- Ammonia borane dehydrogenation and selective hydrogenation of functionalized nitroarene over a porous nickel-cobalt bimetallic catalyst
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The hydrolysis of ammonia borane is a promising strategy for hydrogen energy exploration and exploitation. The in situ produced hydrogen could be directly utilized in hydrogenation reactions. In this work, a bimetallic nickel-cobalt material with porous structure was developed through the pyrolysis of ZIF-67 incorporated with Ni ions. Through the introduction of Ni(NO3)2 as an etching agent, the ZIF-67 polyhedrons were transformed into hollow nanospheres, and further evolved into irregular nanosheets. The bimetallic NiCo phase was formed after pyrolysis in a nitrogen atmosphere at high temperature, with the decomposition and release of organic ligands as gaseous molecules under flowing nitrogen. The obtained bimetallic NiCo porous materials show superior catalytic performance towards hydrolytic dehydrogenation of ammonia borane, thereby nitrobenzene with reducible functional groups can be reduced with high selectivity to the corresponding aniline.
- Miao, Hui,Ma, Kelong,Zhu, Huiru,Yin, Kun,Zhang, Ying,Cui, Yumin
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- Chemoselective hydrogenation of nitroarenes catalyzed by cellulose-supported Pd NPs
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Cellulose-supported palladium nanoparticles (NPs) were prepared by straightforward deposition of metal NPs on modified cellulose. The catalyst exhibited excellent catalytic activity and selectivity in room-temperature hydrogenation of various nitroarenes to arylamines under atmospheric hydrogen pressure in neat water without any additives. High chemoselectivity was also achieved in the hydrogenation of substituted nitroarenes with multiple reducible groups. The catalyst can be recycled by simple centrifugation and reused for at least 4 times without significant decline of yields.
- Li, Dan-dan,Zhang, Jia-wei,Cai, Chun
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- Diruthenium phenylacetylide complexes bearing para -/ meta -amino phenyl substituents
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Presented herein is the synthesis and characterization of four diruthenium(II,III) compounds of formulas Ru2(Xap) 4(C≡C-C6H4-4-NH2) (Xap is 2-anilinopyridinate, 1a; and 2-(3,5-dimethoxy)anilinopyridinate, 1b) and Ru 2(Xap)4(C≡C-C6H4-3-NH 2) (2a/2b). X-ray structural studies of compounds 1b and 2a revealed minimal changes in the coordination sphere of the Ru2 core. Voltammetric measurements showed that compounds 1 exhibit three one-electron redox processes: a reversible reduction of Ru2, a reversible oxidation of Ru2, and a quasi-reversible oxidation of an amino group. Compounds 2 display the same Ru2-based redox processes but not the -NH2 oxidation. Compounds 1a/1b were successfully converted to the corresponding diazonium salts [Ru2(Xap)4-(C≡C-C 6H4-4-N2)](BF4) (3a/3b) via oxidation by nitrosonium tetrafluoroborate, which was generated in situ from t-BuONO and BF3. However, the attempt to convert compounds 2 to the corresponding diazonium salts was unsuccessful. DFT calculations of model compounds were performed to rationalize some unusual structural and electrochemical characteristics observed for compounds 1/2.
- Cummings, Steven P.,Cao, Zhi,Liskey, Carl W.,Geanes, Alex R.,Fanwick, Phillip E.,Hassell, Kerry M.,Ren, Tong
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- Development of a Pre-assembled Through-Bond Energy Transfer (TBET) Fluorescent Probe for Ratiometric Sensing of Anticancer Platinum(ll) Complexes
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Fluorescence microscopy has emerged as an attractive technique to probe the intracellular processing of Pt-based anticancer compounds. Herein, we reported the first through-bond energy transfer (TBET) fluorescent probe NPR1 designed for sensitive detectio
- Ang, Wee Han,Ong, Jun Xiang
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- Selective hydrogenation of nitroarenes to aminoarenes using a MoO:X-modified Ru/SiO2 catalyst under mild conditions
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Modification of Ru/SiO2 with metal oxides (MoOx, WOx, and ReOx) improved the activity and selectivity in the hydrogenation of 3-nitrostyrene to 3-aminostyrene under mild conditions such as 0.3 MPa H2, 303 K, and no solvent. Ru-MoOx/SiO2(Mo/Ru = 1/2) catalyst was applicable to various substituted nitroarenes, providing the corresponding substituted aminoarenes in high yields (85-99%).
- Tamura, Masazumi,Yuasa, Naoto,Nakagawa, Yoshinao,Tomishige, Keiichi
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- A study on the electro-oxidation and electropolymerization of a new OPE linear molecule by EQCM and in situ FTIR spectroelectrochemistry
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A novel symmetric conjugated oligo(phenylene-ethynylene) (OPE) linear molecule (1,4-bis(4-aminophenylethynyl)benzene); BAB) was synthesized by Sonogashira cross-coupling reactions. The structure and purity of the compound were confirmed by 1H N
- Luo, Jiao,Liu, Meiling,Zhao, Qiangqin,Zhao, Jie,Zhang, Youyu,Tan, Liang,Tang, Hao,Xie, Qingji,Li, Haitao,Yao, Shouzhuo
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- Using the hydrogen and oxygen in water directly for hydrogenation reactions and glucose oxidation by photocatalysis
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Direct utilization of the abundant hydrogen and oxygen in water for organic reactions is very attractive and challenging in chemistry. Herein, we report the first work on the utilization of the hydrogen in water for the hydrogenation of various organic compounds to form valuable chemicals and the oxygen for the oxidation of glucose, simultaneously by photocatalysis. It was discovered that various unsaturated compounds could be efficiently hydrogenated with high conversion and selectivity by the hydrogen from water splitting and glucose reforming over Pd/TiO2 under UV irradiation (350 nm). At the same time, glucose was oxidated by the hydroxyl radicals from water splitting and the holes caused by UV irradiation to form biomass-derived chemicals, such as arabinose, erythrose, formic acid, and hydroxyacetic acid. Thus, the hydrogen and oxygen were used ideally. This work presents a new and sustainable strategy for hydrogenation and biomass conversion by using the hydrogen and oxygen in water.
- Zhou, Baowen,Song, Jinliang,Zhou, Huacong,Wu, Tianbin,Han, Buxing
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- Phosphorus-Doped and Lattice-Defective Carbon as Metal-like Catalyst for the Selective Hydrogenation of Nitroarenes
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We report carbon can be activated as metal-like hydrogenation catalyst for the selective hydrogenation of nitroarenes. Using DFT calculations we demonstrated the combination of P dopant and lattice defect in carbon can cause significant electron delocaliz
- Gao, Ruijie,Pan, Lun,Lu, Jinhui,Xu, Jisheng,Zhang, Xiangwen,Wang, Li,Zou, Ji-Jun
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- Cobalt nanoparticles encapsulated in nitrogen-doped carbon for room-temperature selective hydrogenation of nitroarenes
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Here, we report cobalt nanoparticles encapsulated in nitrogen-doped carbon (Co@NC) that exhibit excellent catalytic activity and chemoselectivity for room-temperature hydrogenation of nitroarenes. Co@NC was synthesized by pyrolyzing a mixture of a cobalt
- Gao, Ruijie,Pan, Lun,Li, Zhengwen,Zhang, Xiangwen,Wang, Li,Zou, Ji-Jun
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- One-pot synthesis of monosubstituted aryl(hetaryl)acetylenes by direct introduction of the C≡CH residue into arenes and hetarenes
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A convenient one-pot synthesis of aryl(hetaryl)acetylenes by cross-coupling of aryl(hetaryl)iodides with acetylene in presence of PdCl2(Ph 3)2, CuI and K2CO3 in DMF has been developed.
- Vasilevsky, Sergei F.,Klyatskaya, Svetlana V.,Elguero, José
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- Non-noble metal catalysts for hydrogenation: A facile method for preparing Co nanoparticles covered with thin layered carbon
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Metallic cobalt nanoparticles with surface CoOx patches covered by thin layered carbon (named Co@C) have been directly synthesized by thermal decomposition of Co-EDTA complex. Raman spectra and HRTEM images suggest that discontinuities can be found in the disordered layered carbon. XPS shows that the CoOx patches in the Co@C nanoparticles can reduced to metallic Co by H2 under reaction conditions (7 bar at 120 °C), and H2-D2 exchange experiments show that the reduced metallic Co nanoparticles covered by carbon layers can dissociate H2. The Co@C nanoparticles show excellent activity and selectivity during chemoselective hydrogenation of nitroarenes for a wide scope of substrates under mild reaction conditions. Based on the results from DRIFTS adsorption experiments, we propose that metallic Co in the Co@C nanoparticles is the active phase. The role of the carbon layers is to protect the Co from overoxidation by air, leading to the chemoselective hydrogenation of nitroarenes.
- Liu, Lichen,Concepción, Patricia,Corma, Avelino
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- Bulk iron pyrite as a catalyst for the selective hydrogenation of nitroarenes
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Bulk iron pyrite (FeS2) functions as an inexpensive, Earth-abundant, off-the-shelf catalyst capable of selectively hydrogenating a broad scope of substituted nitroarenes to their corresponding aniline derivatives using molecular hydrogen.
- Morse, James R.,Callejas, Juan F.,Darling, Albert J.,Schaak, Raymond E.
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- Synthesis and asymmetric catalytic performance of one-handed helical poly(phenylacetylene)s bearing proline dipeptide pendants
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One-handed helical substituted polyacetylene has received extensive attention due to its potential in chiral stationary phases and molecular recognition. Here, three one-handed helical poly(phenylacetylene)s bearing proline or proline dipeptide as the pen
- Liu, Lijia,Wang, Yaodong,Wang, Fuqingyun,Zhang, Chunhong,Zhou, Yanli,Zhou, Zhengjin,Liu, Xudong,Zhu, Ruiqi,Dong, Hongxing,Satoh, Toshifumi
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- Boosting chemoselective reduction of 4-nitrostyreneviaphotoinduced energetic electrons fromin situformed Cu nanoparticles on carbon dots
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Chemoselective hydrogenation of structurally diverse nitroarenes is a challenging process that often requires precious metal catalysts and proceeds in an organic solvent. Herein, a convenient and stable hybrid nanocatalyst combining carbon dots and copper nanoparticles is developed as an ideal alternative for this transformation. The as-prepared nanocatalyst achieves over 99% selectivity for the formation of 4-aminostyrene at 100% conversion of 4-nitrostyrene in an aqueous solvent under visible light irradiation. Compared with other reported catalysts, our presented catalyst shows more superior hydrogenation selectivity and stability as well as lower material cost. This high efficiency could be originated from the nanocatalyst's ability to synergistically control surface hydrogen species released from ammonia borane and energetic “hot” electrons induced by visible light irradiation for the selective reduction reaction. Compared with other reported catalysts, our presented nanocatalyst is better for the realization of energy-saving chemical processes by introducing solar energy.
- Ren, Yuqi,Hao, Caihong,Chang, Qing,Li, Ning,Yang, Jinlong,Hu, Shengliang
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- High Catalytic Activity and Chemoselectivity of Sub-nanometric Pd Clusters on Porous Nanorods of CeO2 for Hydrogenation of Nitroarenes
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Sub-nanometric Pd clusters on porous nanorods of CeO2 (PN-CeO2) with a high Pd dispersion of 73.6% exhibit the highest catalytic activity and best chemoselectivity for hydrogenation of nitroarenes to date. For hydrogenation of 4-nitr
- Zhang, Sai,Chang, Chun-Ran,Huang, Zheng-Qing,Li, Jing,Wu, Zhemin,Ma, Yuanyuan,Zhang, Zhiyun,Wang, Yong,Qu, Yongquan
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- Molecular design directs self-assembly of DPP polycatenars into 2D and 3D complex nanostructures
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Novel diketopyrrolopyrrole (DPP) based polycatenars characterized with a long π-conjugated rigid calamitic core, different side groups (t-Boc, H or PEO) at the lactam N atoms of the central DPP core and terminal hydrophobic paraffinic chains were prepared
- Chang, Qing,Cheng, Xiaohong,Du, Xuyang,Ge, Tao,Liu, Xinhao,Ma, Tao
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- Industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles-catalyzed hydrogenation of nitroarenes
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The development of green and efficient methods for hydrogenation of nitroarenes is still highly demanding in organic synthesis. Herein, we report an industrial Cunninghamia lanceolata carbon supported FeO(OH) nanoparticles process for the synthesis of aryl amines with good yields via hydrogenation of nitroarenes. Nine key anti-cancer drug intermediates were successfully achieved with protocol. And Osimertinib intermediate 4m can be smoothly synthesized at a 2.67 kg-scale with >99.5% HPLC purity. This protocol features cheap carbon source, highly catalytic activity, simple operation, kilogram-scalable and recyclable catalysts (eight times without observable losing activity).
- Fu, Lihua,Li, Dingzhong,Lu, Hao,Qiu, Renhua,Sun, Tulai,Xing, Chen,Yang, Tianbao
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- Preparation method of acetenyl aniline
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The invention discloses a preparation method of acetenyl aniline, wherein the preparation method comprises the following steps: by using nitroethylbenzene as a raw material and MBr-MBrO3-H2SO4 (M=Na or K) as a bromination reagent, carrying out free radical bromination reaction to prepare 1,1-dibromo-1-(nitrophenyl)ethane, carrying out elimination reaction under the action of alkali to obtain nitrophenylacetylene, and finally, carrying out Fe/HCl reduction to obtain acetenyl aniline. The preparation method provided by the invention has the advantages of cheap and easily available raw materials, simple and safe operation, good reaction selectivity, high product yield, less emission of three wastes and the like.
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- Sustainable and recyclable palladium nanoparticles–catalyzed reduction of nitroaromatics in water/glycerol at room temperature
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Palladium nanoparticles with unique catalytic activity and high stability are synthesized. These nanoparticles exhibit excellent catalytic reduction activity for nitroaromatics in green solvents in the presence of H2 at ambient pressure and temperature. The prominent advantages of this nanotechnology include low consumption of catalyst, excellent chemoselectivity, high reusability of the catalyst, and environmentally green solvents.
- Chen, Jin,Dai, Bencai,Liu, Changchun,Shen, Zhihao,Zhao, Yongde,Zhou, Yang
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p. 540 - 544
(2020/07/14)
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- 1,3-Diphenyldisiloxane Enables Additive-Free Redox Recycling Reactions and Catalysis with Triphenylphosphine
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The recently reported chemoselective reduction of phosphine oxides with 1,3-diphenyldisiloxane (DPDS) has opened up the possibility of additive-free phosphine oxide reductions in catalytic systems. Herein we disclose the use of this new reducing agent as an enabler of phosphorus redox recycling in Wittig, Staudinger, and alcohol substitution reactions. DPDS was successfully utilized in ambient-temperature additive-free redox recycling variants of the Wittig olefination, Appel halogenation, and Staudinger reduction. Triphenylphosphine-promoted catalytic recycling reactions were also facilitated by DPDS. Additive-free triphenylphosphine-promoted catalytic Staudinger reductions could even be performed at ambient temperature due to the rapid nature of phosphinimine reduction, for which we characterized kinetic and thermodynamic parameters. These results demonstrate the utility of DPDS as an excellent reducing agent for the development of phosphorus redox recycling reactions.
- Buonomo, Joseph A.,Cole, Malcolm S.,Eiden, Carter G.,Aldrich, Courtney C.
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p. 3583 - 3594
(2020/09/15)
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- On-Demand, Ultraselective Hydrogenation System Enabled by Precisely Modulated Pd-Cd Nanocubes
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The pursuit of efficient hydrogenation nanocatalysts with a desirable selectivity toward intricate substrates is state-of-the-art research but remains a formidable challenge. Herein, we report a series of novel PdCdx nanocubes (NCs) for ultraselective hydrogenation reactions with flexible tuning features. Obtaining a desirable conversion level of the substrates (e.g., 4-nitrophenylacetylene (NPA), 4-nitrobenzaldehyde (NBAD), and 4-nitrostyrene (NS)) and competitive selectivity for all potential hydrogenation products have been achieved one by one under optimized hydrogenation conditions. The performance of these PdCdx NCs displays an evident dependence on both the composition and the use of Cd and a need for a distinct hydrogen source (H2 or HCOONH4). Additionally, for the selectivity of hydrogen to be suitably high, the morphology of the NCs has a very well-defined effect. Density functional theory calculations confirmed the variation of adsorption energy for the substrate and hydrogenation products by carefully controlled introduction of Cd, leading to a desirable level of selectivity for all potential hydrogenation products. The PdCdx NCs also exhibit excellent reusability with negligible activity/selectivity decay and structural/composition changes after consecutive reactions. The present study provides an advanced strategy for the rational design of superior hydrogenation nanocatalysts to achieve a practical application for desirable and selective hydrogenation reaction efficiency.
- Feng, Yonggang,Xu, Weiwei,Huang, Bolong,Shao, Qi,Xu, Lai,Yang, Shize,Huang, Xiaoqing
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supporting information
p. 962 - 972
(2020/02/20)
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- Catalytic hydrogenation reduction method of aromatic nitro compound
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The invention discloses a method for catalytic hydrogenation reduction of an aromatic nitro compound. The method comprises the following steps: feeding an aromatic nitro compound, a solvent and a catalyst into an autoclave, and carrying out a hydrogenation reduction reaction under the condition of filling the autoclave with hydrogen to obtain a corresponding aromatic amino compound product. The conversion rate of the aromatic nitro compound and the selectivity of the product can be up to 99% or above; the catalyst is a carbon-loaded nitrogen-doped cobalt nano material (catalyst Co-N/C for short) or a carbon-loaded nitrogen-doped iron nano material (a catalyst Fe-N/C for short). The catalytic hydrogenation method provided by the invention has the characteristics of high catalytic activity,high selectivity of the target product, good universality of the aromatic nitro compound substrate, easy separation and recovery of the catalyst and the like, and has a good industrial application prospect.
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Paragraph 0016; 0022
(2020/06/02)
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- Design, synthesis, and structure-activity relationship of 7-propanamide benzoxaboroles as potent anticancer agents
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Benzoxaboroles, as a novel class of bioactive molecules with unique physicochemical properties, have been shown to possess excellent antimicrobial activities with tavaborole approved in 2014 as an antifungal drug. Although urgently needed, the investigation of benzoxaboroles as anticancer agents has been lacking so far. In this study, we report the design, synthesis, and anticancer structure-activity relationship of a series of 7-propanamide benzoxaboroles. Compounds 103 and 115 showed potent activity against ovarian cancer cells with IC50 values of 33 and 21 nM, respectively. Apoptosis was induced by these compounds and colony formation was effectively inhibited. Furthermore, they also showed excellent efficacy in ovarian tumor xenograft mouse model.
- Zhang, Jiong,Zhang, Jinyi,Hao, Guiyun,Xin, Weixiang,Yang, Fei,Zhu, Mingyan,Zhou, Huchen
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p. 6765 - 6784
(2019/08/20)
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- Design, synthesis and biological evaluation of novel uracil derivatives bearing 1, 2, 3-triazole moiety as thymidylate synthase (TS) inhibitors and as potential antitumor drugs
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Research on thymidylate synthase inhibitors has been a hot spot for anticancer drug development. Here, based on the structures and pharmacological properties of two types of TS inhibitors, through a molecular assembly principle of drugs design, we designed and synthesized a series of 30 novel uracil derivatives as TS inhibitors. The antiproliferative ability of these compounds was evaluated against four cancer cell lines (A549, OVCAR-3, SGC-7901, and HepG2) by the MTT assay. Most of them showed excellent activities against all the tested cell lines. Furthermore, hTS assay results showed that these compounds have the unique ability to inhibit hTS activity in vitro. Notably, compound 13j exhibited the most potent activity against A549 cells (IC50 = 1.18 μM) and extremely prominent enzyme inhibition (IC50 = 0.13 μM), which was superior to the pemetrexed (PTX, IC50 = 3.29 μM and IC50 = 2.04 μM). Flow cytometric analysis showed the compound 13j could inhibit A549 cells proliferation by arresting the cell cycle in the G1/S phase, then induced the cell apoptosis. Further western blot analysis showed that compound 13j could down-regulate the cycle checkpoint proteins cyclin D1 and cyclin E to inhibit the cell cycle progression, and then induce intrinsic apoptosis by activating caspase-3, and reducing the ratio of bcl-2/bax. All of these results demonstrated that this new structure has potential drug-making properties and provides new ideas for drug development.
- Lu, Guo-qing,Li, Xin-yang,Mohamed O, Kamara,Wang, Depu,Meng, Fan-hao
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p. 282 - 296
(2019/03/27)
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- Cobalt Entrapped in N,S-Codoped Porous Carbon: Catalysts for Transfer Hydrogenation with Formic Acid
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Catalysts with Co nanoparticles (NPs) entrapped in N,S-codoped carbon shells were successfully fabricated by pyrolysis of porous organic polymers (POPs) with cobalt salts. The encapsulated structure consisting of Co NPs and N,S-codoped carbon layers was verified by TEM, XRD, and X-ray photoelectron spectroscopy. The catalysts displayed excellent activity and stability for the catalytic transfer hydrogenation (CTH) of nitrobenzene with formic acid under base-free conditions. Furthermore, the resultant catalysts allowed for highly efficient and selective transfer hydrogenation of various functionalized nitroarenes to the corresponding anilines. Through control experiments, the covered Co NPs were identified as active sites for CTH. The incorporation of S into the N-doped carbon lattice promoted the electron transfer from metallic cobalt NPs to their shells, which played a significant role in the acceleration of CTH. Moreover, the Co-NSPC-850 catalyst pyrolyzed at 850 °C showed excellent stability in the recycling experiments.
- Guo, Haotian,Gao, Ruixiao,Sun, Mingming,Guo, Hao,Wang, Bowei,Chen, Ligong
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p. 487 - 494
(2019/01/24)
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- Fe/Fe3C Encapsulated in N-Doped Carbon Tubes: A Recyclable Catalyst for Hydrogenation with High Selectivity
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Herein, a series of Fe-based catalysts have been designed and prepared by grinding a mixture of MIL-88d and melamine, and then the mixture was followed by pyrolysis. An unusual Fe/Fe3C-activated site is uniformly encapsulated in the N-doped carbon tubes obtained by pyrolysis of the film-like nanocrystals of MIL-88d. Experimental characterizations and theoretical calculations demonstrate that the surface N sites can effectively trap the nitrobenzene and aniline by their phenyl groups with the formation of three C-N bonds that made the catalyst exhibit excellent catalytic activity (turnover frequencies of ≤11268 h-1 calculated on the basis of nitrobenzene) and chemoselectivity for the reduction of nitro derivatives under facile conditions.
- Yun, Ruirui,Zhang, Shi,Ma, Wanjiao,Lv, Xiao,Liu, Shoujie,Sheng, Tian,Wang, Suna
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supporting information
p. 9469 - 9475
(2019/08/20)
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- Visible light-driven selective hydrogenation of unsaturated aromatics in an aqueous solution by direct photocatalysis of Au nanoparticles
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Selective hydrogenation of various chemical bonds, such as CC, CC, CO, NO, and CN, is efficiently driven by visible light over a supported gold nanoparticle (AuNP) photocatalyst under mild reaction conditions. The reaction system exhibits high substituent tolerance and tunable selectivity by light wavelength. Density functional theory (DFT) calculations demonstrated a strong chemisorption between the reactant molecule and metal resulting in hybridized orbitals. It is proposed that direct photoexcitation between hybridized orbitals is the main driving force of the hydrogenation reaction. The hydrogenation pathway is investigated by the isotope tracking technique. We revealed the cooperation of water and formic acid (FA) as a hydrogen source and the hydrogenation route through Au-H species on the AuNP surface.
- Huang, Yiming,Liu, Zhe,Gao, Guoping,Xiao, Qi,Martens, Wayde,Du, Aijun,Sarina, Sarina,Guo, Cheng,Zhu, Huaiyong
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p. 726 - 734
(2018/02/14)
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- Heterogeneous Iron-Catalyzed Hydrogenation of Nitroarenes under Water-Gas Shift Reaction Conditions
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Reduction of various nitroarenes in the presence of heterogeneous iron oxide-based catalyst Fe 2 O 3 /NGr@C under water-gas shift reaction (WGSR) conditions has been demonstrated. The catalytic material is prepared in a straightforward manner via deposition/pyrolysis of iron-phenanthroline complex on carbon support. It shows high chemoselectivity towards the reduction of nitroarenes in the presence of other reducible and/or poisoning-capable functional groups. Hydrogenation is achieved using CO/H 2 O as a hydrogen source. Furthermore, it is demonstrated that the presence of triethylamine additive has a significant positive effect on the rate of reduction.
- Ryabchuk, Pavel,Junge, Kathrin,Beller, Matthias
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supporting information
p. 4369 - 4376
(2018/11/21)
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- Synthesis of N-aryl and N-heteroaryl hydroxylamines via partial reduction of nitroarenes with soluble nanoparticle catalysts
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Polystyrene-supported ruthenium nanoparticles enable the selective hydrazine-mediated reduction of nitroarenes to hydroxylamine products in high yield and selectivity. Key to obtaining the hydroxylamine product in good yield was the use of organic solvents capable of solubilizing the polystyrene-supported nanoparticle catalyst. N-aryl and N-heteroaryl hydroxylamines are generated under exceptionally mild conditions and in the presence of a various easily reduced functional groups.
- Tyler, Jefferson H.,Nazari, S. Hadi,Patterson, Robert H.,Udumula, Venkatareddy,Smith, Stacey J.,Michaelis, David J.
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supporting information
p. 82 - 86
(2016/12/23)
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- Self-recognition behavior of novel frameworks containing both urea and carboxylate anion motifs
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Molecular recognition based on hydrogen bond interaction plays a significant role in supramolecular self-assembly. In this work, we successfully developed a class of novel frameworks containing a urea in the recognition site and a carboxylate anion in the
- Xu, Zhiqiang,Ge, Haojie,Han, Xie,Liu, Sheng Hua,Meng, Xiang-Gao,Yin, Jun
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p. 6386 - 6391
(2017/10/06)
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- Catalytic Materials Based on Surface Coating with Poly(ethyleneimine)-Stabilized Gold Nanoparticles
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Gold nanoparticles (AuNPs) can be obtained from HAuCl4 by using poly(ethyleneimine) (PEI) as both reductant and stabilizing agent. However, the known affinity of PEI for different materials has not been exploited to coat them and turn their surface catalytic. We demonstrate that the irradiation of a solution of HAuCl4 and branched PEI 1800 (bPEI2K) with microwave (MW) yields PEI-stabilized AuNPs (MW-PEI@AuNPs) with an average size of 7.6 nm that are catalytically active in the reduction with NaBH4 of different nitroarenes functionalized with a variety of functional groups. Moreover, the as-prepared MW-PE@-AuNPs show affinity for different materials such as polystyrene (standard spectrophotometry disposal cuvettes), polypropylene (Falcon-type tubes), and silica (Silica gel 60), turning their surface catalytic without any additional synthetic step. This feature was exploited to transform standard tubing (Tygon, poly(ether ether ketone), and stainless steel) into flow reactors by simple passage of a solution of MW-PEI@AuNPs. This straightforward functionalization is especially appealing in the case of the stainless-steel tubing, one of the materials more widely used in HPLC, which is of interest for flow nanocatalysis.
- Ortega-Mu?oz, Mariano,Blanco, Victor,Hernandez-Mateo, Fernando,Lopez-Jaramillo, F. Javier,Santoyo-Gonzalez, Francisco
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p. 3965 - 3973
(2017/09/14)
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- Silver and palladium alloy nanoparticle catalysts: Reductive coupling of nitrobenzene through light irradiation
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Silver-palladium (Ag-Pd) alloy nanoparticles strongly absorb visible light and exhibit significantly higher photocatalytic activity compared to both pure palladium (Pd) and silver (Ag) nanoparticles. Photocatalysts of Ag-Pd alloy nanoparticles on ZrO2 and Al2O3 supports are developed to catalyze the nitroaromatic coupling to the corresponding azo compounds under visible light irradiation. Ag-Pd alloy NP/ZrO2 exhibited the highest photocatalytic activity for nitrobenzene coupling to azobenzene (yield of ~80% in 3 hours). The photocatalytic efficiency could be optimized by altering the Ag:Pd ratio of the alloy nanoparticles, irradiation light intensity, temperature and wavelength. The rate of the reaction depends on the population and energy of the excited electrons, which can be improved by increasing the light intensity or by using a shorter wavelength. The knowledge developed in this study may inspire further studies on Ag alloy photocatalysts and organic syntheses using Ag-Pd nanoparticle catalysts driven under visible light Irradiation.
- Peiris, Sunari,Sarina, Sarina,Han, Chenhui,Xiao, Qi,Zhu, Huai-Yong
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p. 10665 - 10672
(2017/08/21)
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- Method for preparing aminophenylacetylene through nitrobenzene acetylene hydrogenation
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The invention relates to a method for preparing aminophenylacetylene through nitrobenzene acetylene hydrogenation. The method comprises the following steps: in a green solvent absolute ethyl alcohol, by taking Pt-Zn/SnO2-Sb2O3 as a catalyst, catalyzing ni
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Paragraph 0014
(2017/10/22)
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- Co-based heterogeneous catalysts from well-defined Α-diimine complexes: Discussing the role of nitrogen
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Ar-BIANs and related α-diimine Co complexes were wet impregnated onto Vulcan XC 72 R carbon black powder and used as precursors for the synthesis of heterogeneous supported nanoscale catalysts by pyrolysis under argon at 800?°C. The catalytic materials feature a core-shell structure composed of metallic Co and Co oxides decorated with nitrogen-doped graphitic layers (NGr). These catalysts display high activity in the liquid phase hydrogenation of aromatic nitro compounds (110?°C, 50 bar H2) to give chemoselectively substituted aryl amines. The catalytic activity is closely related to the amount and type of nitrogen atoms in the final catalytic material, which suggests a heterolytic activation of dihydrogen.
- Formenti, Dario,Ferretti, Francesco,Topf, Christoph,Surkus, Annette-Enrica,Pohl, Marga-Martina,Radnik, J?rg,Schneider, Matthias,Junge, Kathrin,Beller, Matthias,Ragaini, Fabio
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- The design of liquid crystalline bistolane-based materials with extremely high birefringence
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We designed three new bistolanes with alkylsulfanyl groups. A symmetric derivative contains short terminal methylsulfanyl groups (-SCH3) on both ends, while two asymmetric derivatives contain a methylsulfanyl group on one end, as well as a highly polarizable cyano (-CN) or isothiocyanate (-NCS) group on the other end. These materials exhibited a well-defined enantiotropic nematic phase, as well as an extremely high birefringence (Δn > 0.6). Most notably, the NCS derivative achieves an extremely high value of 0.77 at 550 nm. These results should be helpful for the design and synthesis of novel nematic materials with high birefringence.
- Arakawa, Yuki,Kang, Sungmin,Tsuji, Hideto,Watanabe, Junji,Konishi, Gen-Ichi
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p. 92845 - 92851
(2016/10/11)
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- Pyrimidine or pyridine pyridine ketone compound and its preparation method and application (by machine translation)
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The invention discloses a kind of type I of the pyrimidine or pyridine pyridine ketone compound and its preparation and application, which belongs to the technical field of pharmaceutical preparation. The compounds have high-efficient and selectively inhibit the cell cycle dependent kinases (Cdks) CDK4 and CDK6 active, and then by inhibiting CDK4/CDK6 prevent tumor cell division. Therefore, the compounds of this invention can be used for CDK4 and CDK6 the involved in cell cycle control disorders result in various diseases, especially suitable for the treatment of malignant tumors. (by machine translation)
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Paragraph 0282
(2016/10/09)
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- Recyclable and Selective Nitroarene Hydrogenation Catalysts Based on Carbon-Coated Cobalt Oxide Nanoparticles
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Co/CoO nanoparticles coated with graphene layers (Co/CoO@Carbon) have been developed through direct heating treatment of cobalt oxide precursors incipiently deposited over nanographite materials. Cobalt oxides are partially reduced to active zero-valent metal species and the simultaneous formation of carbon layers over the nanoparticles protects them from oxidation and deactivation. This nanocatalyst performs excellently in chemoselective hydrogenation of some challenging nitroarenes with reducible functionalities to the corresponding anilines. The catalyst is kept in active and selective performance in a ten-run recycling test.
- Chen, Bingfeng,Li, Fengbo,Huang, Zhijun,Yuan, Guoqing
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p. 1132 - 1138
(2016/04/05)
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- Chemoselective transfer hydrogenation of nitroarenes by highly dispersed Ni-Co BMNPs
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Highly dispread Ni-Co bimetallic nanoparticles (Ni-Co BMNPs) are synthesized and applied as an efficient catalyst in the chemoselective transfer hydrogenation of nitroarenes (CTH) using hydrazine hydrate as the hydrogen donor. The BMNPs can efficiently catalyze the reduction reaction without any additives under mild conditions with high TOF. Significantly higher activity is achieved when compared with corresponding single-component catalysts, optimal composition of the Ni-Co BMNPs was screened which was proved to be crucial in both the selectivity and yields. Excellent performance of Ni-Co BMNPs can be ascribed to the improved dispersion of active sites on the BMNPs surface (compared with Ni NPs) and the electron transfer from cobalt to nickel.
- Zhang, Jia-Wei,Lu, Guo-Ping,Cai, Chun
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- Metal-Free Reduction of Aromatic Nitro Compounds to Aromatic Amines with B2pin2 in Isopropanol
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A metal-free reduction of aromatic nitro compounds to the corresponding amines has been achieved by a combination of B2pin2 and KOtBu in isopropanol. A series of nitro compounds containing various reducible functional groups were chemoselectively reduced in good to excellent yields.
- Lu, Hongtao,Geng, Zhiyue,Li, Jingya,Zou, Dapeng,Wu, Yusheng,Wu, Yangjie
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supporting information
p. 2774 - 2776
(2016/06/15)
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- Synthesis of Nickel Nanoparticles with N-Doped Graphene Shells for Catalytic Reduction Reactions
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The synthesis of novel nanoparticles is of general importance for the development of efficient heterogeneous catalysts. Herein, the preparation of carbon-supported nickel-based nanoparticles (NPs), modified by nitrogen-doped graphene layers, is reported for the first time. The resulting materials were characterized in detail by TEM, X-ray photoelectron spectroscopy (XPS), XRD, elemental analysis (EA), electron paramagnetic resonance (EPR), temperature-programmed reduction (TPR), BET, and Raman analysis. Initial catalytic tests revealed the potential of this class of compounds in hydrogenation reactions.
- Pisiewicz, Sabine,Formenti, Dario,Surkus, Annette-Enrica,Pohl, Marga-Martina,Radnik, J?rg,Junge, Kathrin,Topf, Christoph,Bachmann, Stephan,Scalone, Michelangelo,Beller, Matthias
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p. 129 - 134
(2016/01/25)
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- Chemoselective hydrogenation of functionalized nitroarenes using MOF-derived co-based catalysts
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The synthesis, characterization, and application of nitrogen-doped carbon supported Co catalysts in selective hydrogenation of nitroarenes are described. The cobalt-based catalysts are prepared by simple pyrolysis of ZIF-67, a typical MOF material, under inert atmosphere. Physicochemical properties of the Co/C-N catalysts have been investigated by X-ray diffraction, elemental analysis, atomic absorption spectroscopy, scanning electron microscopy, transmission electron microscopy, Fourier transform infrared spectroscopy, and X-ray photoelectron spectroscopy. The Co-based materials were found to be highly efficient in the chemoselective hydrogenation of nitroarenes. A broad range of substituted nitroarenes are converted to the corresponding anilines in excellent yields under industrially viable conditions with other reducing groups remaining intact. In situ ATR-IR and XPS characterizations reveal that the Co-N centers present in the catalyst favor the preferential adsorption of nitro groups, leading to this unique chemoselectivity. The kinetic parameters of 4-nitrostyrene hydrogenation over the Co/C-N catalyst were investigated.
- Wang, Xi,Li, Yingwei
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- Alloying Gold with Copper Makes for a Highly Selective Visible-Light Photocatalyst for the Reduction of Nitroaromatics to Anilines
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Finely control of product selectivity is an essential issue in organic chemical production. In the synthesis of functionalized anilines via reduction of the corresponding nitroarenes, the challenge is to selectively reduce only the nitro group in the presence of other reducible functional groups in nitroarene molecules at a high reaction rate. Normally, the nitroarene is reduced stepwise through a series of intermediates that remain as byproducts, increasing the aniline synthesis cost. Here we report that alloying small amounts of copper into gold nanoparticles can alter the reaction pathway of the catalytic reduction under visible-light irradiation at ambient temperature, allowing nitroaromatics to be transformed directly to anilines in a highly selective manner. The reasons for the high efficiency of the photocatalytic reduction under these comparatively benign conditions as well as the light-excited reaction mechanisms are discussed. This photocatalytic process avoids byproducts, exhibits a high reaction rate and excellent substituent tolerance, and can be used for the synthesis of many useful functionalized anilines under environmentally benign conditions. Switching of the reaction pathway simply by tailoring the bimetallic alloy NPs of the photocatalysts is effective for engineering of product chemoselectivity.
- Xiao, Qi,Sarina, Sarina,Waclawik, Eric R.,Jia, Jianfeng,Chang, Jin,Riches, James D.,Wu, Haishun,Zheng, Zhanfeng,Zhu, Huaiyong
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p. 1744 - 1753
(2016/03/15)
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- Structure-based design, synthesis and evaluation in vitro of arylnaphthyridinones, arylpyridopyrimidinones and their tetrahydro derivatives as inhibitors of the tankyrases
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Abstract The tankyrases are members of the PARP superfamily; they poly(ADP-ribosyl)ate their target proteins using NAD+ as a source of electrophilic ADP-ribosyl units. The three principal protein substrates of the tankyrases (TRF1, NuMA and axin) are involved in replication of cancer cells; thus inhibitors of the tankyrases may have anticancer activity. Using structure-based drug design and by analogy with known 3-arylisoquinolin-1-one and 2-arylquinazolin-4-one inhibitors, series of arylnaphthyridinones, arylpyridinopyrimidinones and their tetrahydro-derivatives were synthesised and evaluated in vitro. 7-Aryl-1,6-naphthyridin-5-ones, 3-aryl-2,6-naphthyridin-1-ones and 3-aryl-2,7-naphthyridin-1-ones were prepared by acid-catalysed cyclisation of the corresponding arylethynylpyridinenitriles or reaction of bromopyridinecarboxylic acids with β-diketones, followed by treatment with NH3. The 7-aryl-1,6-naphthyridin-5-ones were methylated at 1-N and reduced to 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones. Cu-catalysed reaction of benzamidines with bromopyridinecarboxylic acids furnished 2-arylpyrido[2,3-d]pyrimidin-4-ones. Condensation of benzamidines with methyl 1-benzyl-4-oxopiperidine-3-carboxylate and deprotection gave 2-aryl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidin-4-ones, aza analogues of the known inhibitor XAV939. Introduction of the ring-N in the arylnaphthyridinones and the arylpyridopyrimidinones caused >1000-fold loss in activity, compared with their carbocyclic isoquinolinone and quinazolinone analogues. However, the 7-aryl-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-ones showed excellent inhibition of the tankyrases, with some examples having IC50 = 2 nM. One compound (7-(4-bromophenyl)-1-methyl-1,2,3,4-tetrahydro-1,6-naphthyridin-5-one) showed 70-fold selectivity for inhibition of tankyrase-2 versus tankyrase-1. The mode of binding was explored through crystal structures of inhibitors in complex with tankyrase-2.
- Kumpan, Katerina,Nathubhai, Amit,Zhang, Chenlu,Wood, Pauline J.,Lloyd, Matthew D.,Thompson, Andrew S.,Haikarainen, Teemu,Lehti?, Lari,Threadgill, Michael D.
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supporting information
p. 3013 - 3032
(2015/08/03)
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- Tunable electron acceptors based on cyclopenta[hi]aceanthrylenes
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A series of substituted cyclopenta[hi]aceanthrylene derivatives with electron donating (NH2, OCH3), neutral (H), and electron withdrawing (COOH, CF3, CN, NO2) substituents were prepared. A room-temperature Sonogashira cross-coupling reaction between 2,7-dibromocyclopenta[hi]aceanthrylene and an appropriately functionalized phenylene ethynylene precursor was utilized to access the materials that were characterized by Nuclear Magnetic Resonance Spectroscopy (NMR), cyclic voltammetry (CV), and UV-Vis spectroscopy. The highest occupied molecular orbital (HOMO) and lowest unoccupied molecular orbital (LUMO) were systematically varied when proceeding from electron donating to electron withdrawing substituents. The optical band gap was significantly altered for the most electron donating species, while little change was observed between different electron withdrawing substituents. This study demonstrates the ability to control the frontier orbital energies of this class of cyclopenta-fused polycyclic aromatic hydrocarbon materials through selective substitution.
- Zhu, Xinju,Yuan, Bingxin,Plunkett, Kyle N.
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supporting information
p. 7105 - 7107
(2015/12/01)
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- Dual optimization approach to bimetallic nanoparticle catalysis: Impact of M1/M2 ratio and supporting polymer structure on reactivity
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A dual optimization approach to nanoparticle catalysis is reported in which both the composition of a bimetallic nanoparticle and the electronic properties of the supporting polystyrene-based polymer can be varied to optimize reactivity and chemoselectivity in nitroarene reductions. Ruthenium-cobalt nanoparticles supported on polystyrene are shown to catalyze nitroarene reductions at room temperature with exceptional activity, as compared with monometallic ruthenium catalysts. Both the identity of the second metal and the M1/M2 ratio show a profound effect on the chemoselectivity of nitroarene reductions. These polymer-supported bimetallic catalysts are shown to react with nearly complete chemoselectivity for nitro group reduction over a variety of easily reducible functional groups. The electronic properties of the supporting polymer also have a significant impact on catalysis, in which electron-deficient polystyrenes enable 100% conversion to the aniline product in just 20 min at room temperature. Polymer effects are also shown to influence the mechanism of the reduction reaction, in addition to accelerating the rate, confirming the impact of the polymer structure on catalytic efficiency. These catalysts are easily prepared in a single step from commercial materials and can be readily recycled without loss of activity.
- Udumula, Venkatareddy,Tyler, Jefferson H.,Davis, Donald A.,Wang, Hao,Linford, Matthew R.,Minson, Paul S.,Michaelis, David J.
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p. 3457 - 3462
(2015/06/16)
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- Selective conversion of nitroarenes using a carbon nanotube-ruthenium nanohybrid
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Ruthenium nanoparticles were assembled on carbon nanotubes and the resulting nanohybrid was used in the hydrazine-mediated catalytic hydrogenation of various nitroarenes, at room temperature. Depending on the solvent, a selective transformation occurred, giving either access to the corresponding aniline or hydroxylamine derivative.
- Jawale, Dhanaji V.,Gravel, Edmond,Boudet, Caroline,Shah, Nimesh,Geertsen, Valérie,Li, Haiyan,Namboothiri, Irishi N. N.,Doris, Eric
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supporting information
p. 1739 - 1742
(2015/03/03)
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- Reduction of nitroarenes using CO and H2O in the presence of a nanostructured cobalt oxide/Nitrogen-Doped Graphene (NGr) catalyst
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The most common route to anilines is based on the reduction of the corresponding nitroarenes. In general, hydrogen is preferred as reducing agent and numerous catalytic systems are known to achieve such transformations. Besides, the use of CO/H2O as hydrogen source offers interesting possibilities for reductions. Carbon monoxide is a cheap and abundant chemical used on industrial scale for a variety of transformations. Although the reduction of nitroarenes with CO/H2O is known in the presence of noble-metal catalysts, earth-abundant inexpensive catalysts showing high selectivity have not yet been developed. In this respect, herein we present the use of a heterogeneous cobalt oxide catalyst (Co3O4/NGr@C), which is modified by nitrogen-doped graphene layers. Using this non-noble metal catalyst nitroarenes are reduced in high yields and good chemoselectivities.
- Westerhaus, Felix A.,Sorribes, Ivn,Wienh?fer, Gerrit,Junge, Kathrin,Beller, Matthias
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supporting information
p. 313 - 317
(2015/03/05)
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- Click chemistry on diterpenes: Anti-inflammatory activity of the acetylenic derivatives of levopimaric acid and products of their transformations
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Anti-inflammatory activity of amides of levopimaric acid (LpA) with acetylenic moiety and its esters with 4-R-triazolic substitutions was investigated using histamine-induced mice paw edema model. The synthesized LpA derivatives possess anti-inflammatory
- Vasilevsky, Sergey F.,Baranov, Denis S.,Govdi, Anastasia I.,Sorokina, Irina V.,Tolstikova, Tatyana G.,Tolstikov, Genrikh A.,Alabugin, Igor V.
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p. 145 - 157
(2014/08/18)
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- Combined spectroscopic and quantum chemical study of [trans-Ru(C≡CC6H4R1-4)2(dppe)2]n+ and [trans-Ru(C≡CC6H4R1-4)(C≡CC6H4R2-4)(dppe)2]n+ (n = 0, 1) complexes: Interpretations beyond the lowest energy conformer paradigm
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The reaction of trans-RuCl(C≡CC6H4R1-4)(dppe)2 (2: R1 = Me (a), C5H11 (b), OMe (c), CO2Me (d), NO2 (e), C≡CSiMe3 (f), C≡CBut (g), NH2 (h)), prepared in situ from reactions of [RuCl(dppe)2]OTf ([1]OTf) with terminal alkynes in CH2Cl2 solutions containing 1,8-diazabicycloundec-7-ene (DBU) and TlBF4, provides a convenient and rapid route to bis(acetylide) complexes trans-Ru(C≡CC6H4R1-4)2(dppe)2 (3a-h) and trans-Ru(C≡ CC6H4R1-4)(C≡CC6H4R2-4)(dppe)2 (4, R1 = C≡CSiMe3, R2 = NH2; 5, R1 = CO2Me, R2 = NH2; 6, R1 = CO2Me, R2 = OMe). However, even in the absence of the chloride abstracting reagent, more strongly electron donating substituents (e.g., R1 = OMe (2c), NH2 (2h)) promote sufficient ionization of the Ru-Cl bond in trans-RuCl(C≡CC6H4R -4)(dppe)2 to lead to slow conversion to bis(alkynyl) complexes 3c,h in the presence of excess alkyne and DBU. Desilylation of 2f and 3f affords 2i and 3i (R1 = C≡CH), respectively. The molecular structures of 3a-d,f-i have been determined and are reported together with the structures of the monoalkynyl complexes 2f,g,i and compared with related compounds from the literature. Complexes 3a-i and 4-6 undergo one reversible electrochemical oxidation process, which can be attributed to depopulation of an orbital with significant alkynyl ligand character. The one-electron-oxidation products [3f]?+, [3h]?+, [4]?+, and [5]?+, chosen to serve as representative examples of this family of complexes, each exhibit a series of NIR absorptions between 15000 and 5000 cm-1 which on the basis of TDDFT calculations cannot be attributed to a single, static lowest energy molecular structure. Rather, the transitions that are responsible for the absorption band envelope have varying degrees of LMCT and inter-alkynyl ligand IVCT or MLCT character that depend not only on the nature of the Rn groups but also on the ensemble of thermally populated molecular conformers in solution with various relative orientations of the metal fragment and arylethynyl moieties. (Figure Presented)
- Marqués-González, Santiago,Parthey, Matthias,Yufit, Dmitry S.,Howard, Judith A.K.,Kaupp, Martin,Low, Paul J.
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supporting information
p. 4947 - 4963
(2015/04/27)
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- Reactivity switch enabled by counterion: Highly chemoselective dimerization and hydration of terminal alkynes
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A counterion-controlled reactivity tuning in Pd-catalyzed highly chemoselective and regioselective dimerization and hydration of terminal alkynes is reported. The use of acetate as counterion favors the formation of an alkenyl alkynyl palladium intermediate which forms hitherto less reported 1,3-diaryl-substituted conjugated enynes after reductive elimination. Using chloride, which is a better leaving group, leads to anion exchange on the alkenylpalladium intermediate with hydroxide which after reductive elimination and tautomerization delivered the hydration products.
- Xu, Caixia,Du, Weiyuan,Zeng, Yi,Dai, Bin,Guo, Hao
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supporting information
p. 948 - 951
(2014/03/21)
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- Amino derivatives of indolone-N-oxide: Preparation and antiplasmodial properties
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There is an urgent need for new antimalarial drugs with novel mechanisms of action on novel targets. Indolone-N-oxides (INODs) display antimalarial properties in vitro and in vivo, but identified leads such as 6-(4-chloro-phenyl)-5-oxy-[1,3]dioxolo[4,5-f]
- Najahi, Ennaji,Rakotoarivelo, Nambinina V.,Valentin, Alexis,Nepveu, Fran?oise
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p. 369 - 375
(2014/03/21)
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- Polymethylhydrosiloxane derived palladium nanoparticles for chemo- and regioselective hydrogenation of aliphatic and aromatic nitro compounds in water
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Chemo- and regioselective hydrogenation of a wide range of aliphatic, unsaturated, aromatic and heteroaromatic nitro compounds into their corresponding amines has been achieved with highly efficient polysiloxane-stabilised "Pd" nanoparticles on NAP-magnesium oxide supports using an environmentally friendly hydrogenating agent, polymethylhydrosiloxane [PMHS] in water. Highly stable and active Pd nanoparticles were prepared by the reduction of NAP-Mg-PdCl4 with PMHS, which serves as a reducing agent as well as a capping agent. The well-dispersed palladium nanoparticles on NAP-MgO catalysts also exhibit excellent regioselectivity in the hydrogenation of dinitrobenzenes to the corresponding nitroanilines. The catalyst has high durability against sintering during the hydrogenation reaction and can be reused with no loss in its activity. This journal is the Partner Organisations 2014.
- Damodara, Dandu,Arundhathi, Racha,Ramesh Babu, T. Venkata,Legan, Margaret K.,Kumpaty, Hephzibah J.,Likhar, Pravin R.
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p. 22567 - 22574
(2014/06/23)
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- Highly efficient and selective photocatalytic hydrogenation of functionalized nitrobenzenes
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We report a simple but efficient photocatalytic nitrobenzene reduction method employing eosin Y as the photocatalyst and TEOA as the reducing agent. With green LED light irradiation, the nitro group in the nitrobenzenes containing other reducible groups was chemoselectively reduced into an amino group, and the corresponding anilines were isolated in quantitative yields. The photoinduced electron transfer mechanism suggests that the high chemoselectivity originates from the better electron-withdrawing ability of the nitro group.
- Yang, Xiu-Jie,Chen, Bin,Zheng, Li-Qiang,Wu, Li-Zhu,Tung, Chen-Ho
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supporting information
p. 1082 - 1086
(2014/03/21)
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