4377-33-7Relevant academic research and scientific papers
Design and synthesis of a cyclitol-derived scaffold with axial pyridyl appendages and its encapsulation of the silver(I) cation
Leo, Pierre-Marc,Morin, Christophe,Philouze, Christian
, p. 1022 - 1024 (2010)
Conversion of a myo-inositol derivative into a scyllo-inositol-derived scaffold with C3ν symmetry bearing three axial pyridyl appendages is presented. This pre-organized hexadentate ligand allows complexation of silver(I). The crystal structure of the complex was established.
Fabrication and covalent modification of highly chelated hybrid material based on silica-bipyridine framework for efficient adsorption of heavy metals: Isotherms, kinetics and thermodynamics studies
Radi, Smaail,Tighadouini, Said,Bacquet, Maryse,Degoutin, Stéphanie,Janus, Ludovic,Mabkhot, Yahia N.
, p. 82505 - 82514 (2016)
Adsorbent materials are essential in clean-up processes. Research of efficient materials is a well-established technology. In this work, a novel and excellent host for heavy metals was synthesized by covalent immobilization of bipyridine tripodal receptor onto silica particles. The new engineered surface was well analyzed and evaluated by BET, BJH, EA, FT-IR, SEM, TGA and solid-state 13C NMR. The adsorption properties were investigated using Pb(ii), Cd(ii), Zn(ii) and Cu(ii) metals by varying all relevant parameters such as pH, contact time, concentration, thermodynamic parameters, kinetics, Langmuir and Freundlich isotherms, etc. The hybrid material has been found to exhibit high distribution coefficients for heavy metals. Adsorption kinetics follows a pseudo-second-order model, as a rapid process as evidenced by equilibrium achieved within 20 min. The resulting adsorption isotherms of the material were better represented by the Langmuir model than the Freundlich model. The thermodynamic parameters (ΔH°, ΔS° and ΔG°) revealed that the adsorption was endothermic and spontaneous. In addition, the proposed material demonstrates a high degree of reusability over a number of cycles, thus enhancing its potential for application in heavy metals recycling. All metal ions were determined by atomic absorption measurements.
2-(N-Methylbenzyl)pyridine: A Potential Liquid Organic Hydrogen Carrier with Fast H2 Release and Stable Activity in Consecutive Cycles
Oh, Jinho,Jeong, Kwanyong,Kim, Tae Wan,Kwon, Hyunguk,Han, Jeong Woo,Park, Ji Hoon,Suh, Young-Woong
, p. 661 - 665 (2018)
The liquid organic hydrogen carrier (LOHC) 2-(N-methylbenzyl)pyridine (MBP) shows good potential for H2 storage based on reversible hydrogenation and dehydrogenation, with an H2 storage density of 6.15 wt %. This material and the corresponding perhydro product (H12-MBP) are liquids at room temperature. Remarkably, H2 release is much faster from H12-MBP over Pd/C than from the benchmark perhydro benzyltoluene over Pt/C at lower temperatures than 270 °C, owing to the addition of N atom into the benzene ring. Since this positive effect is unfavorable to the hydrogenation reaction, more Ru/Al2O3 catalyst or prolonged reaction time must be applied for complete H2 storage. Experiments with repeated hydrogenation–dehydrogenation cycles reveal that reversible H2 storage and release are possible without degradation of the MBP/H12-MBP pair. The prepared MBP satisfies the requirements for chemical stability, handling properties, and cytotoxicity testing.
Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors
Yan, Yu-Hang,Li, Wenfang,Chen, Wei,Li, Chao,Zhu, Kai-Rong,Deng, Ji,Dai, Qing-Qing,Yang, Ling-Ling,Wang, Zhenling,Li, Guo-Bo
, (2021/11/17)
Production of metallo-β-lactamases (MBLs) in bacterial pathogens is an important cause of resistance to the ‘last-resort’ carbapenem antibiotics. Development of effective MBL inhibitors to reverse carbapenem resistance in Gram-negative bacteria is still needed. We herein report X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives by considering how to engage with the active-site flexible loops and improve penetration into Gram-negative bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallographic analyses. Of the tested ICA inhibitors, 55 displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clinically isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphologic and internal structural changes of bacterial cells after treatment further demonstrated that 55 crossed the outer membrane and reversed the activity of meropenem. Moreover, 55 showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-negative carbapenem resistance.
Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications
Li, Hao,Nie, Fang-Yuan,Song, Qin-Hua,Xia, Hong-Cheng
, p. 8308 - 8318 (2021/06/28)
A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.
Synthesis of 1,2,3-triazole derivatives of hydnocarpic acid isolated from carpotroche brasiliensis seed oil and evaluation of antiproliferative activity
De Sousa, Bianca L.,Demuner, Antonio J.,Dos Santos, Marcelo H.,Ferraz, Guilherme O.,Ferreira-Silva, Guilherme A.,Ionta, Marisa,Osorio, Liseth S.,Pilau, Eduardo J.,Silva, Evandro,Vareja?, Eduardo V. V.
, p. 2500 - 2510 (2020/11/18)
Carpotroche brasiliensis is a tree native to Brazil, belonging to the family Flacurtiaceae, whose seeds contain a group of cyclopentenyl fatty acids: Gorlic (12%), chaulmugric (27%), and hydnocarpic (48.7%). These compounds are considered the main therapeutic agents in the treatment of leprosy. In the present study, a series of novel triazole compounds were obtained by conjugation between hydnocarpic acid and functionalized azides via copper(I)-catalyzed azidealkyne cycloaddition reaction (CuAAC). Hydnocarpic acid and its derivatives were tested against estrogen-positive breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and non-small cell lung cancer (A549) cell lines. The (R)-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl-11-(cyclopent-2-en-1-yl)undecanoate (8) displayed promising antiproliferative activity against A549 cells. We demonstrated that this compound selectively inhibited the viability of A549 cell cultures. Furthermore, compound 8 inhibited the clonogenic capacity of A549 cells, and this effect was associated to its ability to inhibit cell cycle progression at G1 phase. These findings indicate that 8 is a promising antitumor agent on A549 cells and support further studies to evaluate the molecular mechanisms underlying its antiproliferative activity. In addition, hydnocarpic acid should be considered as a promising chemical prototype to obtain novel antineoplastic agents.
The Method of Producing Aromatic Compound Comprising Pyridin Group
-
Paragraph 0088; 0096-0098, (2020/10/13)
Hydrogen gen storage (Hydrogen Storage) The present invention relates to a method for producing an aromatic compound comprising a pyridine group usable as a Hydrogen Storage (Hydrogen Storage) material for supplying hydrogen to a device using hydrogen, such as a fuel cell and a hydrogen combustion device. More particularly, the present invention relates to a process for preparing an aromatic compound comprising a pyridine group using an oxidation reaction, a halogenation reaction, and Friedel-Craraft (Friririel-Craft) reaction of a pyridine derivative. (by machine translation)
Regioselective Synthesis of 1-Sulfanyl- and 1-Selanylindolizines
Penteado, Filipe,Gomes, Caroline S.,Perin, Gelson,Garcia, Cleisson S.,Bortolatto, Cristiani F.,Brüning, César A.,Lenard?o, Eder J.
, p. 7189 - 7198 (2019/06/14)
We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 °C or 5 min under sonication) and transition-metal-free, using glycerol as a green solvent.
O-H and (CO)N-H bond weakening by coordination to Fe(ii)
Resa, Sandra,Millán, Alba,Fuentes, Noelia,Crovetto, Luis,Luisa Marcos,Lezama, Luis,Choquesillo-Lazarte, Duane,Blanco, Victor,Campa?a, Araceli G.,Cárdenas, Diego J.,Cuerva, Juan M.
supporting information, p. 2179 - 2189 (2019/02/12)
New N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-ethane-1,2-diamine derivatives bearing covalently linked OH and (CO)NH groups have been synthesized. The coordination of those pendant hydroxyl/amide groups to a Fe(ii) metal center is demonstrated both in solution, even in the presence of chloride as the counterion, and in solid state, by means of X-ray diffraction crystal structures. As a result of this coordination, the experimental bond dissociation free energies (BDFE) of O-H and (CO)N-H bonds are remarkably diminished down to 76.0 and 80.5 kcal mol-1 respectively, which is also in agreement with DFT-based theoretical calculations. These BDFE values are in the range of commonly used hydrogen-atom donor reagents. The strategy presented here allows an unequivocal evaluation of the influence of metal coordination in X-H bond weakening in organic solvents which could be easily extended to other metal centers.
Designed To React: Terminal Copper Nitrenes and Their Application in Catalytic C?H Aminations
Moegling, Julian,Hoffmann, Alexander,Thomas, Fabian,Orth, Nicole,Liebh?user, Patricia,Herber, Ulrich,Rampmaier, Robert,Stanek, Julia,Fink, Gerhard,Ivanovi?-Burmazovi?, Ivana,Herres-Pawlis, Sonja
supporting information, p. 9154 - 9159 (2018/07/25)
Heteroscorpionate ligands of the bis(pyrazolyl)methane family have been applied in the stabilisation of terminal copper tosyl nitrenes. These species are highly active intermediates in the copper-catalysed direct C?H amination and nitrene transfer. Novel perfluoroalkyl-pyrazolyl- and pyridinyl-containing ligands were synthesized to coordinate to a reactive copper nitrene centre. Four distinct copper tosyl nitrenes were prepared at low temperatures by the reaction with SO2tBuPhINTs and copper(I) acetonitrile complexes. Their stoichiometric reactivity has been elucidated regarding the imination of phosphines and the aziridination of styrenes. The formation and thermal decay of the copper nitrenes were investigated by UV/Vis spectroscopy of the highly coloured species. Additionally, the compounds were studied by cryo-UHR-ESI mass spectrometry and DFT calculations. In addition, a mild catalytic procedure has been developed where the copper nitrene precursors enable the C?H amination of cyclohexane and toluene and the aziridination of styrenes.
