- A new series of N-substituted tetraphenylethene-based benzimidazoles: Aggregation-induced emission, fast-reversible mechanochromism and blue electroluminescence
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Four new N-substituted tetraphenylethene-based benzimidazoles N-R-2-(4-(1,2,2-triphenylvinyl)phenyl)-1H-benzo[d]imidazoles (R = phenyl (3a), R = 4-(tert-butyl)phenyl (3b), R = n-butyl (3c), R = n-hexyl (3d)) were synthesized conveniently by cyclization reaction of 4-tetraphenylenthenealdehyde with N-substituted ortho-nitroaniline. The four compounds exhibit typical aggregation-induced emission (AIE) property with relatively high solid state absolute fluorescence quantum yields (38.1–65.7%) and fast-recoverable mechanochromism property with solid-state fluorescence change between blue and yellow-green. They are thermally stable with decomposition temperatures above 319 °C. Both of multilayer electroluminescence devices fabricated with compounds 3b and 3c as emitters are blue emission. The turn-on voltage of device based on compound 3b is 3.3 V with maximum luminance and current efficiency of 2470 cd/m2 and 1.48 cd/A, respectively.
- Zhang, Tengfei,Zhang, Ran,Zhao, Yun,Ni, Zhonghai
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- 11-(Tetrahydro-3 and 4-pyridinyl)dibenzo[b,e][1,4]diazepines undergo novel rearrangements on treatment with concentrated HBr
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11-(1,2,5,6-Tetrahydro-1-methyl-3-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine on heating in conc. HBr afforded trans-5-(2-aminophenyl)-1,3,4,4a,5,10a-hexahydro-2-methylbenzo[b][1,6] naphthyridin-10(2H)-one in one step. The isomer 11-(1,2,5,6-tetrahydro-1-methyl-4-pyridinyl)-5-methyl-5H-dibenzo[b,e][1,4] diazepine underwent a novel rearrangement resulting in the pentacycle, 4-amino-5,13-diaza-13-methyl-bicyclo[3.3.1]nonan[6,7,8-k,l]acridine.
- Cairns, James,Clarkson, Thomas R.,Hamersma, Johan A.M.,Rae, Duncan R.
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- Copper-catalyzed arylation of amines using diphenyl pyrrolidine-2- phosphonate as the new ligand
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We have developed a general, efficient, and inexpensive catalyst system for arylation of amines by using 10 mol % of CuI as the copper source, 20 mol % of diphenyl pyrrolidine-2-phosphonate (DPP) as the ligand, K3PO 4 as the base, and DMF containing 2% water (v/v) as the solvent.
- Rao, Honghua,Fu, Hua,Jiang, Yuyang,Zhao, Yufen
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- Solution-processed efficient deep-blue fluorescent organic light-emitting diodes based on novel 9,10-diphenyl-anthracene derivatives
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A series of 9,10-diphenyl-anthracene derivatives bearing either benzimidazole or carbazole moieties as substituents were synthesized and characterized as blue emitters for organic light-emitting diodes (OLEDs). Their optical, electrochemical and thermal properties have been investigated, and their molecular structure-property relationships were evaluated. These compounds both exhibited a high glass-transition temperature (Tg ≥ 195 °C) and a high decomposition temperature (Td ≥ 494 °C). The solution processed non-doped device using CAC as a fluorescence emitter showed a maximum luminance efficiency of 1.63 cd A-1, a maximum power efficiency of 0.77 lm W-1 and a maximum external quantum efficiency of 1.53%. By introducing 1,3-bis[4-tert-butylphenyl-1,3,4-oxadiazolyl] phenylene (OXD-7):polyvinylcarbazole (PVK) as host in the emitting layer, the doped deep-blue emitting device of CAC exhibited a turn-on voltage of 4.75 V, a maximum luminance efficiency of 3.03 cd A-1, a maximum power efficiency of 1.64 lm W-1 and a maximum external quantum efficiency of 2.81%. Our results demonstrate a promising approach to well-designed materials for use in deep-blue fluorescence OLED applications. This journal is
- Zhang, Zhaohang,Jiang, Wei,Ban, Xinxin,Yang, Min,Ye, Shanghui,Huang, Bin,Sun, Yueming
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- Synthesis, photophysics, and reverse saturable absorption of bipyridyl platinum(II) bis(acetylide) complexes bearing aromatic electron-withdrawing substituents on the acetylide ligands
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Three platinum(II) bipyridyl bis((7-R-fluoren-2-yl)acetylide) complexes (R = benzoyl (Pt-1), 2-(N-phenylbenzimidazoly) (Pt-2), or 2-(3-phenylquinoxalinyl) (Pt-3)) are synthesized and characterized. Their photophysical properties and reverse saturable absorption are systematically investigated via UV-vis absorption, emission, transient absorption, and nonlinear transmission spectroscopy/technique. All three complexes possess ligand-centered 1π,π transitions below 400 nm, and a broad, featureless 1MLCT/1LLCT absorption band in the region of 400-550 nm in CH2Cl2 solutions. They are emissive in a variety of fluid solutions at room temperature and at 77 K glassy matrix. On the basis of the emission lifetime, solvatochromic effect, and thermally induced Stokes shift, the emitting states are tentatively ascribed to 3π,π/3MLCT/3LLCT states for Pt-1, and predominantly 3MLCT/3LLCT states for Pt-2 and Pt-3 in polar solvents like CH3CN. Pt-1-Pt-3 also exhibit broad triplet excited-state absorption, i.e., 425-800 nm for Pt-1 and Pt-3, and 425-725 nm for Pt-2, from the same excited states that emit. Strong reverse saturable absorption (RSA) occurs at 532 nm for ns laser pulses from all of the complexes due to the stronger triplet excited-state absorption at this wavelength, suggesting that the π-conjugated aromatic electron-withdrawing substituents at the fluorenylacetylide ligands enhance the RSA of the Pt(II) diimine bis(acetylide) complexes.
- Liu, Xu-Guang,Sun, Wenfang
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- A Simple and Efficient Flow Preparation of Pyocyanin a Virulence Factor of Pseudomonas aeruginosa
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The synthesis of the naturally occurring toxin pyocyanin has been realized in a short 4 step sequence. The key photochemical reaction and isolation of the final product have been facilitated by the use of flow chemistry techniques and immobilised reagents. Using these procedures gram quantities of pyocyanin were easily prepared in high yield and purity.
- Mortzfeld, Frederik B.,Pietruszka, J?rg,Baxendale, Ian R.
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- N-substituted benzimidazole acrylonitriles as in vitro tubulin polymerization inhibitors: Synthesis, biological activity and computational analysis
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We present the design, synthesis and biological activity of novel N-substituted benzimidazole based acrylonitriles as potential tubulin polymerization inhibitors. Their synthesis was achieved using classical linear organic and microwave assisted techniques, starting from aromatic aldehydes and N-substituted-2-cyanomethylbenzimidazoles. All newly prepared compounds were tested for their antiproliferative activity in vitro on eight human cancer cell lines and one reference non-cancerous assay. N,N-dimethylamino substituted acrylonitriles 30 and 41, bearing N-isobutyl and cyano substituents placed on the benzimidazole nuclei, showed strong and selective antiproliferative activity in the submicromolar range of inhibitory concentrations (IC50 0.2–0.6 μM), while being significantly less toxic than reference systems docetaxel and staurosporine, thus promoting them as lead compounds. Mechanism of action studies demonstrated that two most active compounds inhibited tubulin polymerization. Computational analysis confirmed the suitability of the employed benzimidazole-acrylonitrile skeleton for the binding within the colchicine binding site in tubulin, thus rationalizing the observed antitumor activities, and demonstrated that E-isomers are active substances. It also provided structural determinants affecting both the binding position and the matching affinities, identifying the attached NMe2 group as the most dominant in promoting the binding, which allows ligands to optimize favourable cation???π and hydrogen bonding interactions with Lys352.
- Perin,Hok,Be?,Persoons,Vanstreels,Daelemans,Vianello,Hranjec
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- Design, synthesis, and structure-activity relationships of novel imidazo[4,5-c]pyridine derivatives as potent non-nucleoside inhibitors of hepatitis C virus NS5B
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The hepatitis C virus (HCV) NS5B polymerase is an attractive target for the development of novel and selective inhibitors of HCV replication. In this paper, the design, synthesis, and preliminary SAR studies of novel inhibitors of HCV NS5B polymerase based on the structure of tegobuvir have been described. The efforts to optimize the antiviral potency and reduce the treatment side effects with respect to genotype 1b resulted in the discovery of compound 3, which exhibited an EC50 of 1.163 nM and a CC50 >200 nM in a cell-based HCV replicon system assay. Additionally, testing for inhibition of the hERG channel showed a marked improvement over tegobuvir and the pharmacokinetic properties of compound 3 indicated that it was worthy of further investigation as a non-nucleoside inhibitor of HCV NS5B polymerase.
- Liu, Moyi,Xu, Qiaoling,Guo, Su,Zuo, Ruixi,Hong, Yue,Luo, Yong,Li, Yingxiu,Gong, Ping,Liu, Yajing
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- Diarylamine Synthesis via Desulfinylative Smiles Rearrangement
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Diarylamines are obtained directly from sulfinamides through a novel rearrangement sequence. The transformation is transition metal-free and proceeds under mild conditions, providing facile access to highly sterically hindered diarylamines that are otherw
- Butterworth, Sam,Greaney, Michael F.,Large, Jonathan M.,Sephton, Thomas
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supporting information
(2022/02/09)
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- Ionic luminous platinum complex based on benzimidazole phosphine ligand and preparation method of ionic luminous platinum complex
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The invention relates to an ionic luminous platinum complex based on a benzimidazole phosphine ligand and a preparation method of the ionic luminous platinum complex, belonging to the technical field of synthesis of organic complexes. The molecular formula of the platinum complex is [C44H31N3PPtS]OTF, [C45H33N3OPPtS]OTF or [C45H30F3N3PPtS]OTF. The ionic luminous platinum complex has strong absorption (wherein epsilon is greater than 5 * 10 L. mol. cm ) at a wavelength of near 230 nm, medium-intensity absorption in a wavelength range of 280-360 nm and low-intensity absorption in a wavelength range of 375-430 nm; the luminous quantum efficiency of the ionic luminous platinum complex in a 293K solution and a solid state is up to 86.6% and 69.1% respectively; and the service life of the ionic luminous platinum complex in the 293K solution and the solid state is up to 6.1 microseconds and 18.9 microseconds respectively. The ionic luminous platinum complex is a high-efficiency OLED photoluminescent material and can be used in the field of preparation of OLED luminescent materials.
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Paragraph 0066; 0069-0070; 0077-0078; 0085-0086
(2021/08/25)
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- Novel 4-phenoxy pyridine derivative and application thereof
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The invention relates to a novel 4-phenoxy pyridine derivative and application thereof. The 4-phenoxy pyridine derivative has a structure as shown in a general formula (I), and the pharmacological activity test result of the novel 4-phenoxy pyridine derivative shows that the 4-phenoxy pyridine derivative has a remarkable inhibition effect on human gastric cancer cells MKN45, human lung cancer cells A549, human lung cancer cells H460 and human colon cancer cells HT-29; and meanwhile, the invention relates to a strong c-Met kinase inhibition effect of the compounds, and also relates to application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase, and application of the compounds and the pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of drugs for treating and/or preventing diseases caused by abnormal high expression of c-Met kinase. particularly relates to application in preparation of medicines for treating and/or preventing cancers.
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Paragraph 0049; 0063-0065
(2021/06/02)
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- Design, synthesis, and biological evaluation of benzo[d]imidazole-2-carboxamides as new anti-TB agents
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Tuberculosis is the leading cause of death globally among infectious diseases. Due to the development of resistance of Mycobacterium tuberculosis to currently used anti-TB medicines and the TB-HIV synergism the urgent need to develop novel anti-mycobacterial agents has been realized. The drug-to-target path has been the successful strategy for new anti-TB drug development. All the six drug candidates that have shown promise during the clinical trials and some of these being approved for treatment against MDR TB are the results of phenotype screening of small molecule compound libraries. In search of compounds belonging to novel pharmacophoric class that could be subjected to whole cell assay to generate new anti-TB leads the benzo[d]imidazole-2-carboxamide moiety has been designed as a novel anti-TB scaffold. The design was based on the identification of the benzimidazole ring as a prominent substructure of the FDA approved drugs, the structural analysis of reported anti-TB benzimidazoles, and the presence of the C-2 carboxamido functionality in novel bioisoteric anti-TB benzothiazoles. Twenty seven final compounds have been prepared via NH4Cl-catalyzed amidation of ethyl benzo[d]imidazole-2-carboxylates, as the required intermediates, obtained through a green “all water” one-pot synthetic route following a tandem N-arylation-reduction-cyclocondensation procedure. All of the synthesised target compounds were assessed for anti-TB potential using H37Rv ATCC27294 strain. Thirteen compounds were found with better MIC (0.78–6.25 μg/mL) than the standard drugs and being non-cytotoxic nature ( 60) and a few others e.g., 8a, 8f, 8k and 8o are the next best anti-TB hits (MIC: 1.56 μg/mL). The determination and analysis of various physiochemical parameters revealed favorable druglike properties of the active compounds. The compounds 8a-l and 8o, with MIC values of ≤ 6.25 μg/mL, have high LipE values (10.66–11.77) that are higher than that of the suggested value of > 6 derived from empirical evidence for quality drug candidates and highlight their therapeutic potential. The highest LipE value of 11.77 of the best active compound 8e with the MIC of 0.78 μg/mL indicates its better absorption and clearance as a probable clinical candidate for anti-TB drug discovery. These findings highlight the discovery of benzimidazole-2-carboxamides for further development as new anti-TB agents.
- Dhameliya, Tejas M.,Patel, Kshitij I.,Tiwari, Rishu,Vagolu, Siva Krishna,Panda, Dulal,Sriram, Dharmarajan,Chakraborti, Asit K.
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- Biomimetic alloxan-catalyzed intramolecular redox reaction with O2: One-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles
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Given the necessity of sacrificial reductants in various biomimetic aerobic oxygenations, alloxan-catalyzed aerobic redox system for one-pot atom-economic synthesis of sulfinyl-functionalized benzimidazoles was developed by ingeniously binding both the substrate sulfide and sacrificial reductant. This mild and transition-metal-free protocol undergoes two oxidations without additional sacrificial reagents, except for the environmentally benign molecular oxygen.
- Zhang, Shiqi,Yi, Dong,Li, Guangxun,Li, Ling,Zhao, Gang,Tang, Zhuo
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supporting information
(2020/12/25)
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- Schiff bases-titanium (III) & (IV) complex compounds: Novel photocatalysts in Buchwald-Hartwig C–N cross-coupling reaction
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Nine novel Schiff bases were derived from salicylic aldehyde and oxalic aldehyde, isolated, and their molecular and spatial structure were explored by a set of experiments (IR, CNMR, HNMR, CHN, SEM, XRD) and theoretical simulation (DFT def2-TZVP). A high potential was predicted in metal cations chelating. The isolated organic species were applied as the ligands in the reaction of complex formation with titanium (III) chloride and (IV) bromide and 12 novel complexes were synthesized and studied experimentally and theoretically. Using the UV–vis spectroscopic titration, the solution stability of the complexes was indicated. Depending on the nature of the Schiff base ligand, their formation constants were calculated in the range of 6.84–17.32. Using the DFT def2-TZVP theoretical method together with the experimental spectroscopic data, the coordination types of the ligands were investigated, and the structure of the complexes was proposed. The photocatalytic ability of the isolated complexes was tested in the C-N cross-coupling reaction under sunlight. Complexes exhibited high visible-light photocatalytic activity for a wide range of aromatic and benzylic amines including electron-withdrawing and electron-donating groups from moderate to good yields ranging in 50–85 %. The use of an inexpensive, clean, and renewable energy source (visible light) is the superiority of the developed photocatalytic systems.
- Absalan, Yahya,Ghandi, Khashayar,Gholizadeh, Mostafa,Kovalchukova, Olga,Mahmoudi, Ghodrat,Sarvestani, Hossein Sabet,Shad, Nazanin Noroozi,Strashnov, Pavel
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- A terphenyl phosphine as a highly efficient ligand for palladium-catalysed amination of aryl halides with 1° anilines
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A terphenyl phosphine ligand (2,6-bis(2,4,6-triisopropylphenyl)phenyl-dicyclohexylphosphine, TXPhos) and its supported palladium complex [(TXPhos)(allyl)PdCl] have been developed and the catalyst system is highly efficient in amination of aryl halides with 1° anilines, especially effective for densely functionalized substrates including both partners possessing ortho-ester, acetyl, nitrile and nitro groups. With the TXPhos-supported catalyst system, many partner combinations have been unprecedentedly realized and the base scope has been even extended to KOAc, which is even the best choice in the amination of 2-nitrochlorobenzene.
- Shi, Ji-cheng,Zhang, Lixue,Zhou, Fabin
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p. 238 - 243
(2021/09/07)
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- Preparation method of secondary aromatic amine
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The invention provides a method for preparing secondary aromatic amine by performing a palladium-catalyzed C-N coupling reaction on (pseudo)aryl halide and (pseudo)heterocyclic aryl halide and primary(heterocyclic)aromatic amine. The method is characterized in that an alkali for promoting the reaction is an alkali metal carboxylate or an alkali metal bicarbonate.
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Paragraph 0023
(2021/03/31)
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- Synthesis and Characterization of a Tetradentate, N-Heterocyclic Carbene Copper(II) Complex and Its Use as a Chan-Evans-Lam Coupling Catalyst
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Copper N-heterocyclic carbenes (NHCs) are an emerging area of focus for catalysis and other applications. Using a straightforward methodology, a new and highly modifiable tetradentate copper(II) NHC complex was generated and characterized using X-ray crystallography, UV-vis and EPR spectroscopy, cyclic voltammetry, and ESI-MS. This copper(II) NHC complex adopted a distorted 4-coordinate coordination mode and demonstrates a unique absorption spectrum for a copper(II) species, but more interestingly, its redox properties indicate that it can readily access all three common copper oxidation states under atmospheric conditions. The tetradentate copper(II) NHC complex was used to catalytically generate new C-N bonds from a series of phenylboronic acids and amines. Once this CEL methodology was refined, moderate to high yields were achieved using catalytic amounts of the copper(II) complex to couple phenylboronic acids to a series of aniline derivatives. Substituted phenylboronic acids and anilines had minimal impact on the catalytic capabilities of this copper complex; however, there is some indication that steric interactions between catalyst and substrates may have an impact on efficient catalysis. The straightforward synthesis of this framework and the utilization of an inexpensive, first-row transition metal center in this system highlight the usefulness of copper(II) NHCs as catalyst for cross-coupling reactions.
- Cope, James D.,Sheridan, Patrick E.,Galloway, Christopher J.,Awoyemi, Raymond Femi,Stokes, Sean L.,Emerson, Joseph P.
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p. 4457 - 4464
(2021/01/09)
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- Synthesis and characterization of new square planar heteroleptic cationic complexes [Ni(ii) β-oxodithioester-dppe]+; Their use as a catalyst for Chan-Lam coupling
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Novel heteroleptic [Ni(ii) β-oxodithioester-dppe]+PF6- complexes (β-oxodithioester = methyl-3-hydroxy-3-benzyl-2-propenedithioate L1 1, methyl-3-hydroxy-3-(p-methoxyphenyl)-2-propenedithioate L2 2, methyl-3-hydroxy-3-(naphthyl)-2-propenedithioate L3 3, methyl-3-hydroxy-3-(p-chlorophenyl)-2-propenedithioate L4 4, methyl-3-hydroxy-3-(p-bromophenyl)-2-propenedithioate L5 5 and methyl-3-hydroxy-3-(p-cyanophenyl)-2-propenedithioate L6 6) have been synthesized and characterized by elemental (C, H, N) analysis, ESI-MS, IR, UV-visible, 1H, 13C{1H}, 31P{1H} and 19F{1H} NMR spectroscopy. The distorted square planar structures of the isomorphous cationic complexes 2, 3, 4 and 5 have been determined by X-ray crystallography. The catalytic activities of 1-6 were investigated for the Chan-Lam coupling reaction involving arylboronic acids and amines to afford N-arylated products in good to excellent yields under mild conditions with 1 mol% catalyst loading. This catalytic protocol offers significant functional group tolerance, and is endowed with a broad substrate scope. This journal is
- Kumari, Kavita,Kumar, Saurabh,Singh, Krishna Nand,Drew, Michael G. B.,Singh, Nanhai
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p. 12143 - 12153
(2020/07/30)
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- One-way valveN-Preparation method of aryl substituted heterocyclic compound (by machine translation)
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The invention relates to the technical field of organic chemical synthesis, in particular to an organic chemical synthesis technology. NThe preparation method comprises ?timetime?: 3 molar ratio, reaction 30 - 60 minutes at normal temperature and normal pressure, water adding quenching after reaction, organic solvent extraction 1:1-1 and column chromatography separation (V). Petroleum ether : VEthyl acetate =40:1 - 20:1). NAryl substituted heterocyclic derivatives. Nitrobenzene is used as Ar-H source. N-methylaniline. N-ethylaniline. N-methyl-heterocycles, tetrahydroquinoline, and the like can be used as the amine source. t- BuBuBuBuBuBuBuONa/DMSO/O2 In the system, a direct arylamine reaction of the aromatic ring is achieved. This process has the advantage that the process is simple and high in atomic economy, avoiding the use of expensive transition metals, mild reaction conditions, and environmental-friendly by-products. (by machine translation)
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Paragraph 0022
(2020/11/01)
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- Heterocyclic compound and organic light emitting device including the same
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Provided are a heterocyclic compound and an organic light-emitting device including the same. The heterocyclic compound may be represented by Formula 1: in the Formula 1, A1, X2, Y1, Y2, m1, m2, R10,R20, R30, b10, b20 and b30 are same as described in the description.
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Paragraph 0550-0554
(2020/07/15)
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- A green and practical reduction of N-(4-chlorophenyl)-2-nitroaniline and its derivatives to corresponding N-substituted-benzene-1,2-diamines using thiourea dioxide
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A new effective approach for synthesizing diverse N-substituted-benzene-1,2-diamines is reported. The treatment of N-substituted-2-nitroanilines with thiourea dioxide in the presence of sodium hydroxide efficiently formed the corresponding N-substituted-benzene-1,2-diamines, including N-(4-chlorophenyl)benzene-1,2-diamine with a good yield of 94%. The by-product is environmentally-friendly urea and is easy to separate from the product by filtration procedure that enhances the convenience of the approach.
- Cui, Jian-Lan,Wang, Ning,Wang, Xiao,Yu, Si-Yuan,Zhong, Cong-Shan
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supporting information
(2020/01/22)
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- Exploration of Fragment Binding Poses Leading to Efficient Discovery of Highly Potent and Orally Effective Inhibitors of FABP4 for Anti-inflammation
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Fatty-acid binding protein 4 (FABP4) is a promising therapeutic target for immunometabolic diseases, while its potential for systemic inflammatory response syndrome treatment has not been explored. Here, a series of 2-(phenylamino)benzoic acids as novel and potent FABP4 inhibitors are rationally designed based on an interesting fragment that adopts multiple binding poses within FABP4. A fusion of these binding poses leads to the design of compound 3 with an ?460-fold improvement in binding affinity compared to the initial fragment. A subsequent structure-aided optimization upon 3 results in a promising lead (17) with the highest binding affinity among all the inhibitors, exerting a significant anti-inflammatory effect in cells and effectively attenuating a systemic inflammatory damage in mice. Our work therefore presents a good example of lead compound discovery derived from the multiple binding poses of a fragment and provides a candidate for development of drugs against inflammation-related diseases.
- Su, Haixia,Zou, Yi,Chen, Guofeng,Dou, Huixia,Xie, Hang,Yuan, Xiaojing,Zhang, Xianglei,Zhang, Naixia,Li, Minjun,Xu, Yechun
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p. 4090 - 4106
(2020/05/20)
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- 4 -phenoxypyridine compound containing quinoxalinone and application thereof (by machine translation)
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The invention belongs to the field of medicines, and particularly relates to 4 -phenoxypyridine compounds containing quinoxalinone and application thereof. The 4 -phenoxypyridine compound containing quinoxalinone has the structure of the general formula (I). The invention also relates to the application of the compound of the general formula (I) to inhibit c-Met kinase and provide 4 -phenoxypyridine compounds containing quinoxalinone and pharmaceutically acceptable salts thereof in preparation of medicines for treating and/or preventing diseases caused by abnormal high expression c-Met kinase. (by machine translation)
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Paragraph 0055; 0066-0068
(2020/07/13)
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- Design, synthesis and biological evaluation of novel 4-phenoxypyridine based 3-oxo-3,4-dihydroquinoxaline-2-carboxamide derivatives as potential c-Met kinase inhibitors
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Blocking c-Met kinase activity by small-molecule inhibitors has been identified as a promising approach for the treatment of cancers. Herein, we described the design, synthesis, and biological evaluation of a series of 4-phenoxypyridine-based 3-oxo-3,4-dihydroquinoxaline derivatives as c-Met kinase inhibitors. Inhibitory activitives against c-Met kinase evaluation indicated that most of compounds showed excellent c-Met kinase activity in vitro, and IC50 values of ten compounds (23a, 23e, 23f, 23l, 23r, 23s, 23v, 23w, 23x and 23y) were less than 10.00 nM. Notably, three of them (23v, 23w and 23y) showed remarkable potency with IC50 values of 2.31 nM, 1.91 nM and 2.44 nM, respectively, and thus they were more potent than positive control drug foretinib (c-Met, IC50 = 2.53 nM). Cytotoxic evaluation indicated the most promising compound 23w showed remarkable cytotoxicity against A549, H460 and HT-29 cell lines with IC50 values of 1.57 μM, 0.94 μM and 0.65 μM, respectively. Furthermore, the acridine orange/ethidium bromide (AO/EB) staining, cell apoptosis assays by flow cytometry, wound-healing assays and transwell migration assays on HT-29 and/or A549 cells of 23w were performed. Especially compound 23w, which displayed potent antitumor, apoptosis induction and antimetastatic activity, could be used as a promising lead for further development. Meanwhile, their preliminary structure-activity relationships (SARs) were also discussed.
- Wang, Zhen,Shi, Jiantao,Zhu, Xianglong,Zhao, Wenwen,Gong, Yilin,Hao, Xuechen,Hou, Yunlei,Liu, Yajing,Ding, Shi,Liu, Ju,Chen, Ye
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- Half-sandwich (η5-Cp?)Rh(iii) complexes of pyrazolated organo-sulfur/selenium/tellurium ligands: Efficient catalysts for base/solvent free C-N coupling of chloroarenes under aerobic conditions
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Three new pyrazolated chalcogenoether ligated Rh(iii) half-sandwich complexes (1-3) were synthesised by the thermal reaction of chalcogenoether (S, Se and Te) substituted 1H-pyrazole ligands (L1-L3) and [(η5-C5Me5)RhCl]2 in methanol. The complexes were fully characterised by various spectroscopic techniques, and the molecular structures of complexes 1 and2 were also established through single crystal X-ray crystallographic analysis, which indicates a pseudo-octahedral half-sandwich piano-stool geometry around the rhodium metal. All three complexes were found to be thermally stable and insensitive towards air and moisture. One mol% of Rh(iii) complexes (1-3) along with 10 mol% of Cu(OAc)2 were explored for the Buchwald-Hartwig type C-N coupling reactions of amine and aryl chloride. Good to excellent yields (89-92%) of the coupling products were obtained with seleno- and thio-ether functionalised pyrazolated Rh(iii) complexes (1 and 2), while an average yield (39%) was obtained with the telluro-ether functionalised complex (3). In contrast to the previously reported C-N coupling reactions the present reaction works under solvent- and base-free conditions, and the coupling reaction is accomplished in just 6 h with a high yield of the coupling product. The present methodology was also found to be efficient for a wide variety of functionalised aryl halides, and aliphatic or aromatic amines (1° and 2°). Moreover, the reaction also enables the C-N coupling of electron-withdrawing substrates and base-sensitive functionalities.
- Joshi, Raj Kumar,Sharma, Charu,Sharma, Kamal Nayan,Srivastava, Avinash Kumar
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supporting information
p. 3599 - 3606
(2020/06/10)
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- Cp*Co(iii) and Cu(OAc)2bimetallic catalysis for Buchwald-type C-N cross coupling of aryl chlorides and amines under base, inert gas & solvent-free conditions
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A strategy involving bimetallic catalysis with a combination of Cp?Co(CO)I2 and Cu(OAc)2 was used for performing Buchwald-type C-N coupling reactions of aryl chlorides with amines. The reactions proceeded at 100 °C to produce excellent yields of many of the desired C-N coupled products, in 4 h, under aerobic reaction conditions. The reactions were shown to run under base-free and solvent-free conditions, enabling this strategy to work efficiently for electron-withdrawing and base-sensitive functionalities. The presented methodology was found to be equally efficient for electron-donating functionalities as well as for primary (1°) and secondary (2°) aromatic and aliphatic amines. Moreover, the products were easily separated through the extractions of the organic aqueous layer, with this process chromatographic separations is not required.
- Srivastava, Avinash K.,Sharma, Charu,Joshi, Raj K.
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supporting information
p. 8248 - 8253
(2020/12/29)
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- URJC-1-MOF as New Heterogeneous Recyclable Catalyst for C-Heteroatom Coupling Reactions
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Guillermo Calleja and co-workers from @urjc describe URJC-1-MOF as a new heterogeneous recyclable catalyst for c-heteroatom coupling reactions. The capacity of copper-based URJC-1-MOF as a MOF catalyst in cross-coupling reactions has been evaluated, focusing on the Chan-Lam-Evans arylation-type reactions on amines and alcohols without extra additives or ligands. The extraordinary chemical and structural stability of URJC-1-MOF and its good specific surface, make this material a promising alternative to homogeneous Cu (II) catalysts for cross-coupling reactions. URJC-1-MOF showed a remarkable catalytic activity for cross-coupling C?N and C?O reactions, higher than other heterogeneous and homogeneous copper-based catalyst, such as CuO, HKUST-1, Cu?MOF-74, Cu(OAc)2 and CuSO4?5H2O. Moreover, its easy recovery by simple filtration and reusability in successive runs without any loss of activity and stability, demonstrates the potential of URJC-1-MOF as an alternative catalyst for this kind of reactions in different chemical media of industrial interest.
- Mu?oz, Antonio,Leo, Pedro,Orcajo, Gisela,Martínez, Fernando,Calleja, Guillermo
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p. 3376 - 3380
(2019/07/04)
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- Preparation and characterization of isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles as a novel magnetic catalyst for the Ullmann coupling reaction
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Isatin complexed with Cu supported on 4-(aminomethyl) benzoic acid-functionalized Fe3O4 nanoparticles (Cu-IS-AMBA-MNPs) as a new catalyst was designed, prepared and characterized by appropriate analyses. The heterogeneous reusable catalyst was successfully used for the efficient and widespread syntheses of diaryl ethers and diarylamines via the Ullmann coupling reaction. This green catalyst was easily removed, reused several times with no significant loss of its activity, and provided a clean synthesis with excellent yield and reduced time.
- Khodaei, Mohammad Mehdi,Alizadeh, Abdolhamid,Haghipour, Maryam
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p. 2727 - 2747
(2019/02/13)
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- Recyclable bimetallic CuMoO4 nanoparticles for C-N cross-coupling reaction under mild conditions
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Herein we disclosed inexpensive copper(ii) bimetallic CuMoO4 nanoparticles for the C-N cross-coupling reaction of alkyl and aryl amines with haloarenes. The reaction proceeds under mild and ligand free conditions. The catalyst is recyclable and effective for a wide range of amines and haloarenes. Here, the efficiency of the Cu(ii) catalyst is increased by doping molybdenum metal. The bimetallic nanoparticles are anticipated to proceed via normal oxidative addition and reductive eliminations.
- Panigrahi, Reba,Panda, Subhalaxmi,Behera, Pradyota Kumar,Sahu, Santosh Kumar,Rout, Laxmidhar
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supporting information
p. 19274 - 19278
(2019/12/24)
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- Imidazo[4,5-c]pyridine derivative and application thereof
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The invention relates to a novel imidazo[4,5-c]pyridine derivative represented by a general formula I, and pharmaceutically acceptable salts, solvates or prodrugs of the novel imidazo[4,5-c]pyridine derivative, wherein the substituent R and R' are defined as in the specification. The invention also relates to an effect of the compound represented by the general formula I in inhibiting an NS5B RNA-dependent RNA polymerase (NS5B polymerase for short) which is necessary in a replication process of hepatitis c virus, also relates to an application of the compound, and pharmaceutically acceptable salts, hydrates or prodrugs of the compound in preparation of medicines for treating viral diseases, and especially relates to an application in preparation of medicines for treating and/or preventinghepatitis c.
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Paragraph 0135; 0150; 0151; 0152
(2019/10/01)
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- Synthesis, anticancer activity and molecular docking studies on 1,2-diarylbenzimidazole analogues as anti-tubulin agents
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Twenty-four 1,2-diarylbenzimidazole derivatives were designed, synthesized and biologically evaluated. It turned out that most of them were potential anticancer drugs. Among them, compound c24 showed the highest anti-tumor activity (GI50 = 0.71–2.41 μM against HeLa, HepG2, A549 and MCF-7 cells), and low toxicity to normal cells (CC50 > 100 μM against L02 cells). In the microtubule binding assay, c24 showed the most potent inhibition of microtubule polymerization (IC50 = 8.47 μM). The binding ability of compound c24 to tubulin crystal was verified by molecular docking simulation experiment. Further studies on HepG2 and HeLa cells showed that compound c24 could cause mitotic arrest of tumor cells to G2/M phase then inducing apoptosis. To sum up, compound c24 is a promising microtubule assembly inhibitor.
- Zhang, Ya-Liang,Yang, Rong,Xia, Lin-Ying,Man, Ruo-Jun,Chu, Yi-Chun,Jiang, Ai-Qin,Wang, Zhong-Chang,Zhu, Hai-Liang
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- Immobilization of nickel ions onto the magnetic nanocomposite based on cross-linked melamine groups: Effective heterogeneous catalyst for N-Arylation of Arylboronic acids
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A new magnetic heterogeneous catalyst was synthesized by immobilization of nickel ions onto a cross-linked polymeric nanocomposite composed of cyanuric chloride, ethylenediamine and functionalized magnetic nanoparticles. The resulting nitrogen rich support was capable of adsorbing large amounts of nickel ions (1.20 mmol g?1). The synthesized catalyst was characterized using AAS, TEM, FT-IR, EDX, TGA, SEM, BET and XRD techniques. The performance of the prepared catalyst was investigated in the C-N coupling of arylamines with aryl boronic acids. The reaction was carried out under a mild condition and good to moderate to good yields of products was obtained using only 5.0 mol% of the catalyst. The catalyst was easily recovered and reused for at least 7 times without any significant loss of its activity.
- Pourjavadi, Ali,Keshavarzi, Nahid,Moghaddam, Firouz Matloubi,Hosseini, Seyed Hassan
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- Synthesis of Di(hetero)arylamines from Nitrosoarenes and Boronic Acids: A General, Mild, and Transition-Metal-Free Coupling
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The synthesis of di(hetero)arylamines by a transition-metal-free cross-coupling between nitrosoarenes and boronic acids is reported. The procedure is experimentally simple, fast, mild, and scalable and has a wide functional group tolerance, including carbonyls, nitro, halogens, free OH and NH groups. It also permits the synthesis of sterically hindered compounds.
- Roscales, Silvia,Csák?, Aurelio G.
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p. 1667 - 1671
(2018/03/23)
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- Construction of Druglike 2-Amido Benzo[ d]imidazole Analogues via Desulfurative Cyclization of Thiourea Intermediate Resin on Solid-Phase
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A 2-amido benzo[d]imidazole library has been constructed by solid-phase synthesis. The key step of this solid-phase synthesis involves the preparation of polymer-bound 2-amino benzo[d]imidazole resin through desulfurative cyclization of thiourea resin using 2-chloro-1,3-dimethylimidazolinium chloride and N,N-diisopropylethylamine in dichloromethane (DCM), and the resin is then functionalized by acylation at the 2-amine position to afford 2-amidobenzo[d]imidazole resin. In the case of 2-amidobenzo[d]imidazole resin having a p-I or m-NO2, the resin was further functionalized by Suzuki/Sonogashira-coupling (p-I) and reduction to the primary amine (m-NO2) followed by acylation. Finally, the functionalized 2-amido-benzo[d]imidazole resin was cleaved from the polymer support by treatment with a cocktail of trifluoroacetic acid and DCM. As a result, we obtained 2-amidobenzo[d]imidazole analogues in high yield and good purities.
- Ryu, Hyun-Jeong,Yang, Seung-Ju,Lee, Gee-Hyung,Gong, Young-Dae
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supporting information
p. 282 - 291
(2018/05/24)
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- Quinoxalinone-containing 4-phenoxy substituted quinoline compound and application thereof
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The invention relates to quinoxalinone-containing 4-phenoxy substituted quinoline derivatives shown as a general formula I and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof, wherein the substituent groups Ar, R1, R2 and n have meanings as shown in the description. The invention further relates to a compound with the general formula I having a strong effect of inhibitingc-Met kinase, and further relates to application of the compounds and pharmaceutically acceptable salts, hydrates, solvates or prodrugs thereof in preparation of medicines for treating and/or preventing diseases caused by abnormal high expression of the c-Met kinase, particularly application in preparation of medicines for treating and/or preventing cancers.
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-
Paragraph 0132; 0133
(2018/10/11)
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- Tetraphenylethylene-based blue light material containing benzimidazole unit as well as preparation method and application
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The invention discloses a tetraphenylethylene-based blue light material containing a benzimidazole unit. The tetraphenylethylene-based blue light material is shown as a structural formula I or II, wherein R1 is H, tert-butyl, n-butyl or hydroxyl, and R2 is alkyl. A 2-nitro-N-tert-butylphenyl amine or 2-nitro-N-n-butylphenyl amine precursor and a 4-formyl tetraphenylethylene precursor is firstly prepared, and then cyclization reaction is carried out to prepare a compound shown as the formula I or II. A preparation method of the compound is easy to operate, the reaction is moderate and the yield is high; the compound has relatively high decomposition temperature and glass-transition temperature, and shows blue fluorescence; the compound has a relatively good single-color property, so that an OLED (Organic Light Emitting Diode) device prepared by taking the compound as a luminescent material emits blue light; the starting voltage is 3.3V and the maximum brightness efficiency is 1.48cd/A. (The formula I and the formula II are shown in the description).
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Paragraph 0027; 0028; 0029; 0036; 0037; 0038
(2017/10/10)
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- Design, synthesis and biological evaluation of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety as c-Met kinase inhibitors
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A series of novel 4-phenoxyquinoline derivatives containing 3-oxo-3,4-dihydroquinoxaline moiety were synthesized and evaluated for their c-Met kinase inhibitory activity and antiproliferative activity against five cancer cell lines (HT-29, H460, A549, MKN-45 and U87MG) in vitro. Most of the compounds exhibited moderate-to-significant cytotoxicity as compared with foretinib. The most promising compound 41 (with c-Met IC50 value of 0.90?nM) showed remarkable cytotoxicity against HT-29, H460, A549, MKN-45 and U87MG cell lines with IC50 values of 0.06?μM, 0.05?μM, 0.18?μM, 0.023?μM and 0.66?μM, respectively, and thus it was 1.22- to 3.50-fold more potent than foretinib. Their preliminary structure-activity relationships (SARs) studies indicate that electron-withdrawing groups on the terminal phenyl rings are beneficial for improving the antitumor activity.
- Liu, Ju,Yang, Di,Yang, Xiuxiu,Nie, Minhua,Wu, Guodong,Wang, Zhunchao,Li, Wei,Liu, Yajing,Gong, Ping
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p. 4475 - 4486
(2017/07/22)
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- Copper immobilized on magnetite nanoparticles coated with ascorbic acid: An efficient and reusable catalyst for C─N and C─O cross-coupling reactions
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In a continuation of using magnetic nanoparticle (MNP)-supported catalysts, ascorbic acid (readily available, very safe and with strong affinity to MNPs) was used instead of the commonly used silica layer coating. This hybrid was used for immobilizing copper nanoparticles to produce Cu/ascorbic acid@MNPs catalyst. The catalyst was characterized and used in carbon–oxygen and carbon–nitrogen (various substrates) cross-coupling reactions in aqueous media and at room temperature with excellent product yields. Furthermore, the catalyst could be quickly and completely recovered using an external magnetic field and reused for six reaction cycles without significant change in catalytic activity.
- Hajipour, Abdol R.,Check, Maryam,Khorsandi, Zahra
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- Three Different Reactions, One Catalyst: A Cu(I) PNP Pincer Complex as Catalyst for C-C and C-N Cross-Couplings
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An air-stable, thermally robust, and well-defined Cu(I) PNP pincer complex based on the 2,6-diaminopyridine scaffold is described. This complex is an active catalyst for the cross-couplings of a range of aryl and heteroaryl (including benzoxazole, thiazole, pyridine, and thiophene) halides with different organomagnesium reagents, alkynes, and aryl-amines giving excellent to good isolated yields.
- Mastalir, Matthias,Pittenauer, Ernst,St?ger, Berthold,Allmaier, Günter,Kirchner, Karl
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supporting information
p. 2178 - 2181
(2017/04/28)
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- Design, synthesis and antifungal activity of novel fenfuram-diarylamine hybrids
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Ten novel fenfuram-diarylamine hybrids were designed and synthesized. And their antifungal activities against four phytopathogenic fungi have been evaluated in vitro and most of the compounds demonstrated a significant antifungal activities against Rhizoctonia solani and Sclerotinia sclerotiorum. Compound 5e exhibited the most potent antifungal activity against R. solani with an EC50value of 0.037 mg/L, far superior to the commercially available fungicide boscalid (EC50= 1.71 mg/L) and lead fungicide fenfuram (EC50= 6.18 mg/L). Furthermore, scanning electron microscopy images showed that the mycelia on treated media grew abnormally with tenuous, wizened and overlapping colonies compared to the negative control. Molecular docking studies revealed that compound 5e featured a higher affinity for succinate dehydrogenase (SDH) than fenfuram. Furthermore, it was shown that the 3-chlorophenyl group in compound 5e formed a CH-π interaction with B/Trp-206 and a Cl-π interaction with D/Tyr-128, rendering compound 5e more active than fenfuram against SDH.
- Wang, Hongyu,Gao, Xuheng,Zhang, Xiaoxiao,Jin, Hong,Tao, Ke,Hou, Taiping
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supporting information
p. 90 - 93
(2016/12/09)
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- Synthesis and biological evaluation of novel pyrazole carboxamide with diarylamine-modi?ed scaffold as potent antifungal agents
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Twenty-seven novel pyrazole carboxamides with diarylamine-modi?ed scaffold were designed, synthesized and characterized in detail via 1H NMR, 13C NMR, IR and ESI-HRMS. Preliminary bioassays showed that some of the target compounds exhibited good antifungal activity against Rhizoctonia solani, Rhizoctonia cerealis and Sclerotinia sclerotiorum. Among them, compound 9c-7 exhibited the highest antifungal activities against R. solani, R. cerealis and S. sclerotiorum in vitro with IC50 values of 0.013, 1.608 and 1.874?μg/mL, respectively. Notably, compound 9c-7 still presented the highest fungicidal activities against R. solani in vivo with an IC50 value of 22.21?μg/mL. Molecular docking simulation results reveal that compound 9c-7 binds well to the hydrophobic pockets of the receptor protein succinate dehydrogenase. This study suggests that compound 9c-7 could act as a potential fungicide to be used for further optimization.
- Zhang, Xiao-Xiao,Jin, Hong,Deng, Yuan-Jie,Gao, Xu-Heng,Li, Yong,Zhao, Yong-Tian,Tao, Ke,Hou, Tai-Ping
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p. 1731 - 1736
(2017/07/27)
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- A method for preparing aromatic amine derivative
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The invention discloses a preparation method of a diarylamine ramification. The preparation method comprises the following steps: dissolving a phenylamine ramification, a phenylhydrazine ramification, a metal phthalocyanine ramification and a copper salt into a solvent, and reacting at -10 to 40 DEG C to obtain the diarylamine ramification. According to the preparation method, the phenylamine ramification and the phenylhydrazine ramification are taken as starting materials, so that raw materials are easy to obtain and plenty in variety; a product obtained by utilizing the method is plenty in type, can not only be directly used, but also be used for other further reactions; and no additive is required to be added. The preparation method disclosed by the invention has the advantages of short synthetic route, moderation in reaction condition, simple reaction operation and post-processing process, high yield and suitability for large-scale production.
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Paragraph 0101-0104
(2016/10/08)
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- CoPc/Cu(OAc)2-catalyzed N-arylation of amines with arylhydrazines leading to N-aryl amines
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The N-arylation of amines with arylhydrazines has been developed, achieving the selective cross-coupling of aryl radicals with amines to form N-aryl amines. The reaction uses air as an oxidant, CoPc and Cu(OAc)2as catalysts. The reaction proceeds under mild conditions in air through a relay process, arylhydrazines are oxidized to aryldiazenes by CoPc, further oxidized to aryl radicals by air (O2), which are trapped by Cu(OAc)2–amine complex, followed by reduction–elimination reaction to form N-aryl amines. Arylamines and arylhydrazines give the highest yields, but N-aryl-N-alkylamines and N-alkylamines can be used as well.
- Sun, Wang-Bin,Zhang, Pei-Zhi,Jiang, Tao,Li, Cheng-Kun,An, Li-Tao,Shoberu, Adedamola,Zou, Jian-Ping
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p. 6477 - 6483
(2016/09/23)
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- Oxidative nucleophilic aromatic amination of nitrobenzenes
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Nitrobenzenes substituted with electron-acceptor groups such as halogen, nitro, trifluoromethyl, pentafluorosulfanyl, or cyano underwent oxidative nucleophilic substitution with lithium salts of arylamines to afford N-aryl-2-nitroanilines.
- Khutorianskyi,Sonawane,Po?ta,Klepetá?ová,Beier
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supporting information
p. 7237 - 7240
(2016/06/09)
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- Facile aromatic nucleophilic substitution (SNAr) reactions in ionic liquids: An electrophile-nucleophile dual activation by [Omim]Br for the reaction
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A facile aromatic nucleophilic substitution (SNAr) reaction in recyclable [Omim]Br under relatively mild conditions has been described. An electrophile-nucleophile dual activation by [Omim]Br is also discovered based on control experiments, 1H NMR and IR spectroscopies. This chemistry provides an efficient and metal-free approach for the generation of Caryl-X (XS, N, O) bonds, many of which are significant synthetic intermediates or drugs, making this methodology attractive to both synthetic and medicinal chemistry.
- Zhang, Xiao,Lu, Guo-Ping,Cai, Chun
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p. 5580 - 5585
(2016/10/21)
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- CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acids with amides and anilines
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CuSO4-mediated decarboxylative C-N cross-coupling of aromatic carboxylic acid with amide has been developed, leading to N-arylamides in modest to excellent yields. Anilines bearing electron-withdrawing substituents could also couple efficiently
- Sheng, Wei-Jian,Ye, Qing,Yu, Wu-Bin,Liu, Ren-Rong,Xu, Meng,Gao, Jian-Rong,Jia, Yi-Xia
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supporting information
p. 599 - 601
(2015/02/19)
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- Ruthenium and palladium complexes incorporating amino-azo-phenol ligands: Synthesis, characterization, structure and reactivity
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The ligands 2-((2-aminophenyl)diazenyl)phenol, HOL1-NH2, 1a; 2-((2-aminophenyl)diazenyl)-5-methylphenol, HOL2-NH2, 1b; and 2-((2-aminophenyl) diazenyl)-5-chlorophenol, HOL3-NH2, 1c, which are abbreviated as HOL-NH2, 1, afforded the complexes of compositions [(OL-NH)Pd(PPh3)], 2, and [(OL-NH)Ru(CO)(PPh3)2], 3, upon reaction with Na2PdCl4 and Ru(CO)3(PPh3)3 respectively. In all the complexes the metals ions, Pd(II) or Ru(II), are coordinated by deprotonated ligand (OL-NH)2- in tridentate (N, N, O) fashion. X-ray structures of [(OL2-NH)Pd(PPh3)], 2b, and [(OL1-NH)Ru(CO)(PPh3)2], 3a, were determined to confirm the molecular structures. The cyclic voltammograms of [(OL-NH)Ru(CO)(PPh3)2] exhibited two quasi reversible oxidative response near 0.25 and 1.12 V vs. SCE. The nature of HOMO as obtained by DFT calculations has been inspected to have an insight into the redox orbitals. The newly synthesized [(OL-NH)Pd(PPh3)], 2a, complexes exhibited catalytic activity toward the Suzuki, Heck, Cyanation and amination reactions. Catalytic activity of complex [(OL1-NH)Ru(CO)(PPh3)2], 3a, was examined for the conversion of ketones to corresponding alcohols by transfer hydrogen reactions.
- Pattanayak, Poulami,Parua, Sankar Prasad,Patra, Debprasad,Lai,Brand?o, Paula,Felix, Vitor,Chattopadhyay, Surajit
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p. 122 - 131
(2015/03/04)
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- Imidoyl dichlorides as new reagents for the rapid formation of 2-aminobenzimidazoles and related azoles
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The development of a reagent for the efficient synthesis of five- and six-membered azoles at room temperature is proposed. A variety of substituted 2-aminobenzimidazoles are synthesized in good to excellent yields. The ability to incorporate various protecting groups makes the imidoyl dichloride reagent amenable to a large number of syntheses. The reagent is applied to the total synthesis of the 2-aminobenzimidazole containing carcinogen, 2-amino-1-methyl-6-phenylimidazo[4,5-b]pyridine (PhIP), from 2-chloro-3-nitropyridine in >60% yield in 6 steps.
- Pollock, Julie A.,Kim, Sung Hoon,Katzenellenbogen, John A.
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p. 6097 - 6099
(2015/10/28)
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- A low-cost phenylbenzoimidazole containing electron transport material for efficient green phosphorescent and thermally activated delayed fluorescent OLEDs
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A new phenylbenzoimidazole-based electron-transport material (ETM), 2,4,6-tris(2-phenyl-1H-benzo[d]imidazol-1-yl)benzonitrile (iTPBI-CN), is designed and synthesized through a simple low-cost one-step C-N coupling reaction by using 2,4,6,-trifluorobenzonitrile and 2-phenyl-1H-benzo[d]imidazole as the starting materials. In comparison with the four step synthesis of commercial ETM of 2,2,2-(1,3,5-phenylene)-tris(1-phenyl-1H-benzimidazole) (TBPI), the introduction of a cyano moiety into iTPBI-CN greatly simplifies the synthetic procedure and allows for an isomerized linkage of phenylbenzoimidazole. The glass transition temperature increases from 124 °C of TPBI to 139 °C of iTPBI-CN. Both compounds show similar HOMO levels of ～5.9 eV and a triplet energy of ～2.6 eV. The deeper LUMO level of iTPBI-CN (2.79 eV) than TPBI (2.38 eV) allows for more efficient electron-injection and a much higher device efficiency. Solution-processed green phosphorescent OLEDs with the structure of ITO/PEDOT:PSS/host:Ir(mppy)3/iTPBI-CN versus TPBI/LiF/Al show maximum current and power efficiencies of 37.7 cd A-1 and 29.0 lm W-1versus 26.1 cd A-1, 12.2 lm W-1 in the CBP host and 31.3 cd A-1 and 23.9 lm W-1versus 20.6 cd A-1, 7.4 lm W-1 in the mCP host. Furthermore, the superior device performance of iTPBI-CN over TPBI is also found in both CBP and mCP hosted green thermally activated delayed fluorescence (TADF) devices by using 2,3,5,6-tetracarbazole-4-cyano-pyridine (4CzCNPy) as a dopant.
- Wang, Fangfang,Hu, Jia,Cao, Xudong,Yang, Tao,Tao, Youtian,Mei, Ling,Zhang, Xinwen,Huang, Wei
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p. 5533 - 5540
(2015/06/08)
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- Cu(0)@Al2O3/SiO2 NPs: An efficient reusable catalyst for the cross coupling reactions of aryl chlorides with amines and anilines
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The C-N cross coupling reaction of aryl chlorides with various alkyl/aryl amines catalyzed by copper nanoparticles impregnated on alumina/silica support (Cu(0)@Al2O3/SiO2) was investigated. The prepared catalyst was characterized for its intrinsic physico-chemical and textural properties using XRD, XPS, HR-TEM, BET surface area, SEM-EDAX, H2-TPR and ICP-AES techniques. The catalyst exhibits excellent reactivity and efficacy in the cross-coupling of a wide range of alkyl/aryl amines including challenging anilines with aryl chlorides. The catalyst offers significant advantages such as brevity, milder reaction conditions, excellent yields and high functional group tolerance for C-N cross coupling when compared with the other reported methods. Moreover, this atom-economical methodology does not require an additional ligand or co-catalyst/activator. The Cu(0)@Al2O3/SiO2 catalyst was efficiently applied to a gram scale synthesis of 7-chloro-4-(4-(2-nitrophenyl)piperazin-1-yl)quinolone (2k). The robustness of the catalyst was examined by reusing it for five consecutive runs.
- Reddy, P. Linga,Arundhathi,Rawat, Diwan S.
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p. 92121 - 92127
(2015/11/17)
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- 2,6-Bis(diphenylphosphino)pyridine: A simple ligand showing high performance in palladium-catalyzed CN coupling reactions
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The use of commercially available 2,6-bis(diphenylphosphino)pyridine as a ligand in conjunction with K2CO3, DMAc and TBAB is an effective method for the palladium-catalyzed CN coupling of a variety of aryl halides with anilines, N-heterocyclic aromatic amines, and a cyclic secondary amine. The reactions proceed in good to excellent yield (up to 98%) while the loading of Pd(OAc)2 was as low as 0.025 mol %.
- Nadri, Shirin,Rafiee, Ezzat,Jamali, Sirous,Joshaghani, Mohammad
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p. 4098 - 4101
(2014/07/22)
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- Metal-free synthesis of secondary arylamines: An aliphatic-to-aromatic transformation
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An efficient method for the N-arylation of primary and some secondary amines using 2-halocyclohex-2-enones in an aliphatic-to-aromatic transformation in the presence of a substoichiometric amount of pTsOH has been developed. A series of arylamines have been synthesized from 2-halocyclohex-2-enones by in situ enamine formation followed by aromatization under environmentally friendly conditions using pTsOH. This metal-free, practical, relatively inexpensive protocol is of value in organic synthesis for industrial and academic applications. Copyright
- Barros, M. Teresa,Dey, Suvendu S.,Maycock, Christopher D.
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supporting information
p. 742 - 747
(2013/03/13)
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