5048-82-8Relevant academic research and scientific papers
Yeast supported gold nanoparticles: an efficient catalyst for the synthesis of commercially important aryl amines
Krishnan, Saravanan,Patel, Paresh N.,Balasubramanian, Kalpattu K.,Chadha, Anju
supporting information, p. 1915 - 1923 (2021/02/06)
Candida parapsilosisATCC 7330 supported gold nanoparticles (CpGNP), prepared by a simple and green method can selectively reduce nitroarenes and substituted nitroarenes with different functional groups like halides (-F, -Cl, -Br), olefins, esters and nitriles using sodium borohydride. The product aryl amines which are useful for the preparation of pharmaceuticals, polymers and agrochemicals were obtained in good yields (up to >95%) using CpGNP catalyst under mild conditions. The catalyst showed high recyclability (≥10 cycles) and is a robust free flowing powder, stored and used after eight months without any loss in catalytic activity.
Efficient hydrogenation catalyst designing via preferential adsorption sites construction towards active copper
Dai, Xingchao,He, Dongcheng,Li, Teng,Shi, Feng,Wang, Hongli,Wang, Tao,Wang, Xinzhi
, p. 397 - 406 (2021/07/21)
Based on the experimental and DFT calculation results, here for the first time we built preferential adsorption sites for nitroarenes by modification of the supported Cu catalysts surface with 1,10-phenathroline (1,10-phen), by which the yield of aniline via reduction of nitroarene is enhanced three times. Moreover, a macromolecular layer was in-situ generated on supported Cu catalysts to form a stable macromolecule modified supported Cu catalyst, i.e., CuAlOx-M. By applying the CuAlOx-M, a wide variety of nitroarene substrates react smoothly to afford the desired products in up to > 99% yield with > 99% selectivity. The method tolerates a variety of functional groups, including halides, ketone, amide, and C = C bond moieties. The excellent catalytic performance of the CuAlOx-M can be attributed to that the 1,10-phen modification benefits the preferential adsorption of nitrobenzene and slightly weakens adsorption of aniline on the supported nano-Cu surface.
Cobalt nanoclusters coated with N-doped carbon for chemoselective nitroarene hydrogenation and tandem reactions in water
Agostini, Giovanni,Calvino, Jose. J.,Corma, Avelino,Gutiérrez-Tarri?o, Silvia,Lopes, Christian W.,O?a-Burgos, Pascual,Rojas-Buzo, Sergio
supporting information, p. 4490 - 4501 (2021/06/28)
The development of active and selective non-noble metal-based catalysts for the chemoselective reduction of nitro compounds in aquo media under mild conditions is an attractive research area. Herein, the synthesis of subnanometric and stable cobalt nanoclusters, covered by N-doped carbon layers as core-shell (Co@NC-800), for the chemoselective reduction of nitroarenes is reported. TheCo@NC-800catalyst was prepared by the pyrolysis of the Co(tpy)2complex impregnated on Vulcan carbon. In fact, the use of a molecular complex based on six N-Co bonds drives the formation of a well-defined and distributed cobalt core-shell nanocluster covered by N-doped carbon layers. In order to elucidate its nature, it has been fully characterized by using several advanced techniques. In addition, this as-prepared catalyst showed high activity, chemoselectivity and stability toward the reduction of nitro compounds with H2and under mild reaction conditions; water was used as a green solvent, improving the previous results based on cobalt catalysts. Moreover, theCo@NC-800catalyst is also active and selective for the one-pot synthesis of secondary aryl amines and isoindolinones through the reductive amination of nitroarenes. Finally, based on diffraction and spectroscopic studies, metallic cobalt nanoclusters with surface CoNxpatches have been proposed as the active phase in theCo@NC-800material.
A New Nitrogen Pd(II) Complex Immobilized on Magnetic Mesoporous Silica: A Retrievable Catalyst for C–C Bond Formation
Mousavi, Samira,Mansoori, Yagoub,Nuri, Ayat,Koohi-Zargar, Behzad
, p. 1923 - 1936 (2020/11/30)
Abstract: A new nitrogen ligand, i.e. 1,3-di-(o-aminophenoxy)-2-propyl propargyl ether (DPPE), has been synthesized and characterized. Magnetic mesoporous silica composite (MNP@SiO2-SBA) was obtained via embedding magnetite nano-particles (MNPs) between SBA-15 channels. DPPE palladium dichloride (MNP@SiO2-SBA-DPPE-Pd(II)) was then prepared via click chemistry and fully characterized. The activity and recyclability of supported magnetic Pd(II) catalyst were evaluated in Heck coupling reaction after optimizing the optimal reaction conditions including solvent, amount of catalyst, base and temperature. Aryl iodides and aryl bromides showed enhanced activity compared to those of aryl chlorides in the Heck reaction. The catalyst was easily separated magnetically, reused in five runs sequentially, and no significant loss of activity was observed. Graphic Abstract: [Figure not available: see fulltext.]
Commercially Available CuO Catalyzed Hydrogenation of Nitroarenes Using Ammonia Borane as a Hydrogen Source
Du, Jialei,Chen, Jie,Xia, Hehuan,Zhao, Yiwei,Wang, Fang,Liu, Hong,Zhou, Weijia,Wang, Bin
, p. 2426 - 2430 (2020/03/30)
Tandem ammonia borane dehydrogenation and nitroarenes hydrogenation has been reported as a novel strategy for the preparation of aromatic amines. However, the practical application of this strategy is subjected to the high-cost and tedious preparation of supported noble metal nanocatalysts. The commercially available CuO powder is herein demonstrated to be a robust catalyst for hydrogenation of nitroarenes using ammonia borane as a hydrogen source under mild conditions. Numerous amines (even sterically hindered, halogenated, and diamines) could be obtained through this method. This monometallic catalyst is characteristic of support-free, excellent chemoselectivity, low-cost, and high recyclability, which will favor its future utilization in preparative reduction chemistry. Mechanistic studies are also carried out to clarify that diazene and azoxybenzene are key intermediates of this heterogeneous reduction.
A new class of 1,3,5-triazine-based selective estrogen receptor degraders (SERDs): Lead optimization, molecular docking and dynamic simulation
Huang, Ali,Lu, Xiang,Luo, Guoshun,Mao, Jiashun,Sun, Liang,Xiang, Hua,Xiao, Maoxu
, (2020/02/26)
Selective estrogen receptor degrader (SERD) that acts as not only ER antagonist, but also ER degrader, would be useful for the treatment for drug-resistance ER+ breast cancer. However, most of currently available SERD candidates involve very limited molecular scaffolds and are still in clinical trials. In this study, we introduced a 1,3,5-triazine ring into a homobibenzyl motif extracted from amounts of ER ligands and synthesized sixteen SERDs bearing acrylic acid or acrylic amide side chains that possess both ERα antagonism and degradation properties. And all compounds were screened for their anti-proliferative activity against ER+ MCF-7 and Ishikawa cell lines. Among them, compound XHA1614 displayed potent growth inhibition activity against MCF-7 and Ishikawa cells with IC50 values of 3.15 μM and 3.11 μM, respectively. Moreover, XHA1614 could dramatically degrade ER level at 1 nM in a Western blotting assay and afforded an outstanding antagonistic activity via suppressing the expression of progesterone receptor messenger RNA in MCF-7 cells in a RT-PCR assay. Further molecular docking and dynamic simulation on properly selected derivative furnished insights into its binding profile within ERα. Our findings suggest that the 1,3,5-triazine core was a feasible alternative to currently reported SERD scaffold, and provide information that will be useful for further development of promising SERDs candidates for breast cancer therapies.
Superior activity and selectivity of heterogenized cobalt catalysts for hydrogenation of nitroarenes
Li, Wu,Artz, Jens,Broicher, Cornelia,Junge, Kathrin,Hartmann, Heinrich,Besmehn, Astrid,Palkovits, Regina,Beller, Matthias
, p. 157 - 162 (2019/01/10)
The development of improved catalysts for highly selective hydrogenation of nitroarenes is described. For this purpose Co nanoparticles were supported on ordered mesoporous carbon CMK-3 and characterized in detail. The optimal CMK-3-CoPc catalyst exhibits excellent hydrogenation activity for several (hetero)aromatic nitro compounds and yielded the corresponding anilines under mild conditions (40 °C, 20 bar H2).
1,3,5-triazine compound or medicinal salt thereof as well as preparation method and application thereof
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, (2019/10/04)
The invention discloses a 1,3,5-triazine compound of a formula (I) or a formula (II) shown in the specification, or a medicinal salt thereof, and furthermore discloses a preparation method and application of the compound or the medicinal salt thereof. The compound or the medicinal salt thereof disclosed by the invention can be adopted to prepare medicines for treating human breast cancer and endometrial cancer.
Defect-mediated selective hydrogenation of nitroarenes on nanostructured WS2
Sun, Yifan,Darling, Albert J.,Li, Yawei,Fujisawa, Kazunori,Holder, Cameron F.,Liu, He,Janik, Michael J.,Terrones, Mauricio,Schaak, Raymond E.
, p. 10310 - 10317 (2019/11/20)
Transition metal dichalcogenides (TMDs) are well known catalysts as both bulk and nanoscale materials. Two-dimensional (2-D) TMDs, which contain single- and few-layer nanosheets, are increasingly studied as catalytic materials because of their unique thickness-dependent properties and high surface areas. Here, colloidal 2H-WS2 nanostructures are used as a model 2-D TMD system to understand how high catalytic activity and selectivity can be achieved for useful organic transformations. Free-standing, colloidal 2H-WS2 nanostructures containing few-layer nanosheets are shown to catalyze the selective hydrogenation of a broad scope of substituted nitroarenes to their corresponding aniline derivatives in the presence of other reducible functional groups. Microscopic and computational studies reveal the important roles of sulfur vacancy-rich basal planes and tungsten-terminated edges, which are more abundant in nanostructured 2-D materials than in their bulk counterparts, in enabling the functional group selectivity. At tungsten-terminated edges and on regions of the basal planes having high concentrations of sulfur vacancies, vertical adsorption of the nitroarene is favored, thus facilitating hydrogen transfer exclusively to the nitro group due to geometric effects. At lower sulfur vacancy concentrations on the basal planes, parallel adsorption of the nitroarene is favored, and the nitro group is selectively hydrogenated due to a lower kinetic barrier. These mechanistic insights reveal how the various defect structures and configurations on 2-D TMD nanostructures facilitate functional group selectivity through distinct mechanisms that depend upon the adsorption geometry, which may have important implications for the design of new and enhanced 2-D catalytic materials across a potentially broad scope of reactions.
Histone deacetylase inhibitors and its preparation method and use thereof
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Paragraph 0055-0061, (2019/05/15)
The invention discloses a histone deacetylase inhibitor and its preparation method and use, the invention discloses a compound of the formula I as shown, or its crystalline form, or its pharmaceutically acceptable salt, or solvate thereof, or prodrug thereof, or its metabolic product. The invention of the formula I illustrated new compound, has shown good deacetylase inhibition activity, with the histone deacetylase for clinical treatment of diseases associated with abnormal activity of a new pharmaceutical may be.
