- Thermally stable and robust gadolinium-based metal-organic framework: Synthesis, structure and heterogeneous catalytic O-arylation reaction
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Hydrothermal treatment of gadolinium nitrate and 2,6-naphthalenedicarboxylic acid (H2NDC) afforded a new metal-organic framework compound, {[Gd4(NDC)6(H2O)6]·2H2O}n(1). Compound 1 has been characterized by single-crystal X-ray crystallography, elemental analysis, FT-IR spectroscopy, therrmogravimetric analysis (TGA) and powder X-ray diffraction analysis. It is crystallized in the monoclinic system with the P21/n space group. Four crystallographically distinct Gd (III) centres are interconnected with each other through bridged carboxylato oxygen atoms and water molecules to form tetranuclear secondary building units, which are further connected through the carboxylato ligand and the network propagates along the crystallographic ac plane to form a 2D structure. Subsequent reinforcement from the remaining carboxylato oxygen atoms gives rise to a robust 3D framework structure. Thermogravimetric analysis demonstrates that compound 1 is fairly stable after dehydration under a nitrogen atmosphere. Notably, compound 1 is capable of catalyzing the O-arylation reaction efficiently between substituted phenols and bromoarene under heterogeneous conditions at 80 °C to afford unsymmetrical diarylethers.
- Ghosh, Pameli,Maity, Tanmoy,Biswas, Saptarshi,Debnath, Rakesh,Koner, Subratanath
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- Vinyl sulfonamide or vinyl amide compound as well as preparation method and application thereof (by machine translation)
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The structure is shown in the formula I, and the definition of each substituent is as described in the specification and the claims. The compounds of the invention are useful in the preparation of medicaments for the treatment of diseases or disorders mediated by TEAADs. (by machine translation)
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Paragraph 0132-0135
(2020/12/14)
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- CoII Immobilized on Aminated Magnetic-Based Metal–Organic Framework: An Efficient Heterogeneous Nanostructured Catalyst for the C–O Cross-Coupling Reaction in Solvent-Free Conditions
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Abstract: In this paper, we report the synthesis of Fe3O4?AMCA-MIL53(Al)-NH2-CoII NPs based on the metal–organic framework structures as a magnetically separable and environmentally friendly heterogeneous nanocatalyst. The prepared nanostructured catalyst efficiently promotes the C–O cross-coupling reaction in solvent-free conditions without the need for using toxic solvents and/or expensive palladium catalyst. Graphic Abstract: [Figure not available: see fulltext.].
- Mohammadinezhad, Arezou,Akhlaghinia, Batool
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p. 332 - 352
(2020/01/11)
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- Discovery and biological evaluation of vinylsulfonamide derivatives as highly potent, covalent TEAD autopalmitoylation inhibitors
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Transcriptional enhancer associated domain family members (TEADs) are the most important downstream effectors that play the pivotal role in the development, regeneration and tissue homeostasis. Recent biochemical studies have demonstrated that TEADs could undergo autopalmitoylation that is indispensable for its function making the lipid-binding pocket an attractive target for chemical intervention. Herein, through structure-based virtual screen and rational medicinal chemistry optimization, we identified DC-TEADin02 as the most potent, selective, covalent TEAD autopalmitoylation inhibitor with the IC50 value of 197 ± 19 nM while it showed minimal effect on TEAD-YAP interaction. Further biochemical counter-screens demonstrate the specific thiol reactivity and selectivity of DC-TEADin02 over the kinase family, lipid-binding proteins and epigenetic targets. Notably, DC-TEADin02 inhibited TEADs transcription activity leading to downregulation of YAP-related downstream gene expression. Taken together, our findings proved the validity of modulating transcriptional output in the Hippo signaling pathway through irreversible chemical interventions of TEADs autopalmitoylation activity, which may serve as a qualified chemical tool for TEADs palmitoylation-related studies in the future.
- Lu, Wenchao,Wang, Jun,Li, Yong,Tao, Hongru,Xiong, Huan,Lian, Fulin,Gao, Jing,Ma, Hongna,Lu, Tian,Zhang, Dan,Ye, Xiaoqing,Ding, Hong,Yue, Liyan,Zhang, Yuanyuan,Tang, Huanyu,Zhang, Naixia,Yang, Yaxi,Jiang, Hualiang,Chen, Kaixian,Zhou, Bing,Luo, Cheng
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- Design of BNPs-TAPC Palladium Complex as a Reusable Heterogeneous Nanocatalyst for the O-Arylation of Phenols and N-Arylation of Amines
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The thermally stable new heterogenous nanocatalyst BNPs@SiO2(CH2)3-TAPC-O-CH2CH2NH2-Pd(0) was synthesized, characterized and successfully applied in carbon-heteroatom (C–O and C–N) coupling reactions of aryl halides with phenols and amines. The formation of resultant nanocatalyst was approved by FT-IR, XRD, TGA, XPS and EDX techniques. The morphology of BNPs@SiO2(CH2)3-TAPC-O-CH2CH2NH2-Pd(0) was characterized using scanning and transmission electron microscopes. The leaching of palladium from the surface of the catalyst was studid by ICP-OES technique. Noteworthy, the highly active BNPs@SiO2(CH2)3-TAPC-O-CH2CH2NH2-Pd(0) can be easily recycled and reused for six times with negligible loss in its activity. Some remarkable advantages of this method are the shorter reaction times, milder conditions, no needs for an inert atmosphere, high yields and easy separation. Graphical Abstract: [Figure not available: see fulltext.].
- Bahrami, Kiumars,Khodamorady, Minoo
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p. 688 - 698
(2019/01/04)
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- Magnetically recyclable nano copper/chitosan in O-arylation of phenols with aryl halides
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Interaction of chitosan (CS) with Fe3O4, followed by embedding Cu nanoparticles (NPs) on the magnetic surface through adsorption of Cu2+, and its reduction to Cuo via NaBH4, offers a reusable efficient catalyst (Fe3O4/CS-Cu NPs) that is employed in cross-coupling reactions of aryl halides with phenols, which affords the corresponding diaryl ethers, with good to excellent yields. The catalyst is completely recoverable from the reaction mixture by using an external magnet. It can be reused four times, without significant loss in its catalytic activity.
- Mousavi Mashhadi, Seyed Ali,Kassaee, Mohamad Z.,Eidi, Esmaiel
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- Novel cobalt-valine catalyzed O-arylation of phenols with electron deficient aryl iodides
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Abstract: A Novel cobalt-catalyzed O-arylation of phenols with electron deficient aryl iodides is described. The reaction employs cheap and easy-to-handle cobalt acetate tetrahydrate as the catalyst precursor and naturally occurring l-valine as the ligand without the use of any transmetallating or reducing agents. The new protocol offers a wide scope for a variety of phenols towards O-arylation with moderate to excellent yields with electron deficient aryl iodides.
- Ujwaldev, Sankuviruthiyil M.,Saranya, Salim,Harry, Nissy Ann,Anilkumar, Gopinathan
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p. 339 - 346
(2019/01/18)
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- Immobilized palladium nanoparticles on MNPs@A-N-AEB as an efficient catalyst for C-O bond formation in water as a green Solvent
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Palladium nanoparticles immobilized on the magnetic nanoparticles@2-amino-N-(2-aminoethyl) benzamide (MNPs@A-N-AEB.Pd0) have been presented as an efficient, and reusable magnetically heterogeneous catalyst for the C-O coupling reaction, namely Ullmann condensation reactions in an aqueous medium. This heterogeneous catalyst shows superior reactivity for the C-O arylation of different aryl halide (chloride, bromide, and iodide) with phenol derivatives to afford the desired products in good to excellent yields within short reaction time. Moreover, the catalyst can be easily recovered and reused for seven runs without loss of catalytic activity. The catalyst was characterized by several techniques, such as FT-IR, SEM, TEM, EDS, XRD, TGA and ICP-OES.
- Moghaddam, Firouz Matloubi,Eslami, Mohammad
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- A green approach for arylation of phenols using iron catalysis in water under aerobic conditions
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The first efficient iron-catalyzed coupling of aryl iodides with phenols was developed exclusively with water as solvent. The reaction is performed with low cost and readily available FeCl3·6H2O and DMEDA catalytic system providing diaryl ethers in good to excellent yields. The effectiveness of this reaction was further revealed by compatibility with a wide range of functional groups. Moreover, the procedure is rendered simple as this transformation is carried out in the presence of air. Thus, the protocol represents a facile, economical and eco-friendly procedure to access diaryl ethers.
- Sindhu, Kallikkakam S.,Ujwaldev, Sankuviruthiyil M.,Keerthi Krishnan,Anilkumar, Gopinathan
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p. 146 - 150
(2017/03/17)
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- Structure-based design of N-substituted 1-hydroxy-4-sulfamoyl-2-naphthoates as selective inhibitors of the Mcl-1 oncoprotein
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Structure-based drug design was utilized to develop novel, 1-hydroxy-2-naphthoate-based small-molecule inhibitors of Mcl-1. Ligand design was driven by exploiting a salt bridge with R263 and interactions with the p2 pocket of the protein. Significantly, target molecules were accessed in just two synthetic steps, suggesting further optimization will require minimal synthetic effort. Molecular modeling using the Site-Identification by Ligand Competitive Saturation (SILCS) approach was used to qualitatively direct ligand design as well as develop quantitative models for inhibitor binding affinity to Mcl-1 and the Bcl-2 relative Bcl-xL as well as for the specificity of binding to the two proteins. Results indicated hydrophobic interactions in the p2 pocket dominated affinity of the most favourable binding ligand (3bl: Ki = 31 nM). Compounds were up to 19-fold selective for Mcl-1 over Bcl-xL. Selectivity of the inhibitors was driven by interactions with the deeper p2 pocket in Mcl-1 versus Bcl-xL. The SILCS-based SAR of the present compounds represents the foundation for the development of Mcl-1 specific inhibitors with the potential to treat a wide range of solid tumours and hematological cancers, including acute myeloid leukemia.
- Lanning, Maryanna E.,Yu, Wenbo,Yap, Jeremy L.,Chauhan, Jay,Chen, Lijia,Whiting, Ellis,Pidugu, Lakshmi S.,Atkinson, Tyler,Bailey, Hala,Li, Willy,Roth, Braden M.,Hynicka, Lauren,Chesko, Kirsty,Toth, Eric A.,Shapiro, Paul,MacKerell, Alexander D.,Wilder, Paul T.,Fletcher, Steven
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p. 273 - 292
(2016/03/22)
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- Ullmann Coupling Reaction of Nitro-Substituted Aryl Halides with Phenols under Mild Conditions: Micro-/Mesoporous Hierarchical LaAlPO-5 Zeolite Catalyst
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Heterogeneous catalytic reactions of aromatic organic molecules over zeolite catalysts present many challenges because of the shape selectivity of the micropores of conventional zeolites that limits the diffusion of aromatic molecules. Herein, Ullmann coupling reactions of phenols with nitro-substituted aryl halides were catalyzed by rare-earth-doped mesoporous AlPO-5 zeolites in the absence of ligands. The AlPO-5-MAlPO-5-M zeolites had a pure AFI structure and consisted of spherical particles assembled by nanofibers. The rare-earth elements were highly dispersed in the AlPO-5-MAlPO-5-M samples. The LaAlPO-5-MAlPO-5-M zeolite is an excellent catalyst for Ullmann coupling reactions of phenols and nitro-substituted aryl halides. Mesoporous LaAlPO-5 has an excellent stability and recyclability in the Ullmann coupling of p-X-nitrobenzene (X=Cl, Br, and I) with 2-naphthol. These results are important in the exploration of attractive Ullmann coupling reactions and in the development of mesoporous zeolite catalysts for other organic reactions.
- Ke, Qingping,Wu, Mingzhou,Wang, Chao,Lu, Guanzhong
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p. 1557 - 1563
(2016/05/02)
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- Heterogeneous O -arylation of nitroarenes with substituted phenols over a copper immobilized mesoporous silica catalyst
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Highly porous and robust mesoporous silica, SBA-15 has been subjected to post-synthesis modification for the anchoring of copper through Schiff base moiety formation using the silicon alkoxide route. The hybrid porous material has been fully characterized by powder-XRD, electronic spectra, EPR, thermogravimetric analysis, N2 sorption measurements, and TEM and SEM/EDS studies. The efficiency of the catalyst has been assessed in the O-arylation reaction using various substituted phenols and nitroarenes in heterogeneous conditions. The catalytic coupling reaction efficiently produces unsymmetrical diaryl ethers. The impressive capability to activate substrates having electron-donating or electron-withdrawing substituents and to have a high turnover frequency in the catalytic reactions made the catalyst highly desirable.
- Maity, Tanmoy,Bhunia, Susmita,Das, Soma,Koner, Subratanath
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p. 33380 - 33386
(2016/05/09)
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- CsF/clinoptilolite: An efficient solid base in SNAr and copper-catalyzed Ullmann reactions
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CsF/clinoptilolite was found to be an efficient solid base catalyst for both SNAr and Ullmann ether reactions. A general and efficient one-step procedure was developed for the synthesis of biaryl ethers via direct coupling of electron-deficient aryl halides to phenols using CsF/clinoptilolite. The protocol was also applied to electron-rich aryl halides by addition of a catalytic amount of copper oxide nanoparticles. Both SNAr and Ullmann reactions were rapid and provided good to excellent yields.
- Keipour, Hoda,Hosseini, Abolfazl,Afsari, Amir,Oladee, Razieh,Khalilzadeh, Mohammad A.,Ollevier, Thierry
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- Synthesis and biological evaluation of pentanedioic acid derivatives as farnesyltransferase inhibitors
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Structure-based virtual screening of a commercial library identified pentanedioic acid derivatives (6 and 13b) as a kind of novel scaffold farnesyltransferase inhibitors (FTIs). Chemical modifications of the lead compounds, biological assays and analysis of the structure-activity relationships (SAR) were conducted to discover more potent FTIs. Some of them displayed excellent inhibition against FTase, and among them, the most active compound 13n with an IC50 value of 0.0029 μM and SAR analysis might be helpful to the discovery of more potent FTIs. This journal is
- Yang, Liuqing,Liu, Wei,Mei, Hanbing,Zhang, Yuan,Yu, Xiaojuan,Xu, Yufang,Li, Honglin,Huang, Jin,Zhao, Zhenjiang
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supporting information
p. 671 - 676
(2015/04/27)
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- Microwave assisted synthesis of selected diaryl ethers under Cu(I)-catalysis
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A practical synthesis of diaryl ethers has been achieved from cross coupling reaction between aryl halides and phenols under Cu(I)-catalysis and using ACHN as a ligand. The presence of catalysis and microwave-assistance benefitted the synthesis by increasing the yield of diaryl ethers with a reduction of reaction time.
- Navarro, Lorena,Pujol, M. Dolors
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supporting information
p. 1812 - 1815
(2015/03/30)
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- Ultrasound synthesis of diaryl ethers
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2,2-Bis[4-(4-nitroaryl)phenyl]hexafluoropropanes appropriate for the synthesis of monomers were prepared by the reaction of 2,2-bis[4-hydroxyphenyl)hexafluoropropane with 1-chloro-4-nitrobenzenes under ultrasonic activation.
- Begunov,Valyaeva,Belyaev,Dobretsova
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p. 1971 - 1974
(2016/05/11)
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- Barberry fruit extract assisted in situ green synthesis of Cu nanoparticles supported on a reduced graphene oxide-Fe3O4 nanocomposite as a magnetically separable and reusable catalyst for the O-arylation of phenols with aryl halides under ligand-free conditions
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In situ synthesis of copper nanoparticles (NPs) supported on a reduced graphene oxide (RGO)-Fe3O4 nanocomposite was carried out with barberry fruit extract as a reducing and stabilizing agent. The morphology and structure of the Cu/RGO-Fe3O4 nanocomposite was fully characterized by means of X-ray diffraction (XRD), Fourier transformed infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM), Raman, energy dispersive X-ray spectroscopy (EDS) and transmission electron microscopy (TEM). Cu/RGO-Fe3O4 was a promising catalyst for the O-arylation of phenols with aryl halides under ligand-free conditions. A diverse range of diaryl ethers were obtained in a good to high yield. Furthermore, due to the magnetic separability and high stability of the composite the catalyst could be separated conveniently from the reaction mixtures by an external permanent magnet and recycled multiple times without loss of catalytic activity.
- Nasrollahzadeh, Mahmoud,Maham, Mehdi,Rostami-Vartooni, Akbar,Bagherzadeh, Mojtaba,Sajadi, S. Mohammad
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p. 64769 - 64780
(2015/08/18)
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- A family of ligand and anion dependent structurally diverse Cu(II) Schiff-base complexes and their catalytic efficacy in an O-arylation reaction in ethanolic media
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Two nitrato bridged dinuclear systems [Cu2(L1)2(NO3)3]NO3·H2O (1) and [Cu2(L2)2(NO3)3]NO3·MeOH (2), five monomeric complexes viz. [Cu(L3)(NO3)]NO3 (3), [Cu(L4)(NO3)]NO3 (4), [Cu(L5)(NO3)]NO3 (5), [Cu(L6)(NO3)NO3] (7), [Cu(L7)(NO3)]NO3 (8) and one hetero bi-bridged (phenoxido and water) dinuclear complex [Cu2(L2)2(H2O)2](ClO4)4·4H2O (6) have been synthesized and characterized using several physicochemical methods (L1 = 1-(N-3-methoxysalicylideneimino)-ethane-2-piperazine, L2 = 1-(N-3-ethoxysalicylideneimino)-ethane-2-piperazine, L3 = 1-(N-4′-ethoxy-α-methylasalicylideneimino)-ethane-2-piperazine, L4 = 1-(N-5′-chloro-α-methylasalicylideneimino)-ethane-2-piperazine, L5 = 1-(N-5-chlorosalicylideneimino)-ethane-2-piperazine, L6 = 1-(N-4-methoxysalicylideneimino)-ethane-2-piperazine and L7 = 1-(N-4′-methoxy-α-methylasalicylideneimino)-ethane-2-piperazine). X-ray structural analysis showed that complexes 1 and 2 are discrete dinuclear species where the pentacoordinated metal centers are bridged through a nitrate ion. In 3, 4, 5 and 8 the monomeric copper center displays a square pyramidal geometry with a weak axial Cu-O bond. In 7, the monomeric copper center shows a distorted octahedral geometry with two coordinated nitrate anions. However, in 6 the two copper centers coordinate in different manners (one is square-pyramidal and the other is distorted octahedral) and are bridged through a phenoxido group and a water molecule. All complexes efficiently catalyze the C-O coupling reaction under homogeneous conditions at 80 °C to afford unsymmetrical diaryl ethers using nitroarenes to act as an excellent electrophile. Notably, the reaction is carried out in ethanol media which facilitates the avoidance of toxic wastes. Structurally diverse copper(ii) Schiff-base complexes have rarely been used systematically in catalytic C-O coupling reactions.
- Maity, Tanmoy,Saha, Debraj,Bhunia, Susmita,Brand?o, Paula,Das, Soma,Koner, Subratanath
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p. 82179 - 82191
(2015/10/12)
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- A highly active and recyclable catalyst for the synthesis of indole and phenyl ether
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A new simple catalytic system consisting of copper-aluminium and hydrotalcite (CuAl-HT) has been developed using a facile one-pot method without harm to the environment. The catalyst was characterized using TEM, XRD and XPS. It could be used as an efficient catalyst for the synthesis of both indole and phenyl ether. As expected, the catalyst afforded high catalytic activity for the selective synthesis of indole via intramolecular dehydrogenative N-heterocyclization of 2-(2-aminophenyl)ethanol. Meanwhile, it also exhibited superior catalytic properties for an Ullmann-type coupling reaction to synthesise phenyl ether from iodobenzene and phenol. The CuAl-HT catalyst showed higher activity than conventional catalysts based on copper and could be recycled several times with stable catalytic activity. This procedure has real economic advantages since no expensive materials were used.
- Qiao, Bo,Zhang, Le,Li, Rong
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p. 93463 - 93469
(2015/11/17)
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- Maghemite-Copper Nanocomposites: Applications for Ligand-Free Cross-Coupling (C-O, C-S, and C-N) Reactions
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A magnetically retrievable, efficient, and benign maghemite-Cu nanocatalyst was synthesized from inexpensive precursors and applied for C-O, C-N, and C-S bond-formation reactions. The obtained maghemite-Cu nanocatalyst was characterized by various techniques such as XRD, X-ray photoelectron spectroscopy, field-emission gun SEM with energy-dispersive spectroscopy, atomic absorption spectroscopy, TEM, high-angle annular dark-field scanning transmission electron microscopy, FTIR spectroscopy, and M?ssbauer spectroscopy. Excellent catalytic activity, ease of recovery, and reusability without a significant loss of yield make the present protocol highly sustainable to deal with industrial and environmental concerns. Magnetic attraction: A magnetically retrievable, efficient, and benign maghemite-Cu nanocatalyst is synthesized from inexpensive precursors and applied for C-O, C-N, and C-S bond-formation reactions. Excellent catalytic activity, ease of recovery, and reusability without significant loss of yield make the present protocol highly sustainable to deal with industrial and environmental concerns.
- Sharma, Rakesh K.,Gaur, Rashmi,Yadav, Manavi,Rathi, Anuj K.,Pechousek, Jiri,Petr, Martin,Zboril, Radek,Gawande, Manoj B.
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p. 3495 - 3502
(2015/11/10)
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- Ligand free copper-catalyzed heterogeneous O-arylation reaction under green condition
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A highly porous Zn-based iso-reticular metal-organic framework (IRMOF-3) has been selected for covalent modification. Pyridine-2-aldehyde has been used to decorate the free amine group of IRMOF-3 in the porous matrix. Schiff base moiety thus generated has been availed to anchor copper(II) ions to prepare the desired catalyst that catalyzes O-arylation reactions heterogeneously under mild reaction conditions. Porous catalyst demonstrates size selectivity in products when various substrates undergo O-arylation with α and β-naphthol.
- Maity, Tanmoy,Saha, Debraj,Das, Soma,Bhunia, Susmita,Koner, Subratanath
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p. 141 - 148
(2014/12/10)
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- Palladium(II) thiosemicarbazone complex: Synthesis, structure and application to carbon-oxygen cross-coupling reaction
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A simple route for the synthesis of square-planar palladium(II) 3-methyl-thiophene-2-aldehyde thiosemicarbazone complex is described. The composition of the complex has been established by elemental analysis and spectral methods. The molecular structure was confirmed by single crystal X-ray diffraction study. Further, the complex was used as a potential catalyst for the carbon-oxygen cross-coupling reaction of activating, non-activating and deactivating aryl iodides or aryl bromides with p-cresol.
- Suganthy, Pandimuni Kalpaga,Prabhu, Rupesh Narayana,Sridevi, Venugopal Shanmugham
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- Synthesis and properties of 1,3,4-oxadiazole-containing bismaleimides with asymmetric structure and the copolymerized systems thereof with 4,4′-bismaleimidodiphenylmethane
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Two novel bismaleimide monomers containing 1,3,4-oxadiazole and asymmetric structure, i.e., 2-[4-(4-maleimidophenoxy)phenyl]-5-(4-maleimidophenyl)-1,3,4- oxadiazole (p-Mioxd) and 2-[3-(4-maleimidophenoxy)phenyl]-5-(4-maleimidophenyl)- 1,3,4-oxadiazole (m-Mioxd), were designed and synthesized. The chemical structures of the monomers were confirmed using Fourier transform infrared spectroscopy (FTIR), 1H NMR and 13C NMR spectroscopy and elemental analysis. The thermal properties of the monomers were investigated by differential scanning calorimetry (DSC) and thermogravimetric analysis (TGA). The results indicate that the incorporation of the 1,3,4-oxadiazole and asymmetric structure could improve the solubility and processability of the BMI monomers and the thermal stability of the resins. Composites composed of glass cloth and 4,4′-bismaleimidodiphenylmethane (BMDM), which were modified with 2.5, 5 and 10 wt% p-Mioxd and m-Mioxd, respectively, were also prepared. The TGA and DMA results demonstrate that the resulting composites have excellent thermal stability with high residual weight percentage at 700 °C (>45%) and Tg (>450 °C).
- Xia, Lianlian,Zhai, Xuejiao,Xiong, Xuhai,Chen, Ping
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p. 4646 - 4655
(2014/01/17)
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- Synthesis and biological evaluation of novel thiadiazole amides as potent Cdc25B and PTP1B inhibitors
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A series of novel thiadiazole amide derivatives have been synthesized and evaluated for inhibitory activities against Cdc25B and PTP1B. Most of them showed inhibitory activities against Cdc25B (IC50 = 1.18-8.01 μg/mL) and PTP1B (IC50 = 0.85-8.75 μg/mL), respectively. Moreover, compounds 5b and 4l were most potent with IC50 values of 1.18 and 0.85 μg/mL for Cdc25B and PTP1B, respectively, compared with reference drugs Na3VO4 (IC50 = 0.93 μg/mL) and oleanolic acid (IC50 = 0.85 μg/mL). The results of selectivity experiments showed that the target compounds were selective inhibitors against PTP1B and Cdc25B. Enzyme kinetic experiments demonstrated that compound 5k was a specific inhibitor with the typical characteristics of a mixed inhibitor.
- Li, Yingjun,Yu, Yang,Jin, Kun,Gao, Lixin,Luo, Tongchuan,Sheng, Li,Shao, Xin,Li, Jia
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p. 4125 - 4128
(2014/09/29)
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- Palladium nanoparticles supported on natural nanozeolite clinoptilolite as a catalyst for ligand and copper-free C-C and C-O cross coupling reactions in aqueous medium
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In this article, Pd0-nanoparticles supported on natural nanozeolite clinoptilolite (CP) were successfully synthesized, and the catalytic activity of the nanocatalyst was investigated in C-C and C-O coupling reactions, namely the Sonogashira and Ullmann condensation reactions in an aqueous medium. The nanocatalyst was characterized by various techniques such as powder-XRD, BET, SEM, TEM, HRTEM, TEM-EDS, ICP-OES and XPS. From an electron microscopy (SEM) study it can be inferred that the particles are mostly spherical or of ellipsoidal shape and have diameters ranging from 25 to 80 nm. A HRTEM study reveals that Pd0-nanoparticles supported on nanozeolite CP have an average diameter of ~10 nm. The supported palladium nanoparticles showed excellent catalytic activity in the synthesis of aryl alkynes and diaryl ethers in high yields. In addition, the nanocatalyst could be recycled and reused several times without significant loss of catalytic activity.
- Baghbanian, Seyed Meysam,Yadollahy, Horieh,Tajbakhsh, Mahmood,Farhang, Maryam,Biparva, Pourya
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p. 62532 - 62543
(2015/02/19)
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- Coupling of boronic acids with amines in the presence of a supported copper catalyst
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An efficient heterogeneous catalytic method was developed for Chan-Lam reaction, coupling of amines and boronic acid. Copper on 4 A molecular sieve provided yields comparable to the methods published. The method provides the main advantages of a heterogeneous catalytic procedure, the preparation of the catalyst is easy, the workup of the reaction mixture is simple. Graphical abstract: [Figure not available: see fulltext.]
- Debreczeni, Nora,Fodor, Anna,Hell, Zoltan
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p. 1547 - 1551,5
(2014/11/12)
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- Impregnated copper on magnetite as catalyst for the O-arylation of phenols with aryl halides
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Nanoparticle Fe3O4 encapsulated CuO, as a heterogeneous catalyst, is a facile system for the synthesis of diaryl ethers by the cross-coupling reaction of various substituted aryl halides with various substituted phenols, which avoids using any type of expensive ligand and can be recovered from the reaction mixture by using a simple magnet. Moreover, this catalyst can be reused three times with high catalytic activity.
- Zhang, Ying-Peng,Shi, Ai-Hong,Yang, Yun-Shang,Li, Chun-Lei
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p. 141 - 145
(2014/02/14)
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- Palladium nanoparticles supported on silica diphenylphosphinite as efficient catalyst for C-O and C-S arylation of aryl halides
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Silica diphenylphosphinite (SDPP) can be easily obtained through direct phosphorylation of silica gel. Further reaction of SDPP with Pd(II) produces nano Pd(0)/SDPP. This nano Pd(0) catalyst exhibits excellent reactivity for the C-O and C-S arylation of different aryl iodides, bromides and chloride with phenols and thiophenols. This heterogeneous catalyst shows excellent recyclability and can be easily recovered and reused for several runs. Copyright
- Iranpoor, Nasser,Firouzabadi, Habib,Rostami, Abed
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p. 501 - 506
(2013/09/23)
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- Facile preparation of unsymmetrical diaryl ethers from unsymmetrical diaryliodonium tosylates and phenols with high regioselectivity
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Unsymmetrical diaryl ethers were efficiently obtained in good yields by the reactions of aryl(4-methoxyphenyl)iodonium tosylates with phenols, and aryl(2,4-dimethoxyphenyl)iodonium tosylates with phenols, in the presence of potassium carbonate in acetonitrile, respectively. The latter iodonium tosylates provided the corresponding unsymmetrical diaryl ethers in good yields with high regioselectivities, together with the quantitative formation of 1-iodo-2,4-dimethoxybenzene. Georg Thieme Verlag Stuttgart New York.
- Kakinuma, Yohji,Moriyama, Katsuhiko,Togo, Hideo
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p. 183 - 188
(2013/02/23)
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- First palladium-catalyzed denitrated coupling reaction of nitroarenes with phenols
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The first palladium-catalyzed protocol for the denitrated coupling reaction of nitroarenes with phenols has been developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. The cyclopalladated ferrocenylimine (catalyst Ic) exhibited highly catalytic activity for this transformation with low catalyst loading (0.75 mol%) and short reaction time (2 h). The efficiency of this reaction was demonstrated by its compatibility with a range of groups. Moreover, the rigorous exclusion of air or moisture was not required in these transformations. Copyright
- Wang, Hailei,Yu, Ajuan,Cao, Aijuan,Chang, Junbiao,Wu, Yangjie
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p. 611 - 614
(2013/10/21)
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- Ligand-free solid supported palladium(0) nano/microparticles promoted C-O, C-S, and C-N cross coupling reaction
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Ligand-free solid-supported nano and microparticles of Pd(0) (SS-Pd) were used as a heterogeneous catalyst in carbon-heteroatom bond formation reactions. Nitro substituted aryl halides reacted with oxygen, sulfur, and nitrogen nucleophiles to afford the corresponding products in good yields. A one-pot sequential cross coupling and nitro-reduction was also performed using the same SS-Pd catalyst to access amine substituted carbon-heteroatomic molecules. In addition, SS-Pd could be recycled up to seven runs without a significant loss of catalytic activity.
- Bandna,Guha, Nitul Ranjan,Shil, Arun K.,Sharma, Dharminder,Das, Pralay
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supporting information
p. 5318 - 5322
(2012/10/30)
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- Ligand-free copper-catalyzed O-arylation of nitroarenes with phenols
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The first example of ligand-free copper-catalyzed O-arylation of nitroarenes with phenols was developed, achieving unsymmetrical diaryl ethers in moderate to excellent yields. This arylation proceeded smoothly without promotion of the ligands, and displayed great functional group compatibility. Thus, the method represents a new, facile, and cost-effective approach to access unsymmetrical diaryl ethers.
- Chen, Jiuxi,Wang, Xingyong,Zheng, Xingwang,Ding, Jinchang,Liu, Miaochang,Wu, Huayue
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supporting information
p. 8905 - 8907
(2012/10/29)
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- Potassium fluoride supported on natural nanoporous zeolite: A new solid base for the synthesis of diaryl ethers
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An efficient and inexpensive synthesis of diaryl ethers has been developed. The process involves the nucleophilic aromatic substitution of electron-deficient aryl halides and phenols and is mediated by potassium fluoride/Clinoptilolite (KF/CP) in dimethyl sulfoxide (DMSO). The approach affords good to excellent yields of the arylated products without the need for additional cation capture. The solid base is also efficient in the Ullmann ether synthesis. A new, inexpensive solid base for the synthesis of diaryl ethers has been developed. Clinoptilolite, a natural zeolite with a high tendency for cation capture, combined with potassium fluoride, provides an efficientsolid base for the deprotonation of phenols in nucleophilic reactions. The same solid base acts as a reliable base for the copper-catalyzed synthesis of diaryl ethers. Copyright
- Khalilzadeh, Mohammad A.,Hosseini, Abolfazl,Pilevar, Afsaneh
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experimental part
p. 1587 - 1592
(2011/04/22)
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- Discovery of potent and selective thienopyrimidine inhibitors of Aurora kinases
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In an effort to discover Aurora kinase inhibitors, an HTS hit revealed an amide containing pyrrolopyrimidine compound. Replacement of the pyrrolopyrimidine residue with a thienopyrimidine moiety led to a series of potent and selective Aurora inhibitors.
- McClellan, William J.,Dai, Yujia,Abad-Zapatero, Cele,Albert, Daniel H.,Bouska, Jennifer J.,Glaser, Keith B.,Magoc, Terry J.,Marcotte, Patrick A.,Osterling, Donald J.,Stewart, Kent D.,Davidsen, Steven K.,Michaelides, Michael R.
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scheme or table
p. 5620 - 5624
(2011/10/12)
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- Bis(μ-iodo)bis[(-)-sparteine]-dicopper: A versatile catalyst for direct O-Arylation and O-Alkylation of phenols and aliphatic alcohols with haloarenes
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The easy to prepare dimeric bis(μ-iodo)bis[(-)-sparteine]- dicopper ([CuI{(-)-spa}]2 complex) is shown to be versatile catalyst for O-arylation and O-alkylation with various aryl halides with phenols and aliphatic alcohols respectively, including less reactive aryl chlorides, such as chlorobenzene under mild conditions.
- Satyanarayana, Ponnam,Maheswaran, Hariharasarma,Kantam, Mannepalli Lakshmi,Bhargava, Suresh
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supporting information; experimental part
p. 788 - 790
(2011/08/22)
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- Nano ceria catalyzed Ullmann type coupling reactions
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Ullmann type intermolecular coupling of aryl halide with hetero-aromatic compounds, such as phenols, amines, and thiophenols are key reactions for the formation of carbon-heteroatom bond in organic synthesis. We report a robust and novel method that provides an efficient and economic route for the synthesis of O, N, and S-arylation via Ullman coupling by using nano cerium oxide (ceria, CeO2). CeO2 is a cheaper catalyst compared to related copper based catalysts. This method provides a wide range of substrate applicability in the case of phenols and amines. Less reactive chlorobenzene substituted with strong electron withdrawing groups such as 4-nitrochlorobenzene and 4-cyanochlorobenzene favor the reaction. This protocol avoids the use of ligand and gives arylated product in satisfactory yields.
- Agawane, Sandeep M.,Nagarkar, Jayashree M.
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experimental part
p. 5220 - 5223
(2011/10/12)
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- Cross-coupling reactions of aryl halides with amines, phenols, and thiols catalyzed by an N,N′-dioxide-copper(I) catalytic system
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The coupling reactions of various N, O, and S nucleophilic reagents with aryl halides have been successfully carried out under mild conditions by using a novel chiral N,N′-dioxide-copper(I) catalytic system as the catalyst. This versatile and efficient catalyst system has been demonstrated to facilitate the cross-coupling reactions of aryl halides with amines, phenols, and thiols to afford the corresponding desired products in good to excellent yields.
- Yang, Haitao,Xi, Chao,Miao, Zhiwei,Chen, Ruyu
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supporting information; experimental part
p. 3353 - 3360
(2011/08/03)
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- A PEG1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system that regulates homogeneously catalyzed C-O coupling of organic halides with phenols and alcohols under ligand-free conditions
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An efficient, experimentally simple, and convenient procedure for the C-O coupling of organic halides with phenols and alcohols in a PEG 1000-DAIL[CdCl3]-toluene temperature-dependent biphasic system has been developed. The product can be easily isolated by a simple decantation, and the catalytic system can be recycled and reused without loss of catalytic activity.
- Hu, Yu Lin,Ma, Xiao Yun,Lu, Ming
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experimental part
p. 471 - 480
(2011/06/22)
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- Copper(I)-catalyzed C-C and C-O coupling reactions using hydrazone ligands
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Copper-catalyzed C-C coupling reaction of aryl iodides with diethylmalonate in toluene at 90C gave arylated malonates using 5 mol% of CuI with hydrazone 1a as a ligand in good yields under an aerobic atmosphere. We also found CuI/hydrazone 1b in toluene to be an efficient catalytic system for C-O coupling reactions of aryl bromides with phenols to give aryl ethers in good yields at 110C under an aerobic atmosphere.
- Mino, Takashi,Yagishita, Fumitoshi,Shibuya, Masanori,Kajiwara, Kenji,Shindo, Hiroaki,Sakamoto, Masami,Fujita, Tsutomu
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experimental part
p. 2457 - 2460
(2010/01/07)
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- Synthesis and structure of 1-chlorosulfonyl-2-(4′-nitrophenoxy)-5- methylbenzene
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Diphenyl ethers are structural elements found in medicinally useful antibiotics such as vancomycin as well as in biological toxins in the environment such as dioxins. The purpose of this paper is to report the synthesis and characterization of the previously unreported 1-chlorosulfonyl-2- (4′-nitrophenoxy)-5-methylbenzene, a trisubstituted diphenyl ether derivative. 1H NMR (CDCl3) δ 2.45 (3H, methyl 5, s), 7.07 (1H, H4, d, J ~8.27 Hz), 7.13 (2H, H 2′, H6′, d, J ~9.0 Hz), 7.54 (1H, H 3, d, J ~8.28 Hz), 7.87 (1H, H6, s), 8.22 (2H, H 3′, H5′, J ~9 Hz); 13C NMR (CDCl3) δ 20.7, 118.2, 121.9, 126.0, 129.8, 135.2, 135.8, 137.8, 143.8, 150.3, 161.4. An X-ray analysis has provided valuable insight into the effect of steric factors on the three dimensional shape of this compound which serves as a useful advanced intermediate in the synthesis of these biologically active molecules. A multistep synthesis of this molecule has been designed by retrosynthetic analysis as part of an ongoing program aimed at a function-oriented, multi-step economical synthesis of vancomycin lead antibiotics. Crystals are triclinic, space group P-1, a = 7.6537(15), b = 8.976(2), c = 11.050(2) A, α = 67.645(11), β = 79.735(11), γ = 87.798(10)°, V = 690.5(2) A3, Z = 2.
- Silveira, Michael H.,Fronczek, Frank R.
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scheme or table
p. 504 - 509
(2010/04/24)
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- Synthesis of glutamic acid analogs as potent inhibitors of leukotriene A4 hydrolase
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Leukotriene B4 (LTB4) is a potent pro-inflammatory mediator that has been implicated in the pathogenesis of multiple diseases, including psoriasis, inflammatory bowel disease, multiple sclerosis and asthma. As a method to decrease the level of LTB4 and possibly identify novel treatments, inhibitors of the LTB4 biosynthetic enzyme, leukotriene A4 hydrolase (LTA4-h), have been explored. Here we describe the discovery of a potent inhibitor of LTA4-h, arylamide of glutamic acid 4f, starting from the corresponding glycinamide 2. Analogs of 4f are then described, focusing on compounds that are both active and stable in whole blood. This effort culminated in the identification of amino alcohol 12a and amino ester 6b which meet these criteria.
- Kirkland, Thomas A.,Adler, Marc,Bauman, John G.,Chen, Ming,Haeggstroem, Jesper Z.,King, Beverly,Kochanny, Monica J.,Liang, Amy M.,Mendoza, Lisa,Phillips, Gary B.,Thunnissen, Marjolein,Trinh, Lan,Whitlow, Marc,Ye, Bin,Ye, Hong,Parkinson, John,Guilford, William J.
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p. 4963 - 4983
(2008/12/21)
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- Palladium N-heterocyclic carbene catalysts for synthesis of diaryl ethers
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Novel functionalized 1,3-dialkylimidazolinium (LH) salts as precursors for N-heterocyclic carbenes (NHCs) have been prepared and successfully applied in the palladium-catalyzed synthesis of diaryl ethers and arylation of benzaldehydes. An efficient cataly
- Akko?, Mitat,Gürbüz, Nevin,?etinkaya, Engin,?zdemir, Ismail
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experimental part
p. 1781 - 1784
(2009/04/11)
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- Copper-catalyzed Ullmann coupling under ligand- and additive- free conditions. Part 1: O-Arylation of phenols with aryl halides
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O-Arylation of a wide variety of substituted phenols and aliphatic alcohols with aryl halides catalyzed by copper iodide under mild ligand and additive free conditions (nBu4NBr, DMF, K3PO4, reflux, 22 h) is accomplished in good to excellent product yields (up to 95%).
- Chang, Joyce Wei Wei,Chee, Sheena,Mak, Shiya,Buranaprasertsuk, Pongchart,Chavasiri, Warinthorn,Chan, Philip Wai Hong
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p. 2018 - 2022
(2008/09/19)
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- Immobilization of copper in organic-inorganic hybrid materials: a highly efficient and reusable catalyst for the Ullmann diaryl etherification
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The immobilization of copper in organic-inorganic hybrid materials catalyzing the Ullmann reaction has been described. Phenols reacted with aryl iodides, aryl bromides and aryl chlorides smoothly in the presence of a 3-(2-aminoethylamino)propyl functionalized silica gel immobilized copper catalyst. The protocol involved the use of DMSO as the solvent, and potassium fluoride as the base. The reactions generated the corresponding cross-coupling products in good to excellent yields. Furthermore, the silica-supported copper could be recovered and recycled by a simple filtration of the reaction solution and used for 10 consecutive trials without loss of its reactivity.
- Miao, Tao,Wang, Lei
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- Correlation between molecular dipole moment and centrosymmetry in some crystalline diphenyl ethers
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The presence of a large molecular dipole moment in diphenyl ethers leads unequivocally to a centrosymmetric crystal structure. The Royal Society of Chemistry 2005.
- Dey, Archan,Desiraju, Gautam R.
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p. 2486 - 2488
(2007/10/03)
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- Neutral alumina-K2CO3: An eco-friendly system for synthesis of diaryl ethers under microwave irradiation
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Electron deficient halo benzenes undergo smoothly direct condensation with a wide range of phenols under microwave irradiation using neutral alumina as solid support to yield biaryl ethers in excellent yields.
- Narsaiah, A. Venkat,Nagaiah
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p. 2478 - 2481
(2007/10/03)
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- A general and efficient protocol for the synthesis of biaryl ethers from aryl silyl ethers using Cs2CO3
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A general and efficient one-step procedure has been developed for the synthesis of biaryl ethers via direct coupling of electron-deficient arylhalides or aryl triflates to aryl t-butyldimethylsilyl (TBS) ethers using Cs 2CO3. The protocol was also applied to electron-rich arylhalides by addition of a catalytic amount of copper(I) iodide. The reaction is rapid and provides good to excellent yields.
- Cui, Sun-Liang,Jiang, Zhi-Yong,Wang, Yan-Guang
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p. 1829 - 1831
(2007/10/03)
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- Microwave assisted aromatic nucleophilic substitution reaction under solventless condition
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We report here microwave assisted aromatic nucleophilic substitution reaction of 1-chloro-4-nitrobenzene with different phenoxides.
- Rebeiro, Geeta L.,Khadilkar, Bhushan M.
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p. 1405 - 1410
(2007/10/03)
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- Synthesis of polymeric diaryliodonium salts and its use in preparation of diaryl sulfides and diaryl ethers
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Polymeric diaryliodonium salts were synthesized and applied to the preparation of diaryl ethers and diaryl sulfides under mild conditions. The byproduct, polyiodostyrene, could be recycled and reused.
- Huang,Zhu,Xu
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p. 2823 - 2828
(2007/10/03)
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- Synthesis of diaryl ethers using an easy-to-prepare, air-stable, soluble copper(I) catalyst
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We have found that bromo(triphenylphosphine)copper(I), an air-stable and soluble copper(I) complex, can be used as a catalyst in the synthesis of diaryl ethers. Using this catalyst, we have synthesized diaryl ethers from electron-rich aryl bromides and electron-rich phenols in the presence of cesium carbonate, in 17-24 h, in NMP. We also found that electron-deficient aryl bromides couple with phenols in the presence of cesium carbonate, in 6 h in NMP at 70°C, without the catalyst.
- Gujadhur,Venkataraman
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p. 2865 - 2879
(2007/10/03)
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