- Thermally stable and robust gadolinium-based metal-organic framework: Synthesis, structure and heterogeneous catalytic O-arylation reaction
-
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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- A novel magnetic polyacrylonotrile-based palladium Core?Shell complex: A highly efficientcatalyst for Synthesis of Diaryl ethers
-
The present article describes the synthesis of a new magnetic polyacrylonitrile-based Pd catalyst involving polyacrylonitrile modified via 2-aminopyridine as an efficient support to immobilize Pd nanoparticles. The simple reusability, easy separation and high stability of this Pd complex make it an excellent candidate to generate a C–O bond via Ph-X activation which is a really important subject in achieving biologically active compounds. It is worth to note access to good and high yields as well as broad substrate scope have resulted from superior reactivity of this catalyst complex. Furthermore, the structure of the magnetic polyacrylonitrile-based heterogeneous catalyst was characterized by fourier transmission infrared (FT-IR) spectroscopy, field emission scanning electron microscopy (FE-SEM) and transmission electron microscopy (TEM), X-ray diffraction (XRD). Also, its thermal properties were studied by thermogravimetric analysis (TGA).
- Eslami, Mohammad,Jarahiyan, Atefeh,Moghaddam, Firouz Matloubi,Pourjavadi, Ali
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- A new strategy to design a graphene oxide supported palladium complex as a new heterogeneous nanocatalyst and application in carbon–carbon and carbon-heteroatom cross-coupling reactions
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The palladium nanoparticles were successfully stabilized with an average diameter of 6–7?nm through the coordination of palladium and terpyridine-based ligands grafted on graphene oxide surface. The graphene oxide supported palladium nanoparticles were thoroughly characterized and applied as an efficient heterogeneous catalyst in carbon–carbon (Suzuki-Miyaura, Mizoroki-Heck coupling reactions) and carbon–heteroatom (C-N and C-O) bond-forming reactions. The catalyst was simply recycled from the reaction mixture and was reused consecutive four times with small drop in catalytic activity.
- Bahrami, Kiumars,Targhan, Homa
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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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- Design of BNPs-TAPC Palladium Complex as a Reusable Heterogeneous Nanocatalyst for the O-Arylation of Phenols and N-Arylation of Amines
-
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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- 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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- Overcoming solid handling issues in continuous flow substitution reactions through ionic liquid formation
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Substitutions such as acylations, arylations, and alkylations are some of the most commonly run reactions for building complex molecules. However, the requirement of a stoichiometric base to scavange acid by-products creates significant challenges when operating in continuous flow due to solid handling issues associated with precipitating base·HX salts. We present a general and simple strategy to overcome these solid handling issues through the use of acid scavenging organic bases that generate low- to moderate-melting ionic liquids upon protonation. The application of these bases towards the most commonly run substitutions are demonstrated, enabling reactions to be run in flow without requiring additional equipment, specific solvents, or dilute reaction conditions to prevent clogging.
- Kashani, Saeed,Sullivan, Ryan J.,Andersen, Mads,Newman, Stephen G.
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supporting information
p. 1748 - 1753
(2018/04/30)
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- COMPOSITIONS AND METHODS FOR INHIBITING RETICULON 4
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Disclosed herein, inter alia, are compositions and methods useful for inhibiting reticulon 4(RTN4).
- -
-
Paragraph 0726
(2018/08/26)
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- N-Picolinamides as ligands in Ullman type C–O coupling reactions
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Copper-catalyzed modified Ullmann coupling reactions creating C–O bonds, including diaryl ethers or phenols, are vital to organic synthesis. Synthesized N-phenyl-2-pyridinecarboxamide and its derivatives were used as ligands in conjunction with catalytic copper sources in the formation of various diaryl ethers and phenols. Various aryl and heteroaryl halides with electron donating and withdrawing groups were reacted with various phenols under mild reaction conditions providing moderate to excellent yields.
- Damkaci, Fehmi,Sigindere, Cihad,Sobiech, Thomas,Vik, Erik,Malone, Joshua
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p. 3559 - 3564
(2017/10/05)
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- Chemoproteomics-enabled covalent ligand screen reveals a cysteine hotspot in reticulon 4 that impairs ER morphology and cancer pathogenicity
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Chemical genetics has arisen as a powerful approach for identifying novel anti-cancer agents. However, a major bottleneck of this approach is identifying the targets of lead compounds that arise from screens. Here, we coupled the synthesis and screening of fragment-based cysteine-reactive covalent ligands with activity-based protein profiling (ABPP) chemoproteomic approaches to identify compounds that impair colorectal cancer pathogenicity and map the druggable hotspots targeted by these hits. Through this coupled approach, we discovered a cysteine-reactive acrylamide DKM 3-30 that significantly impaired colorectal cancer cell pathogenicity through targeting C1101 on reticulon 4 (RTN4). While little is known about the role of RTN4 in colorectal cancer, this protein has been established as a critical mediator of endoplasmic reticulum tubular network formation. We show here that covalent modification of C1101 on RTN4 by DKM 3-30 or genetic knockdown of RTN4 impairs endoplasmic reticulum and nuclear envelope morphology as well as colorectal cancer pathogenicity. We thus put forth RTN4 as a potential novel colorectal cancer therapeutic target and reveal a unique druggable hotspot within RTN4 that can be targeted by covalent ligands to impair colorectal cancer pathogenicity. Our results underscore the utility of coupling the screening of fragment-based covalent ligands with isoTOP-ABPP platforms for mining the proteome for novel druggable nodes that can be targeted for cancer therapy.
- Bateman,Nguyen,Roberts,Miyamoto,Ku,Huffman,Petri,Heslin,Contreras,Skibola,Olzmann,Nomura
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supporting information
p. 7234 - 7237
(2017/07/11)
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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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- Para-Selective Cu-Catalyzed C-H Aryloxylation of Electron-Rich Arenes and Heteroarenes
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Cu-catalyzed reaction of phenols with electron-rich arene or heteroarene ligands of unsymmetrical diaryl-λ3-iodanes is a key step in the developed one-pot two-step method for intermolecular para-selective C-H aryloxylation of heteroarenes and arenes.
- Sokolovs, Igors,Suna, Edgars
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p. 371 - 379
(2016/01/25)
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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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- 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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- 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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- 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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- A highly active reusable polymer anchored copper catalyst for C-O, C-N and C-S cross coupling reactions
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A new furfural functionalized polymer-amine grafted with copper catalyst has been designed and employed for the N-arylation, O-arylation and S-arylation reactions under an open air condition to afford the corresponding coupled products in good to excellent yields. This solid supported catalyst was characterized by Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), UV-vis spectroscopy and scanning electron microscope (SEM). The developed catalyst can be facilely recovered and reused five times without significant decrease in activity and selectivity. This result confirms that the polymer anchored complex was not leached during the reaction, suggesting the true heterogeneous nature of the catalyst.
- Islam, Sk.Manirul,Salam, Noor,Mondal, Paramita,Roy, Anupam Singha,Ghosh, Kajari,Tuhina
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- Synthesis and evaluation of new diaryl ether and quinoline hybrids as potential antiplasmodial and antimicrobial agents
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Synthesis and bioevaluation of new diaryl ether hybridized quinoline derivatives as antiplasmodial, antibacterial and antifungal agents is reported. It was encouraging to discover that several compounds displayed 2-3 folds better efficacy than chloroquine in chloroquine-resistant K1 strain of Plasmodium falciparum. Further, a few members of the library displayed good antibacterial efficacy against gram positive strains of bacteria but none of the compounds displayed any significant antifungal activity.
- Mishra, Amita,Batchu, Harikrishna,Srivastava, Kumkum,Singh, Pratiksha,Shukla, Pravin K.,Batra, Sanjay
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supporting information
p. 1719 - 1723
(2014/04/17)
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- Ligand-free Ullmann-type C-heteroatom couplings under practical conditions
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A new practical ligand-free protocol for copper-catalyzed C-heteroatom cross-coupling reactions (Ullmann-type) is described. The use of dimethyl sulfoxide (DMSO) as the solvent overcomes the need to use organic auxiliary ligands; thus, DMSO is revealed as a nontoxic and superior solvent for Ullmann-type coupling reactions. This method allows the arylation of a wide range of amides, alcohols, and amines under practical conditions with bromobenzene and iodobenzene derivatives and will likely find direct application in current organic synthesis. The competitive reactivity among different functional groups is reported and rationalized, and the possibility to achieve selective arylation reactions is demonstrated. Copyright
- Gueell, Imma,Ribas, Xavi
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p. 3188 - 3195
(2014/06/09)
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- Synthesis and biological evaluation of XB-1 analogues as novel histamine H3 receptor antagonists and neuroprotective agents
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A novel class of H3 receptor antagonists, XB-1 analogues based on benzophenone or oxydibenzene scaffolds were synthesized, and their biological activities were evaluated to determine their in vitro neuroprotective effects against Aβ25-35-induced damage in primary cortical neurons and against glutamate-induced neuronal injury in primary cerebellar granule neurons. The results indicated that all of the tested analogues displayed neuroprotective activity at 0.1 μM or 1 μM. These findings may provide new insights into the development of novel promising H3 receptor antagonists with potential neuroprotective activity.
- Bao, Xiaofeng,Jin, Yanyan,Liu, Xiaolu,Liao, Hong,Zhang, Luyong,Pang, Tao
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p. 6761 - 6775
(2014/02/14)
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- Room temperature Ullmann type C-O and C-S cross coupling of aryl halides with phenol/thiophenol catalyzed by CuO nanoparticles
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C-O/C-S cross coupling of aryl halides with phenol or thiophenol was studied under ligand-free condition at room temperature over CuO nanocatalyst. The scope of the reaction was extended to various aryl halides and substituted phenols under optimized condition. In general, efficient, selective, and reusable heterogeneous nano CuO catalytic system has been developed for room temperature C-O and C-S Ullmann type cross coupling reactions.
- Babu, S. Ganesh,Karvembu
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p. 1677 - 1680
(2013/03/28)
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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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- 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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- 2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide as a novel ligand for the copper-catalyzed coupling reaction of phenols and aryl halides
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2-Carbomethoxy-3-hydroxyquinoxaline-di-N-oxide was identified as an efficient novel ligand for the copper-catalyzed coupling of aryl halides with various phenols under mild conditions. The catalytic system shows great functional-group tolerance and excellent reactive selectivity.
- Qiu, Yatao,Jia, Weijun,Yao, Zhiyi,Wu, Fanhong,Jiang, Sheng
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p. 1502 - 1510
(2013/05/08)
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- Optimization of 5-hydroxytryptamines as dual function inhibitors targeting phospholipase A2 and leukotriene A4 hydrolase
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Dual function inhibitors targeting phospholipase A2 (PLA 2) and leukotriene A4 hydrolase (LTA4H) may balance the arachidonic acid (AA) metabolic network and be used as new anti-inflammatory drugs. In previous study, we discovered multi-target drugs towards the AA metabolic network, among which a dual-target inhibitor (JMC08-4) for human nonpancreatic secretory phospholipase A2 (hnps-PLA 2) and human leukotriene A4 hydrolase (LTA4H-h) was found. Based on the structure of compound JMC08-4, new dual-target inhibitors were designed assisted by molecular docking. In this report, a series of 5-hydroxytryptamine compounds were synthesized; and most of these title compounds showed more potent inhibitory activity than compound JMC08-4 in the in vitro bioassay against these two enzymes. The best one inhibited hnps-PLA 2 and LTA4H-h with IC50 values of 9.2 ± 0.5 μM and 2.4 ± 1.4 μM, respectively.
- Meng, Hu,Liu, Ying,Zhai, Yujing,Lai, Luhua
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p. 160 - 167
(2013/03/13)
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- Study on the structure-activity relations of brominated hydroxy diphenyl ethers derivatives with anilines
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In order to study the influence of anilines on antibacterial activity, eight novel brominated hydroxy diphenyl ethers derivatives were designed and synthesized. The antibacterial activities of the new compounds were tested via agar-well diffusion method in vitro under different concentrations. The results showed the derivatives had antibacterial activities at the concentration 50 μg/mL against Staphylococcus aureus SC and Staphylococcus aureus ATCC26112.
- Luo, Bin,Zhou, Hua-Hong,Yu, Kang-Kang,Wu, Kai-Qun,Chen, Tian,Wang, Yu-Liang
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p. 3863 - 3866
(2013/05/08)
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- Metal- and ligand-free Ullmann-type C-O and C-N coupling reactions promoted by potassium tert-butoxide
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A simple, metal- and ligand-free procedure for the Ullmann-type C-O coupling reactions has been achieved by allowing aryl bromides to react with a variety of phenols in the presence of t-BuOK. Moderate to excellent yields of O-arylation products are obtained under mild conditions in a short time. In addition, two examples of C-N coupling reactions are also reported. A benzyne mechanism is proposed according to the experiment data.
- Yang, Shuliang,Wu, Cunqi,Ruan, Mingbo,Yang, Yanqin,Zhao, Yongxia,Niu, Jiajia,Yang, Wei,Xu, Jingwei
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supporting information; experimental part
p. 4288 - 4292
(2012/09/22)
-
- INHIBITION OF P38 KINASE ACTIVITY USING SUBSTITUTED HETEROCYCLIC UREAS
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This invention relates to the use of a group of aryl ureas in treating cytokine mediated diseases, other than cancer and proteolytic enzyme mediated diseases, other than cancer, and pharmaceutical compositions for use in such therapy.
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Page/Page column 17
(2012/03/10)
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- Design, synthesis and antitumor activity of novel cis-furoquinoline derivatives
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A series of novel cis-furoquinoline derivatives was synthesized and tested for their antitumor activities in vitro against HepG2 cells, Lu-04 cells and Leu02 cells to evaluate structure-activity relationships. Assay-based antiproliferative activity study revealed that several compounds had significant effects on cytotoxicity, among which compounds 2f, 2l, 2q were found to be the most active compounds. Above all, compounds 2f, 2l, 2q would be potential anticancer agents which deserved further research.
- Li, Jie,Pei, Shuchen,Zhu, Yingxi,Wu, Jianbo,Chen, Yin,Zhang, Weiyu,Wu, Yong
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experimental part
p. 379 - 388
(2012/07/03)
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- Discovery of dual target inhibitors against cyclooxygenases and leukotriene A4 hydrolyase
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Dual target inhibitors against COX-2 and LTA4H were designed by adding functional groups from a marketed COX-2 inhibitor, Nimesulide, to an existing LTA4H inhibitor 1-(2-(4-phenoxyphenoxy) ethyl) pyrrolidine. A series of phenoxyphenyl pyrrolidine compounds were synthesized and tested for their inhibition activities using enzyme assays and human whole blood assay. Introduction of small electron withdrawing groups like NO2 and CF3 in the ortho-position of the terminal phenyl ring was found to change the original single target LTA4H inhibitor to dual target LTA4H and COX-2 inhibitors. Compound 5a and 5m showed dual LTA 4H and COX-2 inhibition activities in the enzyme assays and the HWB assay with IC50 values in the micromolar to submicromolar range. As their activities in HWB assay were comparable to the two starting single target inhibitors, the two compounds are promising for further studies. The strategy used in the current study may be generally applicable to other dual target drug designs.
- Chen, Zheng,Wu, Yiran,Liu, Ying,Yang, Suijia,Chen, Yunjie,Lai, Luhua
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experimental part
p. 3650 - 3660
(2011/07/08)
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- Open air O-arylation reaction of phenols with aryl halides catalyzed by polymer-anchored copper(II) complexes
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Two copper complexes were synthesized from macroporous chloromethylated polystyrene beads. The first one was prepared by sequential attachment of imidazole and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer, and the second one was prepared from 4-vinylpyridine and copper acetate with chloromethylated polystyrene-divinyl benzene copolymer. These catalysts showed excellent catalytic activity in O-arylation reaction of aryl halides with phenol in dimethylsulfoxide using potassium carbonate at 130 °C under open air conditions to give diaryl ethers in high yields. Less reactive aryl bromides and aryl chlorides have also been shown to react with phenols to give good yields of the diaryl ethers. The effects of various parameters such as solvent, catalyst from different copper salt and base on the reaction system were studied. The reaction is applicable to a wide variety of substituted aryl halides and phenols with different steric and electronic properties. These catalysts were recovered by simple filtration, and the reusability experiments showed that these catalysts can be used five times without much loss in the catalytic activity.
- Islam, Manirul,Mondal, Sanchita,Mondal, Paramita,Roy, Anupam Singha,Hossain, Dildar,Mobarak, Manir
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experimental part
p. 1 - 11
(2012/02/01)
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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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- 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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- Fe3O4@mesoporouspolyaniline: A highly efficient and magnetically separable catalyst for cross-coupling of aryl chlorides and phenols
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A high surface, magnetic Fe3O4@mesoporouspolyaniline core-shell nanocomposite was synthesized from magnetic iron oxide (Fe 3O4) nanoparticles and mesoporouspolyaniline (mPANI). The novel porous magnetic Fe3O4 was obtained by solvothermal method under sealed pressure reactor at high temperature to achieve high surface area. The mesoporouspolyaniline shell was synthesized by in situ surface polymerization onto porous magnetic Fe3O4 in the presence of polyvinylpyrrolidone (PVP) and sodium dodecylbenzenesulfonate (SDBS), as a linker and structure-directing agent, through 'blackberry nanostructures' assembly. The material composition, stoichiometric ratio and reaction conditions play vital roles in the synthesis of these nanostructures as confirmed by variety of characterization techniques. The role of the mesoporouspolyaniline shell is to stabilize the porous magnetic Fe3O4 nanoparticles, and provide direct access to the core Fe3O4 nanoparticles. The catalytic activity of magnetic Fe3O 4@mesoporousPANI nanocomposite was evaluated in the cross-coupling of aryl chlorides and phenols. Copyright
- Arundhathi,Damodara,Likhar, Pravin R.,Kantam, M. Lakshmi,Saravanan,Magdaleno, Travis,Kwon, Sun Hee
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supporting information; experimental part
p. 1591 - 1600
(2011/08/03)
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- Dimethyl sulfoxide/potassium hydroxide: A superbase for the transition metal-free preparation of cross-coupling products
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Potassium hydroxide (KOH) in dimethyl sulfoxide (DMSO) forms a superbasic medium that allows one to access cross-coupling products from reactions between aryl halides with various sulfur-, oxygen- and nitrogen-based nucleophiles under transition metal-free conditions. Copyright
- Yuan, Yu,Thome, Isabelle,Kim, Seok Hwan,Chen, Duanteng,Beyer, Astrid,Bonnamour, Julien,Zuidema, Erik,Chang, Sukbok,Bolm, Carsten
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experimental part
p. 2892 - 2898
(2011/01/05)
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- CuI nanoparticles for C-N and C-O cross coupling of heterocyclic amines and phenols with chlorobenzenes
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(Chemical Equation Presented) Employing CuI nanoparticles as an efficient catalyst for the cross-coupling reactions of various N/O nucleophilic reagents with aryl chlorides could be successfully carried out under mild conditions in the absence of both the ligands and strong bases. A variety of products including N-arylimidazoles and aryl ethers were synthesized in good to excellent yields. 2009 American Chemical Society.
- Sreedhar,Arundhathi,Reddy, P. Linga,Kantam, M. Lakshmi
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supporting information; experimental part
p. 7951 - 7954
(2010/01/16)
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- (2-Pyridyl)acetone-promoted Cu-catalyzed O-arylation of phenols with aryl iodides, bromides, and chlorides
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(Chemical Equation Presented) Employing (2-pyridyl)acetone as a new supporting ligand, the copper-catalyzed coupling reactions of aryl chlorides, aryl bromides, and aryl iodides with various phenols successfully proceeded in good yields under mild conditions. This reaction displays great functional groups compatibility and excellent reactive selectivity.
- Zhang, Qi,Wang, Deping,Wang, Xianyang,Ding, Ke
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supporting information; experimental part
p. 7187 - 7190
(2009/12/09)
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- Efficient catalytic activity of copper/aluminum hydrotalcite in diaryl ether synthesis
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A simple copper/aluminum hydrotalcite (Cu/Al-HT) catalyzed arylation of phenols with aryl iodides afforded the corresponding diaryl ethers in moderate to excellent yields. This ligand- free Cu/Al-HT catalyzed coupling of aryl iodides with phenols resulted in high yields of diaryl ethers in the absence of an additive. The catalyst was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles. Georg Thieme Verlag Stuttgart New York.
- Sreedhar,Arundhathi,Reddy, M. Amarnath,Kantam, M. Lakshmi
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experimental part
p. 483 - 487
(2009/07/11)
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- P(i-BuNCH2CH2)3N: an efficient promoter for the microwave synthesis of diaryl ethers
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With the title proazaphosphatrane as a promoter, the coupling of aryl fluorides with aryl TBDMS ethers under microwave conditions gave moderate to high yields of the desired products at low catalyst loadings and in short times. In this methodology, electron deficient aryl fluorides possessing substituents, such as nitro, cyano, and ester, were coupled with sterically demanding aryl TBDMS ethers as well as with aryl TBDMS ethers bearing a variety of functionalities such as methoxy, halo, and cyano groups.
- Raders, Steven M.,Verkade, John G.
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p. 3507 - 3511
(2008/09/21)
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- Inhibition Of Raf Kinase Using Symmetrical And Unsymmetrical Substituted Diphenyl Ureas
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This invention relates to the use of a group of aryl ureas in treating raf mediated diseases, and pharmaceutical compositions for use in such therapy.
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Page/Page column 14
(2008/12/04)
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- Discovery of novel and potent aryl diamines as leukotriene A4 hydrolase inhibitors
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The synthesis and biological evaluation of a series of aryl diamines as inhibitors of LTA4-h inhibitors are described. The optimization which led to the identification of the optimal para-substitution on the diphenyl ether moiety and diamine spacer is discussed. The resulting compounds such as 3l have excellent enzyme and cellular potency as well as desirable pharmacokinetic properties.
- Khim, Seock-Kyu,Bauman, John,Evans, Jarred,Freeman, Beverly,King, Beverly,Kirkland, Thomas,Kochanny, Monica,Lentz, Dao,Liang, Amy,Mendoza, Lisa,Phillips, Gary,Tseng, Jih-Lie,Wei, Robert G.,Ye, Hong,Yu, Limei,Parkinson, John,Guilford, William J.
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scheme or table
p. 3895 - 3898
(2009/04/07)
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- DBU-mediated mild and chemoselective deprotection of aryl silyl ethers and tandem biaryl ether formation
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An efficient method for the selective cleavage of aryl silyl ethers is established using 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU). With either 1.0 or 0.10 equivalent of DBU, smooth desilylation of various aryl silyl ethers was accomplished selectively in the presence of alkyl silyl ethers and other base-sensitive groups such as acetate and ester. In addition, direct transformation of aryl silyl ethers into biaryl ethers using a catalytic amount of DBU was possible through tandem desilylation and SNAr reaction with activated aryl fluorides. Georg Thieme Verlag Stuttgart.
- Yeom, Chang-Eun,Kim, Hye Won,Lee, So Young,Kim, B. Moon
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p. 146 - 150
(2008/03/13)
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- Synthesis of dictyomedins using phosphazene base catalyzed diaryl ether formation
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Dictyomedins isolated from dictyostelium cellular slime molds were synthesized by using diaryl ether derivatives as key intermediates for the cyclization to dibenzofuran followed by palladium catalyzed intramolecular biaryl formation.
- Ebisawa, Masaru,Ueno, Masahiro,Oshima, Yoshiteru,Kondo, Yoshinori
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p. 8918 - 8921
(2008/03/14)
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- INHIBITION OF RAF KINASE USING SUBSTITUTED HETEROCYCLIC UREAS
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Methods of treating tumors mediated by raf kinase, with substituted urea compounds, and such compounds per se.
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Page/Page column 17
(2010/11/28)
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- PYRIMIDINE DERIVATIVES FOR TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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Pyrimidine derivatives of formula (I), pharmaceutical compositions containing these compounds, and methods of using these compounds in treatment of hyperproliferative diseases such as cancer are disclosed and claimed.
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Page/Page column 44-45
(2010/11/23)
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- PYRIMIDINE DERIVATIVES FOR TREATMENT OF HYPERPROLIFERATIVE DISORDERS
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Pyrimidine derivatives of formula (I) in which J and Y represent aromatic or heteroaromatic rings; R2, G, G', and G" represent substituent groups and R2a represents H or halogen; L represents a linking group; and M represents CH or N. Pharmaceutical compositions containing these compounds, and methods of using these compounds in treatment of hyperproliferative diseases such as cancer are also disclosed and claimed.
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Page/Page column 59-60
(2008/06/13)
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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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- P(i-BuNCH2CH2)3N: An efficient promoter for the nucleophilic aromatic substitution reaction of aryl fluorides with aryl TBDMS (or TMS) ethers
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(Chemical Equation Presented) The nucleophilic aromatic substitution reaction between electron-deficient aryl fluorides and aryl TBDMS (or TMS) ethers has been shown to be efficiently promoted by proazaphosphatranes such as P(i-BuNCH2CH2)3N (3). Excellent yields of diaryl ether products were obtained under unusually mild conditions.
- Urgaonkar, Sameer,Verkade, John G.
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p. 3319 - 3322
(2007/10/03)
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