jiaoli,Fang, Yuanying,Guan, Zhiyu,Guo, Jie,Jin, Yi,Liu, Jing,Wan, Yang,Wang, Rikang,Xie, Sai-Sai,Zhang, Zhipeng
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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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- 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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- Synthesis of coumarin analogs appended with quinoline and thiazole moiety and their apoptogenic role against murine ascitic carcinoma
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The synthesis and antiproliferative effect of a series of quinoline and thiazole containing coumarin analogs 12a-d and 13a-f respectively, on mice leukemic cells was performed. The chemical structures of newly synthesized compounds were confirmed by IR, 1H NMR, 13C NMR and mass spectral analysis. The result indicates that, 7-methoxy-2-oxo-2H-chromene-3-carboxylic acid [4-(4-methoxy-phenyl)-thiazol-2-yl]-amide (13f) showed potent activity against EAC and DLA cells in MTT (15.3 μM), tryphan blue (15.6 μM) and LDH (14.2 μM) leak assay with 5-fluorouracil as a standard. Further, the anti-neoplastic effect of the compound 13f was verified against Ehrlich ascites tumour by BrdU incorporation, TUNEL, FACS and DNA fragmentation assays. Experimental data showed that compound 13f induces the apoptotic cell death by activating apoptotic factors such as caspase-8 &-3, CAD, Cleaved PARP, γ-H2AX and by degrading genomic DNA of cancer cells and thereby decreasing the ascitic tumour development in mice. Besides, compound 13f was also subjected for docking studies to approve the in vitro and in vivo studies. The data revealed that the compound 13f has very good interaction with caspase 3 protein by binding with amino acid Arg 207 through hydrogen bond.
- Prashanth,Avin, B.R. Vijay,Thirusangu, Prabhu,Ranganatha, V. Lakshmi,Prabhakar,Sharath Chandra, J.N. Narendra,Khanum, Shaukath Ara
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- Antifungal activity, mode of action variability, and subcellular distribution of coumarin-based antifungal azoles
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Azole antifungals inhibit the biosynthesis of ergosterol, the fungal equivalent of cholesterol in mammalian cells. Here we report an investigation of the activity of coumarin-substituted azole antifungals. Screening against a panel of Candida pathogens, including a mutant lacking CYP51, the target of antifungal azoles, revealed that this enzyme is inhibited by triazole-based antifungals, whereas imidazole-based derivatives have more than one mode of action. The imidazole-bearing antifungals more effectively reduced trailing growth associated with persistence and/or recurrence of fungal infections than triazole-based derivatives. The imidazole derivatives were more toxic to mammalian cells and more potently inhibited the activity of CYP3A4, which is one of the main causes of azole toxicity. Using live cell imaging, we showed that regardless of the type of azole ring fluorescent 7-diethylaminocoumarin-based azoles localized to the endoplasmic reticulum, the organelle that harbors CYP51. This study suggests that the coumarin is a promising scaffold for development of novel azole-based antifungals that effectively localize to the fungal cell endoplasmic reticulum.
- Elias, Rebecca,Benhamou, Raphael I.,Jaber, Qais Z.,Dorot, Orly,Zada, Sivan Louzoun,Oved,Pichinuk, Edward,Fridman
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p. 779 - 790
(2019/07/10)
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- FLUORESCENT PRODRUGS
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The invention provides a drug conjugate comprising: 1) a therapeutic agent that comprises a phosphate, phosphonate, carboxy, or phosphoramidate group, and 2) a fluorescent group linked to the phosphate, phosphonate, carboxy, or phosphoramidate group to form the corresponding ester and salts thereof. The conjugates are useful for therapy and as probes. The invention also provides therapeutic methods for treating diseases with conjugates of the invention as well as methods for determining optimal dosages of a conjugate or a therapeutic agent for a given patient using a conjugate of the invention
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Paragraph 0047-0048
(2018/08/12)
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- Design and synthesis of novel Vitamin D-coumarin hybrids using microwave irradiation
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A series of novel vitamin D-coumarin hybrids were synthesised by esterification of the corresponding coumarin-3-carboxylic acids and vitamin D or vitamin D CD-ring alcohol in CH2Cl2 under microwave irradiation. They were obtained in higher yields (from 64-81% up to 79-87%) and shorter reaction time (from 3 h down to 15 min), compared with earlier conventional methodologies. The structures of all the target compounds were confirmed by 1H NMR, 13C NMR and HRMS. This provides an attractive and alternative method for the preparation of high-value vitamin D-coumarin hybrids.
- Zhang, Hengrui,Fang, Zhijie
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p. 684 - 687
(2018/01/08)
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- Design, synthesis and biological evaluation of novel coumarin-based benzamides as potent histone deacetylase inhibitors and anticancer agents
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Histone deacetylases (HDACs) are attractive therapeutic targets for the treatment of cancer and other diseases. It has four classes (I-IV), among them especially class I isozyme are involved in promoting tumor cells proliferation, angiogenesis, differentiation, invasion and metastasis and also viable targets for cancer therapeutics. A novel series of coumarin-based benzamides was designed and synthesized as HDAC inhibitors. The cytotoxic activity of the synthesized compounds (8a-u) was evaluated against six human cancer cell lines including HCT116, A2780, MCF7, PC3, HL60 and A549 and a single normal cell line (Huvec). We evaluated their inhibitory activities against pan HDAC and HDAC1 isoform. Four compounds (8f, 8q, 8r and 8u) showed significant cytotoxicity with IC50 in the range of 0.53–57.59?μM on cancer cells and potent pan-HDAC inhibitory activity (consists of HDAC isoenzymes) (IC50?=?0.80–14.81?μM) and HDAC1 inhibitory activity (IC50?=?0.47–0.87?μM and also, had no effect on Huvec (human normal cell line) viability (IC50?>?100?μM). Among them, 8u displayed a higher potency for HDAC1 inhibition with IC50 value of 0.47?±?0.02?μM near equal to the reference drug Entinostat (IC50?=?0.41?±?0.06?μM). Molecular docking studies and Molecular dynamics simulation of compound 8a displayed possible mode of interaction between this compound and HDAC1enzyme.
- Abdizadeh, Tooba,Kalani, Mohammad Reza,Abnous, Khalil,Tayarani-Najaran, Zahra,Khashyarmanesh, Bibi Zahra,Abdizadeh, Rahman,Ghodsi, Razieh,Hadizadeh, Farzin
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- Fluorogenic probes to monitor cytosolic phospholipase A2 activity
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Arachidonic acid derivatives equipped with either one or two fluorescent groups attached to the tip of the alkyl chains were synthesized and shown to function as inhibitor and substrate probes of cPLA2. The inhibitor probe was demonstrated to p
- Ng, Cheng Yang,Kwok, Timothy Xiong Wei,Tan, Francis Chee Kuan,Low, Chian-Ming,Lam, Yulin
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p. 1813 - 1816
(2017/02/10)
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- Silver-Mediated Oxidative Decarboxylative Trifluoromethylthiolation of Coumarin-3-carboxylic Acids
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The introduction of trifluoromethylthio groups into organic compounds, in particular heterocycles, is important because of the prevalence of these structures in medicinally and agriculturally relevant molecules. Herein, the silver-mediated oxidative decarboxylative trifluoromethylthiolation of coumarin-3-carboxylic acids is reported. This methodology utilizes existing carboxylic acid functionalities for the direct conversion to CF3S groups and results in a broad scope of 3-trifluoromethylthiolated coumarins, including analogues of natural products, in moderate to excellent yields.
- Li, Minghao,Petersen, Jeffrey L.,Hoover, Jessica M.
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supporting information
p. 638 - 641
(2017/02/10)
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- Coumarin-based fluorogenic agents and uses thereof for specific protein labelling
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There are provided fluorescent labelling agents comprising a dimaleimide core connected to a fluorophore, processes for preparation thereof, and uses thereof for labelling and/or detection of specific protein targets. Fluorescent labelling agents comprising a compound having the structure of Formula I, and salts thereof, are described.
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Page/Page column 38-40
(2017/08/08)
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- SULFONATE COMPOUND, PHOTOACID GENERATOR, AND RESIN COMPOSITION FOR PHOTOLITHOGRAPHY
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Provided are: a non-ionic photoacid generator containing a sulfonate compound having a high photosensitivity to i lines, exhibiting excellent heat-resistance stability, and exhibiting excellent solubility in a hydrophobic material; and a resin composition
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Paragraph 0154
(2017/09/02)
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- Synthesis and anticholinesterase activity of coumarin-3-carboxamides bearing tryptamine moiety
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A number of N-(2-(1H-indol-3-yl)ethyl)-2-oxo-2H-chromene-3-carboxamides were synthesized and tested against AChE and BuChE. The in?vitro assessment of the synthesized compounds 4a-o revealed that most of them had significant activity toward AChE. The SAR study demonstrated that the introduction of benzyloxy moiety on the 7-position of coumarin scaffold can improve the anti-AChE activity. The best result was obtained with 7-(4-fluorobenzyl)oxy moiety in the case of compound 4o, displaying IC50value of 0.16?μM. Based on the docking study of AChE, the prototype compound 4o was laid across the active site and occupied both peripheral anionic site (PAS) and catalytic anionic site (CAS).
- Ghanei-Nasab, Samaneh,Khoobi, Mehdi,Hadizadeh, Farzin,Marjani, Azam,Moradi, Alireza,Nadri, Hamid,Emami, Saeed,Foroumadi, Alireza,Shafiee, Abbas
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- Design, synthesis and biological evaluation of coumarin derivatives as novel acetylcholinesterase inhibitors that attenuate H2O2-induced apoptosis in SH-SY5Y cells
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A novel series of coumarin derivatives were designed, synthesized and investigated for inhibition of cholinesterase, including acetyl cholinesterase (AChE) and butyrylcholinesterase (BuChE). This biological study showed that these compounds containing piperazine ring had significant inhibition activities on AChE rather than BuChE. Further study suggested that 9x, as one of this kind of structure derivative, showed the strongest inhibition activity on AChE with an IC50 value of 34?nM. Moreover, molecular docking, flow cytometry (FCM), and western blot assay suggested that 9x could induce cytoprotective autophagy to attenuate H2O2-induced cell death in human neuroblastoma SH-SY5Y cells. These findings highlight a new approach for the development of a novel potential neuroprotective compound targeting AChE with autophagy-inducing activity in future Alzheimer's disease (AD) therapy.
- Yao, Dahong,Wang, Jing,Wang, Guan,Jiang, Yingnan,Shang, Lei,Zhao, Yuqian,Huang, Jian,Yang, Shilin,Wang, Jinhui,Yu, Yamei
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p. 112 - 123
(2016/08/01)
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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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p. 7057 - 7063
(2016/08/25)
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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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- Fluorescently Labeled Amino Acids as Building Blocks for Bioactive Molecules
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A series of twelve fluorescently labeled amino acids were designed by assembling different coumarin, fluorescein, or nitrobenzo-furazan fluorophores with N-protected lysine or 2-aminopropionic acid. The synthesized amino acids were evaluated with regard to their spectroscopic properties. The easy introduction of the amino acids into peptides and peptidomimetics was exemplarily shown for one coumarin-labeled- amino acid.
- H?u?ler, Daniela,Gütschow, Michael
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p. 245 - 255
(2016/01/15)
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- Design, Synthesis, and in Vitro Evaluation of Novel 3, 7-Disubstituted Coumarin Derivatives as Potent Anticancer Agents
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Twenty-seven 3, 7-disubstituted coumarin derivatives were designed, synthesized, and evaluated in vitro as anticancer agents. Most of the compounds showed moderate-to-potent antiproliferative activity against K562 cells. Compounds 7b and 7d were chosen to evaluate the concentration of 50% growth inhibition (GI50) against SN12C, OVCAR, BxPC-3, KATO-III, T24, SNU-1, WiDr, HeLa, K562, and AGS cell lines. The most potent compound 7d was selected for further cell cycle arrest assay in the AGS cell line. The in vitro data indicated that methylation of benzimidazole moiety at the 3-position of coumarin exhibited significant enhancement of anticancer activity. This study should provide important information for further modification and optimization of coumarin derivatives as anticancer agents.
- Wang, Yubin,Liu, Haitao,Lu, Peng,Mao, Rui,Xue, Xiaojian,Fan, Chen,She, Jinxiong
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p. 637 - 647
(2015/03/14)
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- 3-CARBOXY SUBSTITUTED COUMARIN DERIVATIVES WITH A POTENTIAL UTILITY FOR THE TREATMENT OF CANCER DISEASES
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The present invention relates to novel compounds. The present invention also relates to the compounds for use as a medicine, more in particular for the prevention or treatment of cancer, more in particular cancers expressing MCT1 and/or MCT4. The present invention also relates to a method for the prevention or treatment of cancer in animals or humans by using the novel compounds. The present invention furthermore relates to pharmaceutical compositions or combination preparations of the novel compounds and to the compositions or preparations for use as a medicine, more preferably for the prevention or treatment of cancer. The present invention also relates to processes for the preparation of the compounds.
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Page/Page column 75; 76
(2015/01/06)
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- Synthesis and pharmacological evaluation of carboxycoumarins as a new antitumor treatment targeting lactate transport in cancer cells
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Under hypoxia, cancer cells consume glucose and release lactate at a high rate. Lactate was recently documented to be recaptured by oxygenated cancer cells to fuel the TCA cycle and thereby to support tumor growth. Monocarboxylate transporters (MCT) are the main lactate carriers and therefore represent potential therapeutic targets to limit cancer progression. In this study, we have developed and implemented a stepwise in vitro screening procedure on human cancer cells to identify new potent MCT inhibitors. Various 7-substituted carboxycoumarins and quinolinone derivatives were synthesized and pharmacologically evaluated. Most active compounds were obtained using a palladium-catalyzed Buchwald-Hartwig type coupling reaction, which proved to be a quick and efficient method to obtain aminocarboxycoumarin derivatives. Inhibition of lactate flux revealed that the most active compound 19 (IC 50 11 nM) was three log orders more active than the CHC reference compound. Comparison with warfarin, a conventional anticoagulant coumarin, further showed that compound 19 did not influence the prothrombin time which, together with a good in vitro ADME profile, supports the potential of this new family of compounds to act as anticancer drugs through inhibition of lactate flux.
- Draoui, Nihed,Schicke, Olivier,Fernandes, Antony,Drozak, Xavier,Nahra, Fady,Dumont, Amélie,Douxfils, Jonathan,Hermans, Emmanuel,Dogné, Jean-Michel,Corbau, Romu,Marchand, Arnaud,Chaltin, Patrick,Sonveaux, Pierre,Feron, Olivier,Riant, Olivier
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p. 7107 - 7117
(2013/11/06)
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- Novel coumarin-3-carboxamides bearing N-benzylpiperidine moiety as potent acetylcholinesterase inhibitors
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Abstract Some novel coumarin-3-carboxamide derivatives linked to N-benzylpiperidine scaffold were synthesized and evaluated as acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) inhibitors. The screening results showed that most of compounds exhibited potent anti-AChE activity in the range of nM concentrations. Among them, compound 10c bearing an N-ethylcarboxamide linker and a 6-nitro substituent showed the most potent activity (IC50 = 0.3 nM) and the highest selectivity (SI = 26,300). Compound 10c was 46-fold more potent than standard drug donepezil against AChE. The kinetic study revealed that compound 10c exhibited mixed-type inhibition against AChE. Protein-ligand docking study demonstrated that the target compounds have dual binding site interaction mode and these results are in agreement with kinetic study.
- Asadipour, Ali,Alipour, Masoumeh,Jafari, Mona,Khoobi, Mehdi,Emami, Saeed,Nadri, Hamid,Sakhteman, Amirhossein,Moradi, Alireza,Sheibani, Vahid,Homayouni Moghadam, Farshad,Shafiee, Abbas,Foroumadi, Alireza
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p. 623 - 630
(2013/12/04)
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- Rapid synthesis of novel and known coumarin-3-carboxylic acids using stannous chloride dihydrate under solvent-free conditions
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Various coumarin-3-carboxylic acid (=2-oxo-2H-1-benzopyran-3-carboxylic acid; CcaH) derivatives have been synthesized in good yields using catalytic amounts of SnCl2·2 H2O under solvent-free conditions. This inexpensive, nontoxic, and readily available catalytic system (10 mol-%) efficiently catalyzes the Knoevenagel condensation and intramolecular cyclization of various 2-hydroxybenzaldehydes or acetophenones with Meldrum's acid. High product yields, use of inexpensive and safe catalyst, and solvent-free conditions display both economic and environmental advantages. Copyright
- Karami, Bahador,Farahi, Mahnaz,Khodabakhshi, Saeed
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experimental part
p. 455 - 460
(2012/05/04)
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- Synthesis and Biological Evaluation of Coumarin Derivatives as Inhibitors of Mycobacterium bovis (BCG)
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The coumarin compounds are an important class of biologically active molecules, which have attractive caught the attention of many organic and medicinal chemists, due to potential pharmaceutical implications and industrial applications. We herein report t
- Rezayan, Ali Hossein,Azerang, Parisa,Sardari, Soroush,Sarvary, Afshin
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p. 929 - 936,8
(2020/08/24)
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- Synthesis and selective human monoamine oxidase inhibition of 3-carbonyl, 3-acyl, and 3-carboxyhydrazido coumarin derivatives
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Several 3-carbonyl (1-26), 3-acyl (27-52), and 3-carboxyhydrazido (53-58) coumarins have been synthesized in high yields (72-99%) and tested in vitro for their human monoamine oxidase A and B (hMAO-A and hMAO-B) inhibitory activity. Different substituents on the coumarin nucleus were evaluated for their effect on biological activity and isoform selectivity. Substitution at position C7 of the 3-ethyl ester coumarin ring, or the introduction of a hydrazido substituent at C3, were important to obtain highly potent and selective hMAO-B inhibitors with IC50 values in the nanomolar range. Some derivatives were also submitted to a stability test and showed no chemical cleavage in vitro.
- Secci, Daniela,Carradori, Simone,Bolasco, Adriana,Chimenti, Paola,Yá?ez, Matilde,Ortuso, Francesco,Alcaro, Stefano
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p. 4846 - 4852
(2011/11/13)
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- Dramatic increase of quench efficiency in "spacerless" dimaleimide fluorogens
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In this post-genomic era, new techniques are needed to cope with the task of assigning functional roles to the huge number of identified putative gene products. We have developed a minimalist labelling strategy based on the use of synthetic fluorogenic probe reagents that fluoresce only after their reaction with a target peptide sequence. The probe reagents have fluorescent cores and bear two maleimide groups, such that their latent fluorescence is quenched by a photoinduced electron transfer (PET) to the pendant maleimide groups, until both of these groups undergo a specific thiol addition reaction. The efficiency of the fluorescence quenching is critical to the practicality of this labelling method, and has been predicted to be related to the intramolecular distance between the fluorophore and the maleimide groups. We have conducted the first direct test of this hypothesis by preparing a series of novel fluorogens that differ only by the spacer moiety separating their coumarin fluorophore and their dimaleimide fragment. A striking correlation was observed between intramolecular distance and the fluorescence enhancement (FE) observed after reaction with two equivalents of thiol. Guided by this observation, we then designed 'spacerless' fluorogens, of which a dansyl derivative shows an FE ratio of >300, the largest recorded for dimaleimide fluorogens. The trends observed herein provide valuable lessons for subsequent fluorogen design, and the novel fluorogens developed in the course of this study are currently being applied to protein labelling applications.
- Caron, Karine,Lachapelle, Virginie,Keillor, Jeffrey W.
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experimental part
p. 185 - 197
(2011/02/23)
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- Synthesis and evaluation of self-calibrating ratiometric viscosity sensors
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We describe the design, synthesis and fluorescent profile of a family of self-calibrating dyes that provide ratiometric measurements of fluid viscosity. The design is based on covalently linking a primary fluorophore (reference) that displays a viscosity-independent fluorescence emission with a secondary fluorophore (sensor) that exhibits a viscosity-sensitive fluorescence emission. Characterization of fluorescent properties was made with separate excitation of the units and through Resonance Energy Transfer from the reference to the sensor dye. The chemical structures of both fluorophores and the linker length have been evaluated in order to optimize the overall brightness and sensitivity of the viscosity measurements. We also present an application of such ratiometric dyes for the detection of membrane viscosity changes in a liposome model.
- Yoon, Hyung-Jo,Dakanali, Marianna,Lichlyter, Darcy,Chang, Willy M.,Nguyen, Karen A.,Nipper, Matthew E.,Haidekker, Mark A.,Theodorakis, Emmanuel A.
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supporting information; experimental part
p. 3530 - 3540
(2011/06/25)
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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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- 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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- Design, synthesis, physicochemical properties, and evaluation of novel iron chelators with fluorescent sensors
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The synthesis of a range of novel 3-hydroxypyridin-4-ones and 3-hydroxypyran-4-ones linked with different coumarin substituents is described. These compounds have been developed in order to provide a series of molecular probes for the quantification of intracellular labile iron pools. An evaluation of the effect of iron(III) on fluorescence intensity was undertaken. Chelation of iron(III) causes quenching of fluorescence. The relationship between iron(III) concentration and the extent of fluorescence quenching indicates that the metal is chelated in a complex with a metal-to-ligand stoichiometry of 1:3. The fluorescence of hydroxypyridinone compounds was found to be more efficiently quenched by iron(III) than were the hydroxypyranones. The metal-to-ligand stoichiometry at which maximum quenching is observed was found to depend on the site at which coumarin is attached. The efficiency of fluorescence quenching by iron(III) is markedly influenced by solvent polarity and pH. The permeability of two representative fluorescent chelators across human erythrocyte ghost membranes was investigated. The rate of permeability for a series of probes was found to be related to the corresponding ClogP values.
- Ma, Yongmin,Luo, Wei,Quinn, Peter J.,Liu, Zudong,Hider, Robert C.
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p. 6349 - 6362
(2007/10/03)
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- One-Pot Synthesis of 3-Carboxycoumarins via Consecutive Knoevenagel and Pinner Reactions in Water
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Chloro-, hydroxy-, methoxy-, and tert-butyl-substituted 3-carboxycoumarins have been prepared by one-pot procedure by reaction of suitably substituted salicylaldehydes with malononitrile in water. The over-all yields are high and the protocol does not require organic solvents.
- Fringuelli, Francesco,Piermatti, Oriana,Pizzo, Ferdinando
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p. 2331 - 2334
(2007/10/03)
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- An efficient solid-phase synthesis of 3-carboxycoumarins based on a scaffold-polymerbound cyclic malonic ester
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The condensation of substituted o-methoxybenzaldehydes or o-hydroxybenzaldehydes with a resin-bound cyclic malonic ester 3 afforded the resin 4 without catalyst. Cyclisation of the resin 4 in sulfuric acid formed 3-carboxycoumarins in good yield and excellent purity.
- Tang, Jing,Huang, Xian
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p. 354 - 355
(2007/10/03)
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- Synthesis of Coumarin-3-O-acylisoureas by Dicyclohexylcarbodiimide
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The synthesis and isolation of some O-acylisoureas are described.The reaction between dicyclohexylcarbodiimide and coumarin-3-carboxylic acids leads to coumarin-dicyclohexylisourea derivatives, isolated as the main products, and to coumarin-dicyclohexylur
- Bonsignore, Leonardo,Cottiglia, Filippo,Maccioni, Anna M.,Secci, Daniela,Lavagna, Silvio M.
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p. 573 - 578
(2007/10/02)
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- A One-Pot Synthesis of Coumarins from Dipotassium O-Methoxybenzylidenemalonates
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o-Methoxybenzylidenemalonates 1, which are available from o-methoxybenzaldehydes and diethylmalonate, were hydrolysed to the dipotassium malonates 2.Treatment of the salts 2 with trifluoroacetic acid-trifluoroacetic anhydride gave the title coumarins by a demethylative ring-closure reaction in 60-80percent yield.
- Hormi, Osmo E.O.,Peltonen, Carita,Bergstroem, Riitta
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p. 219 - 222
(2007/10/02)
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- SYNTHESIS OF 3-CARBOXYCOUMARINS FROM O-METHOXYBENZYLIDENE MELDRUM'S ACID DERIVATIVES
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Reaction of o-methoxybenzaldehydes with Meldrum's acid followed by cyclization in sulfuric acid of the benzylidene derivatives 3a-g affords 3-carboxycoumarins in excellent yields.
- Armstrong, Veronica,Soto, Oriana,Valderrama, Jaime A.,Tapia, Ricardo
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p. 717 - 726
(2007/10/02)
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