- Design and synthesis of a cyclitol-derived scaffold with axial pyridyl appendages and its encapsulation of the silver(I) cation
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Conversion of a myo-inositol derivative into a scyllo-inositol-derived scaffold with C3ν symmetry bearing three axial pyridyl appendages is presented. This pre-organized hexadentate ligand allows complexation of silver(I). The crystal structure of the complex was established.
- Leo, Pierre-Marc,Morin, Christophe,Philouze, Christian
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- Fabrication and covalent modification of highly chelated hybrid material based on silica-bipyridine framework for efficient adsorption of heavy metals: Isotherms, kinetics and thermodynamics studies
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Adsorbent materials are essential in clean-up processes. Research of efficient materials is a well-established technology. In this work, a novel and excellent host for heavy metals was synthesized by covalent immobilization of bipyridine tripodal receptor onto silica particles. The new engineered surface was well analyzed and evaluated by BET, BJH, EA, FT-IR, SEM, TGA and solid-state 13C NMR. The adsorption properties were investigated using Pb(ii), Cd(ii), Zn(ii) and Cu(ii) metals by varying all relevant parameters such as pH, contact time, concentration, thermodynamic parameters, kinetics, Langmuir and Freundlich isotherms, etc. The hybrid material has been found to exhibit high distribution coefficients for heavy metals. Adsorption kinetics follows a pseudo-second-order model, as a rapid process as evidenced by equilibrium achieved within 20 min. The resulting adsorption isotherms of the material were better represented by the Langmuir model than the Freundlich model. The thermodynamic parameters (ΔH°, ΔS° and ΔG°) revealed that the adsorption was endothermic and spontaneous. In addition, the proposed material demonstrates a high degree of reusability over a number of cycles, thus enhancing its potential for application in heavy metals recycling. All metal ions were determined by atomic absorption measurements.
- Radi, Smaail,Tighadouini, Said,Bacquet, Maryse,Degoutin, Stéphanie,Janus, Ludovic,Mabkhot, Yahia N.
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- 2-(N-Methylbenzyl)pyridine: A Potential Liquid Organic Hydrogen Carrier with Fast H2 Release and Stable Activity in Consecutive Cycles
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The liquid organic hydrogen carrier (LOHC) 2-(N-methylbenzyl)pyridine (MBP) shows good potential for H2 storage based on reversible hydrogenation and dehydrogenation, with an H2 storage density of 6.15 wt %. This material and the corresponding perhydro product (H12-MBP) are liquids at room temperature. Remarkably, H2 release is much faster from H12-MBP over Pd/C than from the benchmark perhydro benzyltoluene over Pt/C at lower temperatures than 270 °C, owing to the addition of N atom into the benzene ring. Since this positive effect is unfavorable to the hydrogenation reaction, more Ru/Al2O3 catalyst or prolonged reaction time must be applied for complete H2 storage. Experiments with repeated hydrogenation–dehydrogenation cycles reveal that reversible H2 storage and release are possible without degradation of the MBP/H12-MBP pair. The prepared MBP satisfies the requirements for chemical stability, handling properties, and cytotoxicity testing.
- Oh, Jinho,Jeong, Kwanyong,Kim, Tae Wan,Kwon, Hyunguk,Han, Jeong Woo,Park, Ji Hoon,Suh, Young-Woong
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- Structure-guided optimization of 1H-imidazole-2-carboxylic acid derivatives affording potent VIM-Type metallo-β-lactamase inhibitors
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Production of metallo-β-lactamases (MBLs) in bacterial pathogens is an important cause of resistance to the ‘last-resort’ carbapenem antibiotics. Development of effective MBL inhibitors to reverse carbapenem resistance in Gram-negative bacteria is still needed. We herein report X-ray structure-guided optimization of 1H-imidazole-2-carboxylic acid (ICA) derivatives by considering how to engage with the active-site flexible loops and improve penetration into Gram-negative bacteria. Structure-activity relationship studies revealed the importance of appropriate substituents at ICA 1-position to achieve potent inhibition to class B1 MBLs, particularly the Verona Integron-encoded MBLs (VIMs), mainly by involving ingenious interactions with the flexible active site loops as observed by crystallographic analyses. Of the tested ICA inhibitors, 55 displayed potent synergistic antibacterial activity with meropenem against engineered Escherichia coli strains and even intractable clinically isolated Pseudomonas aeruginosa producing VIM-2 MBL. The morphologic and internal structural changes of bacterial cells after treatment further demonstrated that 55 crossed the outer membrane and reversed the activity of meropenem. Moreover, 55 showed good pharmacokinetic and safety profile in vivo, which could be a potential candidate for combating VIM-mediated Gram-negative carbapenem resistance.
- Yan, Yu-Hang,Li, Wenfang,Chen, Wei,Li, Chao,Zhu, Kai-Rong,Deng, Ji,Dai, Qing-Qing,Yang, Ling-Ling,Wang, Zhenling,Li, Guo-Bo
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- Rapid and Effective Reaction of 2-Methylpyridin-N-oxides with Triphosgene via a [3,3]-Sigmatropic Rearrangement: Mechanism and Applications
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A facile and effective synthesis of 2-chloromethylpyridines was developed by a one-pot reaction of 2-alkylpyridin-N-oxides and triphosgene at room temperature. As starting materials, N-oxides of 2-alkylpyridine derivatives, including 2-alkylpyridines, 2-methyl quinolines, and phenanthroline, can react rapidly with triphosgene in the presence of triethylamine, affording 2-chloromethylpyridines in good to excellent yields (52-95%). Using the 2-methylquinoline substrate for the mechanistic study, it has been well demonstrated that the chlorination reaction undergoes a [3,3]-sigmatropic rearrangement, which can be observed as a reversible process by monitoring the intermediates. Moreover, the chlorination reaction can be used to construct a rapid and sensitive fluorescent probe for the detection of phosgene.
- Li, Hao,Nie, Fang-Yuan,Song, Qin-Hua,Xia, Hong-Cheng
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p. 8308 - 8318
(2021/06/28)
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- Synthesis of 1,2,3-triazole derivatives of hydnocarpic acid isolated from carpotroche brasiliensis seed oil and evaluation of antiproliferative activity
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Carpotroche brasiliensis is a tree native to Brazil, belonging to the family Flacurtiaceae, whose seeds contain a group of cyclopentenyl fatty acids: Gorlic (12%), chaulmugric (27%), and hydnocarpic (48.7%). These compounds are considered the main therapeutic agents in the treatment of leprosy. In the present study, a series of novel triazole compounds were obtained by conjugation between hydnocarpic acid and functionalized azides via copper(I)-catalyzed azidealkyne cycloaddition reaction (CuAAC). Hydnocarpic acid and its derivatives were tested against estrogen-positive breast carcinoma (MCF-7), hepatocellular carcinoma (HepG2), and non-small cell lung cancer (A549) cell lines. The (R)-(1-(pyridin-2-ylmethyl)-1H-1,2,3-triazol-4-yl)methyl-11-(cyclopent-2-en-1-yl)undecanoate (8) displayed promising antiproliferative activity against A549 cells. We demonstrated that this compound selectively inhibited the viability of A549 cell cultures. Furthermore, compound 8 inhibited the clonogenic capacity of A549 cells, and this effect was associated to its ability to inhibit cell cycle progression at G1 phase. These findings indicate that 8 is a promising antitumor agent on A549 cells and support further studies to evaluate the molecular mechanisms underlying its antiproliferative activity. In addition, hydnocarpic acid should be considered as a promising chemical prototype to obtain novel antineoplastic agents.
- De Sousa, Bianca L.,Demuner, Antonio J.,Dos Santos, Marcelo H.,Ferraz, Guilherme O.,Ferreira-Silva, Guilherme A.,Ionta, Marisa,Osorio, Liseth S.,Pilau, Eduardo J.,Silva, Evandro,Vareja?, Eduardo V. V.
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p. 2500 - 2510
(2020/11/18)
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- The Method of Producing Aromatic Compound Comprising Pyridin Group
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Hydrogen gen storage (Hydrogen Storage) The present invention relates to a method for producing an aromatic compound comprising a pyridine group usable as a Hydrogen Storage (Hydrogen Storage) material for supplying hydrogen to a device using hydrogen, such as a fuel cell and a hydrogen combustion device. More particularly, the present invention relates to a process for preparing an aromatic compound comprising a pyridine group using an oxidation reaction, a halogenation reaction, and Friedel-Craraft (Friririel-Craft) reaction of a pyridine derivative. (by machine translation)
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Paragraph 0088; 0096-0098
(2020/10/13)
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- Regioselective Synthesis of 1-Sulfanyl- and 1-Selanylindolizines
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We describe herein a new approach to prepare unprecedented bioactive indolizine motifs decorated with organosulfur and organoselenium groups. A total of 12 1-sulfanylindolizines and 2 1-selanylindolizines were prepared in excellent yields by an intramolecular annulation of easily prepared chalcogen-containing pyridinium salts. The reaction is fast (1 h at 70 °C or 5 min under sonication) and transition-metal-free, using glycerol as a green solvent.
- Penteado, Filipe,Gomes, Caroline S.,Perin, Gelson,Garcia, Cleisson S.,Bortolatto, Cristiani F.,Brüning, César A.,Lenard?o, Eder J.
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p. 7189 - 7198
(2019/06/14)
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- O-H and (CO)N-H bond weakening by coordination to Fe(ii)
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New N,N′-dimethyl-N,N′-bis(2-pyridylmethyl)-ethane-1,2-diamine derivatives bearing covalently linked OH and (CO)NH groups have been synthesized. The coordination of those pendant hydroxyl/amide groups to a Fe(ii) metal center is demonstrated both in solution, even in the presence of chloride as the counterion, and in solid state, by means of X-ray diffraction crystal structures. As a result of this coordination, the experimental bond dissociation free energies (BDFE) of O-H and (CO)N-H bonds are remarkably diminished down to 76.0 and 80.5 kcal mol-1 respectively, which is also in agreement with DFT-based theoretical calculations. These BDFE values are in the range of commonly used hydrogen-atom donor reagents. The strategy presented here allows an unequivocal evaluation of the influence of metal coordination in X-H bond weakening in organic solvents which could be easily extended to other metal centers.
- Resa, Sandra,Millán, Alba,Fuentes, Noelia,Crovetto, Luis,Luisa Marcos,Lezama, Luis,Choquesillo-Lazarte, Duane,Blanco, Victor,Campa?a, Araceli G.,Cárdenas, Diego J.,Cuerva, Juan M.
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supporting information
p. 2179 - 2189
(2019/02/12)
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- Designed To React: Terminal Copper Nitrenes and Their Application in Catalytic C?H Aminations
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Heteroscorpionate ligands of the bis(pyrazolyl)methane family have been applied in the stabilisation of terminal copper tosyl nitrenes. These species are highly active intermediates in the copper-catalysed direct C?H amination and nitrene transfer. Novel perfluoroalkyl-pyrazolyl- and pyridinyl-containing ligands were synthesized to coordinate to a reactive copper nitrene centre. Four distinct copper tosyl nitrenes were prepared at low temperatures by the reaction with SO2tBuPhINTs and copper(I) acetonitrile complexes. Their stoichiometric reactivity has been elucidated regarding the imination of phosphines and the aziridination of styrenes. The formation and thermal decay of the copper nitrenes were investigated by UV/Vis spectroscopy of the highly coloured species. Additionally, the compounds were studied by cryo-UHR-ESI mass spectrometry and DFT calculations. In addition, a mild catalytic procedure has been developed where the copper nitrene precursors enable the C?H amination of cyclohexane and toluene and the aziridination of styrenes.
- Moegling, Julian,Hoffmann, Alexander,Thomas, Fabian,Orth, Nicole,Liebh?user, Patricia,Herber, Ulrich,Rampmaier, Robert,Stanek, Julia,Fink, Gerhard,Ivanovi?-Burmazovi?, Ivana,Herres-Pawlis, Sonja
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supporting information
p. 9154 - 9159
(2018/07/25)
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- Surface-active ionic liquids for palladium-catalysed cross coupling in water: Effect of ionic liquid concentration on the catalytically active species
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We report the design and synthesis of surface-active ionic liquids for application in palladium-catalyzed cross coupling reactions. A series of dodecylimidazolium-based ionic liquids were applied as additives in the Heck reaction of ethyl acrylate and iodobenzene, and high yields of >90% could be obtained in water without the addition of further ligands. Our results indicate that the ionic liquid concentration in water is the key factor affecting the formation of the catalytically active species and hence the yield. Moreover, imidazolium-based ionic liquids that are able to form a carbene species differ significantly from conventional cationic surfactants, as a concentration dependent formation of the N-heterocyclic carbene complex was observed.
- Taskin, Meltem,Cognigni, Alice,Zirbs, Ronald,Reimhult, Erik,Bica, Katharina
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p. 41144 - 41151
(2017/09/02)
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- Design and synthesis of basic ionic liquids for the esterification of triterpenic acids
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Abstract: We present the design and synthesis of Br?nsted-basic ionic liquids and investigate their application in the microwave-assisted esterification of betulinic acid, aiming towards a benign and pyridine-free manufacturing process of the anti-HIV drug, bevirimat. Graphical abstract: [Figure not available: see fulltext.]
- Ressmann, Anna K.,Schneider, Maria,Gaertner, Peter,Weil, Matthias,Bica, Katharina
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p. 139 - 148
(2017/01/17)
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- Improved Halogenation of Methyl Aromatics and Methyl Heteroaromatics: Unexpected Reactivity of Tetrahalogeno-diphenylglycolurils
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1,3,4,6-Tetrachloro (TCDGU) and 1,3,4,6-tetrabromo-3α,6α-diphenylglycolurils smooth halogen oxidizers have been exploited in a new direction as reagents for free radical substitution toward some N-halosuccinimide nonreactive bis-heterocycles. An unexpected selectivity and reactivity were observed with methyl benzenes, methyl heterocycles, and methyl-bis-heterocycles of interest. A chemometric study has been performed to optimize five independent factors of the chlorination reaction with TCDGU. The predictive model was established either for the halogenation conversion and the ratio of monochlorination.
- Moretti, Florian,Poisson, Guillaume,Marsura, Alain
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p. 173 - 183
(2016/05/19)
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- Indenyl Compounds with Constrained Hapticity: The Effect of Strong Intramolecular Coordination
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A series of cyclopentadienyl and indenyl molybdenum(II) compounds with intramolecularly coordinated pyridine arms, including scorpionate-like species bearing two irreversibly coordinated arms on the indenyl core, were synthesized and characterized. All presented structural types were confirmed by X-ray diffraction analysis. Owing to the strong nucleophilicity of pyridine, the intramolecular interaction was found to be considerably stronger than that in analogous species bearing tertiary amines in the side chain. Although the starting compounds for the syntheses were isostructural, the reaction outcomes differed considerably. The cyclopentadienyl precursor gave a pentacoordinate η5:κN-compound, whereas the indenyl analogue produced a hexacoordinate species with the unprecedented η3:κN-coordination mode of the indenyl ligand and thus represents an unusual example of the so-called indenyl effect. The unusually high stability of the η3:κN-coordination compounds toward η3to η5haptotropic rearrangement was clarified by theoretical calculations. As the strong intramolecular interaction prevented rotation of the indenyl moiety, it could not reach the conformation suitable for the η3to η5rearrangement. As a result, the low hapticity was effectively locked.
- Mrózek, Ond?ej,Vinklárek, Jaromír,R??i?ková, Zdeňka,Honzí?ek, Jan
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p. 5250 - 5264
(2016/11/23)
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- Pyridine-phosphinimine ligand-accelerated Cu(I)-catalyzed azide-alkyne cycloaddition for preparation of 1-(pyridin-2-yl)-1,2,3-triazole derivatives
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A series of phosphinimine ligands were designed and used in the Cu(i)-catalyzed azide-alkyne cycloaddition (CuAAC) reaction of tetrazolo[1,5-a]pyridines and alkynes for the first time. By optimizing the reaction conditions, an efficient catalytic system (CuCl/2-PyCH 2NPtBu3) was developed to give 1-(pyridin-2-yl)-1,2,3-triazole derivatives in moderate to excellent yields (46-98%). This journal is the Partner Organisations 2014.
- Sun, Ranfeng,Wang, Huangdong,Hu, Jianfeng,Zhao, Jiudong,Zhang, Hao
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p. 5954 - 5963
(2014/08/05)
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- Divalent transition metal(II) complexes of two heterocyclic ligands with pendant pyridinyl groups: Synthesis, characterization and electrochemistry
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Treatment of the pentadentate macrocyclic ligand 4-(pyridin-2-ylmethyl)-1, 7-dithia-4,10-diazacyclododecane, L, and the hexadentate macrocyclic ligand 4,10-bis(pyridin-2-ylmethyl)-1,7-dithia-4,10-diazacyclododecane, L′, with one equivalent of a M2+ metal salt (M = Co, Ni, Cu) in methanol yielded six mononuclear complexes, [CoL(MeCN)](ClO4)2 (1), [NiL(H2O)]Cl2 (2), [CuL(MeCN)](ClO4) 2 (3) and [ML′](ClO4)2 (4-6). Their solid state crystal structures were determined using X-ray single crystal diffraction analysis. In complexes 1-3, the metal centres exhibit a slightly distorted octahedral geometry, resulting from the coordination of three nitrogen and two sulfur donating atoms in the ligand L and one solvent molecule (MeCN for complexes 1 and 3, water for complex 2) whereas in complexes 4-6, the coordination around the metal centres was satisfied by four nitrogen and two sulfur atoms from the ligand L′. The electronic spectra and electrochemistry of these complexes are reported
- Wei, Zhenhong,Peng, Yan,Hughes, David L.,Zhao, Jia,Huang, Lingman,Liu, Xiaoming
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p. 181 - 187
(2014/01/17)
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- Staging bonding between group 12 metal ions and neutral selenium donors: Intermolecular interactions of mixed N,Se donor ligands and anions
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The versatile pyridyl synthons of mixed N,Se donor ligands bis(pyridin-2-ylmethyl)selane (L) and 1,2-bis(pyridin-2-ylmethyl)diselane (L&) served the dual roles of metal chelating anchors and mediators of supramolecular associations in a crystallographic approach to documenting uncommon bonding between divalent Group 12 metal ions and neutral selenium functionalities. Five new molecular species with diverse ligand configurations and conformations were structurally characterized. Two macrocyclic polymorphs of [ZnLCl2] have intermolecular Se-Cl interactions rather than the desired intramolecular Zn-Se binding. Rare examples of Cd(II)-selenoether bonding are provided by tricoordinate L in dinuclear [CdLCl(μ-Cl)]2 and mononuclear [CdL(μ-NO3)2]. Unique intramolecular Zn-selenoether and Cd-diselenide bonds are reported for [ZnL(μ-NO3)2] and [CdL(μ-NO3)2], respectively. In addition, a cocrystal of [CdL(μ-NO3)2] and [CdL&(μ-NO3)2] is structurally characterized. The intermolecular pyridyl &-interactions observed in these diverse structures are highlighted.
- Hain, Malia S.,Fukuda, Yoko,Rojas Ramrez, Carolina,Winer, Benjamin Y.,Winslow, Stephanie E.,Pike, Robert D.,Bebout, Deborah C.
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p. 6497 - 6507
(2015/02/19)
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- Molecular tectonics: Pyridyl containing thiacalix[4]arene based tectons for the generation of 2- and 3-D silver coordination networks
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Three new organic tectons (2-4) based on the p-tert-butylthiacalix[4]arene backbone, blocked in the 1,3-alternate conformation, bearing four pyridyl coordinating moieties, have been synthesised and characterised in the solid state. The ligands are positional isomers and differ by the position of the N atom on the pyridyl unit (ortho for 2, meta for 3 and para for 4). Their combination with the Ag+ cation leads, reproducibly, to the formation of 2- and 3-D infinite silver coordination networks. Independent of the nature of the anion, the combination of 2 offering four (N,S) type chelates with the Ag+ cation affords an unprecedented diamond type 3D network. Both 3 and 4, behaving as tetrakis monodentate ligands, lead to the formation of 2-D architectures. The Royal Society of Chemistry 2013.
- Ovsyannikov,Lang,Ferlay,Solovieva,Antipin,Konovalov,Kyritsakas,Hosseini
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p. 116 - 126
(2013/02/22)
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- Copper(II) complexes of tetradentate pyridyl ligands supported on keggin polyoxometalates: Single-crystal to single-crystal transformations promoted by reversible dehydration processes
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Two new hybrid compounds constructed from Keggin type polyoxometalates and copper(II) complexes of tetradentate ligands containing amine and pyridyl groups, namely [Cu(bpmen)(H2O)][SiW12O 40{Cu(bpmen)}] (1) and [SiW12O40{Cu(bpmpn) (H2O)}2]·3H2O (2) (bpmen, N,N′-dimethyl-N,N′-bis-(pyridin-2-ylmethyl)-1,2-diaminoethane; bpmpn, N,N′-dimethyl-N,N′-bis(pyridin-2-ylmethyl)-1,3- diaminopropane), have been synthesized under hydrothermal conditions and characterized by elemental analyses and infrared and Raman spectroscopy. Thermal stability of 1 and 2 has been studied by means of thermogravimetric analyses and variable temperature powder X-ray diffraction. Both compounds undergo single-crystal to single-crystal transformations promoted by reversible dehydration processes that have been followed by single-crystal X-ray diffraction. Structures of 1 and 2, and also of their corresponding anhydrous phases 1a and 2a, have been established. The layered structure of 1 shows rows of monodecorated polyanions with complex cations occupying intralamellar spaces, whereas trans-didecorated species in 2 lead to stacked honeycomb-like metal-organic layers forming channels where Keggin clusters are accommodated. Structural differences relate to changes in the complex geometry and ligand conformation when going from bpmen to bpmpn. Dehydration of 1 promotes coordination of the complex countercation and consequent formation of a cis-didecorated species in 1a, whereas changes in the structure of 2a are more subtle. Structural variations upon dehydration are reflected in the electron paramagnetic resonance spectra.
- Iturrospe, Amaia,Artetxe, Benat,Reinoso, Santiago,San Felices, Leire,Vitoria, Pablo,Lezama, Luis,Gutierrez-Zorrilla, Juan M.
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p. 3084 - 3093
(2013/04/24)
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- Synthesis and spectral studies of 2-[(N-ethyl carbazole)-3-sulfonyl ethylenediamine]-1-N,N-2-(2-methypyridy) as a fluorescence probe for Zn 2+
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A novel Zn2+ fluorescence probe, 2-[(N-ethyl carbazole)-3-sulfonyl ethylenediamine]-1-N,N-bis(2-methypyrbidy), was designed and synthesized via simple steps, and its structure was confirmed by IR and 1H NMR. The probe gives significant fluorescence enhancement immediately following Zn2+ addition at neutral pH and exhibits improved selectivity for Zn2+ compared to the other metal ions in aqueous solution. The spectra and fluorescence quantum yield of the synthesized compound were carefully investigated by UV-vis absorption and fluorescence spectra in various solvents.
- Zhang, Jun,Cui, Huiling,Hojo, Masashi,Shuang, Shaomin,Dong, Chuan
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supporting information; experimental part
p. 343 - 346
(2012/03/11)
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- Efficient synthesis of a new series of piperidine ring-modified analogs of (±)-threo-methyl phenyl(piperidin-2-yl)acetate
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A series of novel piperidine ring modified analogs of (±)-threo- methyl phenyl (piperidin-2-yl)acetate was synthesized by direct alkylation and reductive amination procedure, using sodium borohydride over molecular sieves. The chemical structures of these compounds were established based on mass spectra, 1H NMR spectra, and CHN elemental analysis data. Several significant modifications in the literature methodologies were made to make the reaction more efficient, and good yields were generally obtained. Copyright Taylor & Francis Group, LLC.
- Ojo, Babatunde
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experimental part
p. 1731 - 1745
(2012/06/29)
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- From chelate C,N-cyclopalladated oximes to C,N,N′-, C,N,S -, or C,N,C′-pincer palladium(II) complexes by formation of oxime ether ligands
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Pincer complexes of the types [Pd{C,N,N′-Ar{C(Me)=NOCH 2py-2}-2}X] or [Pd{C,N,S-C6H4{C(Me)=NOCH 2SMe}-2}Cl] (Ar = C6H4, C6H(OMe) 3-4,5,6; py-2 = 2-pyridyl; X = Cl, Br) have been prepared by reacting cyclopalladated oxime complexes [Pd{C,N-Ar{C(Me)=NOH}-2}(μ-Cl)]2 with XCH2py-2 or ClCH2SMe, respectively, in the presence of KtBuO. Various neutral and cationic derivatives have been synthesized as well as iminobenzoyl complexes resulting from the insertion of isocyanide into their Pd-Caryl bond. The cycloaddition of MeO 2CC≡CCO2Me to the oximato complex [Pd{C,N-C 6H4{C(Me)=NO}-2}(tBubpy)] (tBubpy = 4,4′-di-tert-butyl-2,2′-bipyridine) in the presence of various neutral L ligands produces pincer complexes [Pd{C,N,C′-C6H 4{C(Me)=NOC(CO2Me)=C(CO2Me)}-2}L]. Complexes of each one of the new types have been characterized by X-ray diffraction methods.
- Abellan-Lopez, Antonio,Chicote, Maria-Teresa,Bautista, Delia,Vicente, Jose
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p. 7434 - 7446
(2013/01/15)
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- Treatment of alcohols with tosyl chloride does not always lead to the formation of tosylates
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Treatment of substituted benzyl alcohols with tosyl chloride resulted in the formation of the corresponding chlorides, not the usual tosylates. A series of experiments demonstrated that it was possible to predict whether chlorination or tosylation would occur for substituted benzyl alcohols and pyridine methanols. Treatment of electron withdrawing group-substituted benzyl alcohols with tosyl chloride gave the corresponding chlorides in moderate yields under mild conditions, which provided a simple way to directly prepare chlorides from alcohols.
- Ding, Rui,He, Yong,Wang, Xiao,Xu, Jingli,Chen, Yurong,Feng, Man,Qi, Chuanmin
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experimental part
p. 5665 - 5673
(2011/09/20)
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- Studies on novel 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones as potential TACE inhibitors: Design, synthesis, molecular modeling, and preliminary biological evaluation
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Compounds belonging to the class of 2-imidazolidinones and tetrahydropyrimidin-2(1H)-ones were synthesized and evaluated for their TACE inhibitory activity. Most of the compounds showed very good TACE inhibitory activity. Docking study clearly indicates importance of the P1′ group of the inhibitor for the TACE inhibitory activity. This work proves that these two classes of molecules could be used as potential leads for the development of TACE inhibitors.
- DasGupta, Shirshendu,Murumkar, Prashant R.,Giridhar, Rajani,Yadav, Mange Ram
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experimental part
p. 3604 - 3617
(2009/09/30)
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- TRIAZOLO [4, 5-D] PYRAMIDINE DERIVATIVES AND THEIR USE AS PURINE RECEPTOR ANTAGONISTS
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Compounds of formula (I) that are capable of acting as purine receptor antagonists, pharmaceutical compositions including the compounds, and methods of making the compounds, are. disclosed. The compounds and compositions can be used in treating or preventing disorders related to purine receptor hyperfunctioning.
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(2010/01/30)
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- PYRIDINE DERIVATIVES SUBSTITUTED BY HETEROCYCLIC RING AND PHOSPHONOAMINO GROUP, AND ANTI-FUNGAL AGENT CONTAINING SAME
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Anti-fungal agent having excellent anti-fungal action physicochemical properties including safety and water solubility. Compound represented by formula (I), or salt thereof: wherein R1 represents hydrogen, halogen, amino, R11-NH- wherein R11 represents C1-6 alkyl, hydroxy C1-6 alkyl, C1-6 alkoxy C1-6 alkyl, or C1-6alkoxycarbonyl C1-6 alkyl, R12-(CO)-NH- wherein R12 represents C1-6 alkyl group or C1-6 alkoxy C1-6 alkyl, C1-6 alkyl, hydroxy C1-6 alkyl, cyano C1-6 alkyl, C1-6 alkoxy, or C1-6 alkoxy C1-6 alkyl or a phosphonoamino group; R2 represents hydrogen, C1-6 alkyl, amino, or a di C1-6 alkylamino group or a phosphonoamino group; one of X and Y is nitrogen while the other is nitrogen or oxygen; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, oxygen, sulfur, -CH2O-, -OCH2-, -NH-, -CH2NH-, -NHCH2-, -CH2S-, or -SCH2-; R3 represents hydrogen or halogen or C1-6 alkyl, C3-8 cycloalkyl, C6-10 aryl, a 5- or 6-member heteroaryl group or a 5- or 6-member nonaromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents hydrogen or halogen; provided that either R1 or R2 represents a phosphonoamino group.
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(2009/04/24)
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- PYRIDINE DERIVATIVE SUBSTITUTED BY HETEROARYL RING, AND ANTIFUNGAL AGENT COMPRISING THE SAME
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The present invention provides an antifungal agent that has excellent antifungal action, and is also excellent in terms of its properties, safety, and metabolic stability. The present invention discloses a compound represented by the following formula I or a salt thereof, and an antifungal agent comprising the compound or the salt: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group, or a C1-6-alkoxy-C1-6-alkyl group; R2 represents a hydrogen atom or an amino group; X, Y, Z, and W independently represent a nitrogen atom, an oxygen atom, a sulfur atom, or -CH-, provided that at least two among X, Y, and W are nitrogen atoms; the ring A represents a 5- or 6-membered heteroaryl ring or a benzene ring; Q represents a methylene group, an oxygen atom, -CH2O-, -OCH2-, -NH-, -NHCH2-, or -CH2NH-; and R3 represents a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, or a 5- or 6-membered heteroaryl group, each of which may have one or two substituents.
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(2009/06/27)
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- Nickel and iron complexes with N,P,N-type ligands: Synthesis, structure and catalytic oligomerization of ethylene
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The N,P,N-type ligands bis(2-picolyl)phenylphosphine (1), bis(4,5-dihydro-2-oxazolylmethyl)phenylphosphine (2), bis(4,4-dimethyl-2- oxazolylmethyl)phenylphosphine (3) and bis(2-picolyloxy)phenylphosphine (4) were used to synthesize the corresponding pentacoordinated Ni(ii) complexes [Ni{bis(2-picolyl)phenylphosphine}Cl2] (6), [Ni{bis(4,5-dihydro-2- oxazolylmethyl)phenylphosphine}Cl2] (7), [Ni{bis(4,4-dimethyl-2- oxazolylmethyl)phenylphosphine}Cl2] (8) and [Ni{bis(2-picolyloxy) phenylphosphine}Cl2] (9), respectively. The hexacoordinated iron complexes [Fe{bis(2-picolyl)phenylphosphine}2][Cl 3FeOFeCl3] (10), [Fe{bis(4,5-dihydro-2-oxazolylmethyl) phenylphosphine}2][Cl3FeOFeCl3] (11) and the tetracoordinated complex [Fe{bis(4,4-dimethyl-2-oxazolylmethyl)phenylphosphine} Cl2] (abbreviated [FeCl2(NPNMe2-N,N)]) were prepared by reaction of FeCl2?4H2O with ligands 1-3, respectively. The crystal structures of the octahedral complexes 10 and 11, determined by X-ray diffraction, showed that two tridentate ligands are facially coordinated to the metal centre with a cis-arrangement of the P atoms and the dianion (μ-oxo)bis[trichloroferrate(iii)] compensates the doubly positive charge of the complex. The cyclic voltammograms of 10 and 11 showed two reversible redox couples attributed to the reduction of the dianion (Fe 2OCl6)2- (-0.24 V for 10 and -0.20 V for 11vs. SCE) and to the oxidation of the Fe(ii) ion of the complex (0.67 V for 10 and 0.52 V for 11vs. SCE). The cyclic voltammogram of [FeCl2(NPN Me2-N,N)] showed a reversible redox couple at -0.17 V vs. SCE assigned to the oxidation of the Fe(ii) atom and an irreversible process at 0.65 V. The complexes 6, 8-11 and [FeCl2(NPNMe2-N,N)] have been evaluated in the catalytic oligomerization of ethylene with AlEtCl 2 or MAO as cocatalyst. The nickel complex 6 proved to be the most active precatalyst in the series, with a turnover frequency (TOF) of 61 800 molC2H4 molNi-1 h -1 with 10 equiv. of AlEtCl2 and 12 200 mol C2H4 molNi-1 h-1 with 200 equiv. of MAO. Precatalysts 8 and 9 were the most selective in butenes, up to 90% with 6 equiv. of AlEtCl2 and 89% with 2 equiv. of AlEtCl 2, respectively, and up to 92% butenes with 400 equiv. of MAO and 91% butenes with 200 equiv. MAO, respectively. The best selectivities for 1-butene were provided by 8 and AlEtCl2 (up to 31% with 6 equiv.) and 9 with MAO (up to 72% with 200 equiv.). The iron complexes were not significantly active with AlEtCl2 or MAO as cocatalyst. The Royal Society of Chemistry 2008.
- Kermagoret, Anthony,Tomicki, Falk,Braunstein, Pierre
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p. 2945 - 2955
(2008/09/21)
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- Heterocycles substituted pyridine derivatives and antifungal agent containing thereof
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An object of the present invention is to provide an antifungal agent which has excellent antifungal effects and is superior in terms of its physical properties, safety and metabolic stability. According to the present invention, there is disclosed a compound represented by the following formula (I), or a salt thereof: wherein R1 represents a hydrogen atom, a halogen atom, an amino group, a C1-6 alkyl group, a C1-6 alkoxy group or a C1-6 alkoxy C1-6 alkyl group; R2 represents a hydrogen atom, a C1-6 alkyl group, an amino group or a di C1-6 alkylamino group; one of X and Y is a nitrogen atom while the other is a nitrogen atom or an oxygen atom; ring A represents a 5- or 6-member heteroaryl ring or a benzene ring which may have a halogen atom, or 1 or 2 C1-6 alkyl groups; Z represents a single bond, a methylene group, an ethylene group, an oxygen atom, a sulfur atom, —CH2O—, —OCH2—, —NH—, —CH2NH—, —NHCH2—, —CH2S—, or —SCH2—; R3 represents a hydrogen atom, a halogen atom, a C1-6 alkyl group, a C3-8 cycloalkyl group, a C6-10 aryl group, a 5- or 6-member heteroaryl group, or 5- or 6-member non-aromatic heterocyclic group which may have 1 or 2 substituents; and R4 represents a hydrogen atom or a halogen atom.
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Page/Page column 69
(2010/11/27)
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- SYNTHESIS OF DERIVATIVES OF GINKGOLIDE C
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The subject invention provides ginkgolide C derivatives compounds having the structure: wherein R is H or -A-Ar, where A is an alkyl group; and Ar is an aryl group, which may contain heteroatoms and may be unsubstituted or substituted by one to five substituents each selected from the group consisting of hydrogen, alkoxy, -CH2CO2R, and - CH2CONRR; where R is an alkyl group; and R and R are each, independently, hydrogen or a branched or unbranched alkyl group; wherein R is H or -COR, where R is alkyl, aryl or amino; wherein R is present or absent, and when present is H, COR or -CO-Z-R; where R is alkyl, aryl or amino; andZ is oxygen; wherein R is present or absent, and when present is -COR; where R is alkyl or aryl; wherein only one of R or R is present in the compound; wherein only two of R, R, R and R are H; and wherein each of a and b designates a single covalent bond which is present or absent, where bond a is present when R is absent and bond b is present when R is absent; or an optically pure enantiomer of the compound. Additionally, the subject invention provides methods of inhibiting the activity of a glycine receptor using these compounds.
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Page/Page column 57
(2010/02/11)
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- METHOD FOR PHOTOCHEMICAL HALOGENATION
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The inventive method consists in adding an acid which removes hydrogen halide, especially HCI contained in a reaction mixture and makes it possible to carry out photochemical halogenation, especially chlorination of organic components by substituting hydrogen-chlorine, although initial components, target components or eventually present amines form, together with free hydrogen halide, for example HCI additive products which could form precipitate without acidification
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- Utilities of olefin derivatives
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Compounds having an activity to enhance the expression of apoAI are provided. Compounds of formula (I): in which Ar1 and Ar2 are independently a phenyl, naphthyl, or monocyclic or bicyclic aromatic heterocyclic group, which may be optionally substituted; —X— is —N═CZ2-, —CY2═CZ2-, —CY2Y3—CHZ2-, —S—, —O—, or the like; Y1, Y2, Y3, Z1 and Z2 are independently a hydrogen, a halogen, a lower alkyl, a phenyl, or the like; Z1 and Z2 may be independently a linker group that may combine with Ar2 and Ar1 to form a condensed ring; m is 0 or 1, and n is 0 to 2; a prodrug thereof, a pharmaceutically acceptable salt or solvate of them; are disclosed.
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Page/Page column 12-13
(2008/06/13)
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- Inhibitors of aspartyl protease
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The present invention relates to a novel class of sulfonamides which are aspartyl protease inhibitors. In one embodiment, this invention relates to a novel class of HIV aspartyl protease inhibitors characterized by specific structural and physicochemical features. This invention also relates to pharmaceutical compositions comprising these compounds. The compounds and pharmaceutical compositions of this invention are particularly well suited for inhibiting HIV-1 and HIV-2 protease activity and consequently, may be advantageously used as anti-viral agents against the HIV-1 and HIV-2 viruses. This invention also relates to methods for inhibiting the activity of HIV aspartyl protease using the compounds of this invention and methods for screening compounds for anti-HIV activity.
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- Facile and Selective Synthesis of Chloromethylpyridines and Chloropyridines Using Diphosgene/Triphosgene
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Diphosgene and triphosgene in the presence of amines were found to be an excellent chlorinating agents with high selectivity for the preparation of chloromethylpyridines and chloropyridines from picoline-N-oxides and pyridine-N-oxides respectively.
- Narendar,Gangadasu,Ramesh, Ch.,Raju, B. China,Rao, V. Jayathirtha
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p. 1097 - 1103
(2007/10/03)
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- Tyrosine kinase inhibitors
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The present invention relates to compounds which inhibit, regulate and/or modulate tyrosine kinase signal transduction, compositions which contain these compounds, and methods of using them to treat tyrosine kinase-dependent diseases and conditions, such as angiogenesis, cancer, tumor growth, atherosclerosis, age related macular degeneration, diabetic retinopathy, inflammatory diseases, and the like in mammals.
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- Pyrazolopyrimidinone CGMP PDE5 inhibitors for the treatment of sexual dysfunction
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There is provided compounds of formula IA and of formula IB, wherein R1, R2, R3, R4and A have meanings given in the description, which are useful in the curative and prophylactic treatment of a medical condition for which inhibition of a cyclic guanosine 3′,5′-monophosphate phosphodiesterase (e.g. cGMP PDE5) is desired.
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Page column 25
(2010/02/05)
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- Substituted biphenyls
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Substituted biphenyls having glucagon receptor antagonistic activity. Claimed compounds have the formula wherein R1aand R1bindependently represent (C1-C6) alkyl; R2represents (C1-C10) alkyl or substituted (C1-C10) alkyl wherein the substituents are independently from 1 to 3 of —SR7; R7represents phenyl, or substituted phenyl wherein the substituents are independently 1-5 of halogen, trifluoromethyl, (C1-C6) alkyl, (C1-C6) alkoxy, nitro, cyano, or hydroxyl; R3represents substituted (C1-C6) alkyl wherein the substituents are 1-2 hydroxyl groups; G represents a substituent selected from the group consisting of halogen, (C1-C6) alkyl, and OR4wherein R4is H or (C1-C6) alkyl; and y is 0 or an integer of 1-3. Pharmaceutical compositions containing such compounds and methods of treatment of glucagon-mediated conditions by administering such compounds are also claimed.
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- Triazole derivatives
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The present invention relates to triazole and imidazole derivatives of formula I and to their pharmaceutically acceptable acid addition salts. These compounds are NMDA receptor subtype blockers and are useful for the treatment of diseases related to the NMDA receptor.
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- Efficient pyridinylmethyl functionalization: Synthesis of 10,10-bis[(2-fluoro-4-pyridinyl)methyl]-9(10H)-anthracenone (DMP 543), an acetylcholine release enhancing agent
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2-Fluoro-4-methylpyridine (3) is efficiently functionalized by chlorination, hydrolysis and methane-sulfonylation into the novel alkylating agent 7. This mesylate is used for the bisalkylation of anthrone under carefully defined conditions to prepare the cognition enhancer drug candidate 1. This process proceeds in up to 37% overall yield and is adaptable for large scale synthesis.
- Pesti,Huhn,Yin,Xing,Fortunak,Earl
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p. 7718 - 7722
(2007/10/03)
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- A series of non-quinoline cysLT1 receptor antagonists: SAR study on pyridyl analogs of Singulair
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The structure-activity relationship of a series of styrylpyridine analogs of MK-0476 (montelukast, Singular) is described. This work has led to the identification of a number of potent and orally active cysLT1 receptor (LTD4 receptor) antagonists including 2ab (L-733,321) as an optimized candidate.
- Guay, Daniel,Gauthier,Dufresne,Jones,McAuliffe,McFarlane,Metters,Prasit,Rochette,Roy,Sawyer,Zamboni
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p. 453 - 458
(2007/10/03)
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- Syntheses and structures of N,N′-bis(6-(2-hydroxymethyl)pyridylmethyl)piperazine, its two zinc(II) complexes and the cadmium(II) complex of N-(6-(2-hydroxymethyl)pyridylmethyl)-N′-(2-pyridylmethyl)piperazine
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The syntheses and crystal structures of N,N′-bis(6-(2-hydroxymethyl)-pyridylmethyl)piperazine (C18H24N4O2, 3), its polymeric zinc(II) nitrate complex (C18H29N7O14Zn2, 3a) and dinuclear zinc(II) chloride complex (C20H27N5O2Zn2Cl 4, 3b) and mononuclear cadmium(II) nitrate complex of N-(6-(2-hydroxymethyl)pyridylmethyl)-N′-(2-pyridylmethyl)piperazine (C17H22N6O7Cd, 4a) are described. Compound 3 was characterised by 1H and 13C NMR, mass spectrometry and elementary analysis. The structures of all compounds were determined by single crystal X-ray diffraction methods. Crystal data: 3: monoclinic, space group P21/n (no. 14), a=7.816(1), b=6.699(1), c= 16.567(3) A, β=91.94(1)°, V=866.9(2) A3, Z=2; 3a: monoclinic, space group P2/n (no. 13), a=10.274(1), b=11.018(1), C=11.615(1) A, β=93.13(1)°, V= 1312.8(2) A3, Z=2; 3b: triclinic, space group P1 (no. 2), a=9.624(1), b= 11.381(1), c=14.016(1) A, α=106.21(1), β=102.73(1), γ=107.10(1)°, V= 1323.9(2) A3, Z=2; 4a: monoclinic, space group P21/c (no. 14), a=13.589(8), b=9.006(5), c=17.472(8) A, β=101.96(4)°, V=2092(2) A3, Z=4. In the metal complexes, zinc has a distorted square-pyramidal coordination and cadmium has a pentagonal bipyramidal coordination. In 3a and 3b, three coordination sites are occupied by one oxygen and two nitrogens of hexadentate 3 and the remaining two by the bridging hydroxyl group and a terminal water molecule in 3a and by two terminal chlorine atoms in 3b. In 4a, five coordination sites of cadmium are occupied by four nitrogens and one oxygen of the pentadentate ligand, and the remaining two by monodentate nitrate groups. Acta Chemica Scandinavica 1998.
- Loukiala, Satumari,Ratilainen, Jari,Airola, Karri,Valkonen, Jussi,Rissanen, Kari
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p. 593 - 602
(2007/10/03)
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- Structure-activity relationship of 2-[[(2-Pyridyl)methyl]thio]-1H- benzimidazoles as anti Helicobacter pylori agents in vitro and evaluation of their in vivo efficacy
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A relationship between the structure of 21 2-[[(2-pyridyl)methyl]thio]- 1H-benzimidazoles (6) and their anti Helicobacter pylori activity expressed as minimum bactericidal concentration (MBC) values is described. Observed MBCs ranged from 256 to 1 μg/mL. The structure - activity relationship (SAR) showed that larger and more lipophilic compounds, especially compounds with such substituents in the 4-position of the pyridyl moiety, generally had lower MBC values. Four new compounds 'that were predicted to be potent by the established SAR model were synthesized and tested. One such compound, i.e., 2-[[(4-[(cyclopropylmethyl)oxy]3-methyl-2-pyridyl)methyl]thio]-1H- benzimidazole (18), was tested for in vivo efficacy in a mouse Helicobacter felis model (125 μmol/kg bid given orally for 4 days, n = 4). Unfortunately, antibacterial activity could not be clearly demonstrated in this model. Instead a potent acid secretion inhibition was observed. This finding was attributed to the methylthio compound being oxidized to the corresponding methyl sulfinyl derivative, i.e., a proton pump inhibitor, in vivo. Although the antibacterial activity had the potential of decreasing H. felis cell counts in vivo the proton pump inhibitory effect became dominant and actually promoted H. felis cell growth. Hence, we conclude that the antibacterial utility of the 2-[[(2-pyridyl)methyl]thio]1H-benzimidazoles (6) as a compound class is compromised by their propensity to become proton pump inhibitors upon metabolic oxidation in vivo.
- Kühler, Thomas C.,Swanson, Marianne,Shcherbuchin, Vladimir,Larsson, H?kan,Mellg?rd, Bj?rn,Sj?str?m, Jan-Eric
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p. 1777 - 1788
(2007/10/03)
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- Development of orally active oxytocin antagonists: Studies on 1-(1-{4- [1-(2-methyl-1-oxidopyridin-3-ylmethyl)piperidin-4-yloxy].2methoxybenzoyl}- 4-yl)-1,4-dihydrobenz[d][1,3]oxazin-2-one (L-372,662) and related pyridines
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The previously reported oxytocin antagonist L-371,257 (2) has been modified at its acetylpiperidine terminus to incorporate various pyridine N- oxide groups. This modification has led to the identification of compounds with improved pharmacokinetics and excellent oral bioavailability. The pyridine N-oxide series is exemplified by L-372,662 (30), which possessed good potency in vitro (Ki = 4.1 nM, cloned human oxytocin receptor) and in vivo (intravenous AD50 = 0.71 mg/kg in the rat), excellent oral bioavailability (90% in the rat, 96% in the dog), good aqueous solubility (>8.5 mg/mL at pH 5.2) which should facilitate formulation for iv administration, and excellent selectivity against the human arginine vasopressin receptors. Incorporation of a 5-fluoro substituent on the central benzoyl ring of this class of oxytocin antagonists enhanced in vitro and in vivo potency but was detrimental to the pharmacokinetic profiles of these compounds. Although lipophilic substitution around the pyridine ring of compound 30 gave higher affinity in vitro, such substituents were a metabolic liability and caused shortfalls in vivo. Two approaches to prevent this metabolism, addition of a cyclic constraint and incorporation of trifluoromethyl groups, were examined. The former approach was ineffective because of metabolic hydroxylation on the constrained ring system, whereas the latter showed improvement in plasma pharmacokinetics in some cases.
- Bell, Ian M.,Erb, Jill M.,Freidinger, Roger M.,Gallicchio, Steven N.,Guare, James P.,Guidotti, Maribeth T.,Halpin, Rita A.,Hobbs, Doug W.,Homnick, Carl F.,Kuo, Michelle S.,Lis, Edward V.,Mathre, David J.,Michelson, Stuart R.,Pawluczy, Joseph M.,Pettibone, Douglas J.,Reiss, Duane R.,Vickers, Stanley,Williams, Peter D.,Woyden, Carla J.
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p. 2146 - 2163
(2007/10/03)
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- Esterification of carboxylic acid salts
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Mono- or polycarboxylic acid esters are prepared by reacting a salt of such carboxylic acid with an organic halocompound, e.g., a (cyclo)alkyl, (cyclo)alkenyl, aryl or aralkyl halide, in an aqueous reaction medium, in the presence of a catalytically effective amount of a phase transfer catalyst, for example an onium salt.
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- Condensed heterocyclic compounds, their production and use
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Compounds represented by the formula: STR1 wherein ring A is benzene; Ar is aromatic group; R1, R2 and R3 each stands for H, acyl, hydrocarbon or heterocyclic, or R2 and R3, taken together, may form non-aromatic cyclic hydrocarbon; X is methylene or carbonyl; ......... is single bond or double bond; when ......... is single bond, Y is --NR4 -- (R4 is H, acyl, hydrocarbon or heterocyclic), when ......... is double bond, Y is N; n is 1-3, provided that, X is carbonyl and, at the same time, R2 and R3, taken together, form non-aromatic cyclic hydrocarbon, ......... is double bond or R4 is a heterocyclic or --Z(CH2)m --W (Z is methylene or carbonyl, W is optionally substituted amino, and m denotes 0-5), or salts thereof have an excellent GnRH receptor antagonistic action and/or an action of improving sleep disturbances.
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- Regioselective complexation of new multiple piperazine/pyridine ligands: differentiation by113Cd-NMR spectroscopy
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Eleven novel piperazine containing open-chain ligands L1-L11 were designed to offer symmetrical and asymmetrical complexation sites for metal ions and were synthesized by repetitive synthetic method. The divergent use of aromatic bishalomethyl and mono-Af-alkylated piperazine compounds as spacers led to a series of long (up to M. W. = 836) oligomeric multidentate N-ligands. Due to the lack of solid state methods for structure analysis, an NMR technique using 113Cd nucleus as a probe in solution state was utilised. 113Cd chemical shifts were observed to be dependend on the coordination site and similar coordination sites in different ligands gave characteristically similar 113Cd chemical shifts. As a result 113Cd-NMR spectroscopy proved to be an excellent tool to distinguish between the structures of the different complexation sites on a nearly quantitative level. VCH Verlagsgesellschaft mbH,.
- Ratilaincn, Jari,Airola, Karri,Kolehmaincn, Erkki,Rissanen, Kari
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p. 1353 - 1359
(2007/10/03)
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- A new strategy for the synthesis of phosphorothioates of 2′-deoxyriboligonucleotides
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2-Picoline thiol, a new reagent, has been indigenously prepared and a new strategy has been followed for the sulphurization of phosphate bond in nucleotide monomer. The 2-picolylthiophosphorobis-(triazolide) has been prepared using phosphite triester approach and treated with protected nucleosides to get phosphorothioate synthons. The two dimers, d(GpT) and d(TpT) have been synthesised in very good yields using these synthons. The removal of 2-methylpyridyl group at the end of synthesis is achieved with 1,1,3,3-tetramethylguanidinium-4-nitrobenzaldoxime in dioxane-water.
- Kumar, Prabhat,Misra
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p. 1000 - 1004
(2007/10/03)
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- Optionally substituted pyrido[2,3-d]pyridine-2,4(1H,3H)-diones and pyrido[2,]pyrimidine-2(1H,3H)-ones
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The present invention relates to optionally substituted pyrido[2,3-d]pyrimidine-2,4(1H,3H)-diones or optionally substituted pyrido[2,3-d]pyrimidine-2(1H,3H)-ones, i.e., compounds of Formula I: STR1 wherein: Y is --CH2 -- or --C(O)--; R1 is hydrogen or --(CH2)n --R7, wherein: R7 is aryl or heteroaryl, and n is 1 or 2, provided that when Y is --C(O)--, R7 is heteroaryl; and R2, R3, R4, R5 and R6 are hydrogen, or one is selected from lower alkyl, halo, carboxy, methoxycarbonyl, carbamoyl, methylcarbamoyl, di-methylcarbamoyl, methylcarbonyl, methylthio, methylsulfinyl, methylsulfonyl, hydroxymethyl, amino, trifluoromethyl, cyano or nitro; or R2, R3, R4 and R5 are independently selected from hydrogen, lower alkyl, nitro, chloro, fluoro, methoxycarbonyl or methylcarbonyl, provided at least one is hydrogen, and R6 is hydrogen; or a pharmaceutically acceptable ester, ether or salt thereof.
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- 2--1H-thienoimidazoles. A Novel Class of Gastric H+/K+-ATPase Inhibitors
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2-thienoimidazoles were synthesized and investigated as potential inhibitors of gastric H+/K+-ATPase.The isomers of the two possible thienoimidazole series were found to be potent inhibitors of gastric acid secretion in vitro and in vivo.Structure-activity relationships indicate that especially lipophilic alkoxy, benzyloxy, and phenoxy substituents with additional electron-demanding properties in the 4-position of the pyridine moiety combined with an unsubstituted thienoimidazole lead to highly active compounds with a favorable chemical stability.Various substitution patterns in the thienoimidazole moiety result in lower biological activity.The heptafluorobutyloxy derivative saviprazole (HOE 731, 5d) was selected for further development and is currently undergoing clinical evaluation.Comprehensive pharmacological studies indicate a pharmacodynamic profile different to omeprazole, the first H+/K+-ATPase blocker introduced on the market.
- Weidmann, Klaus,Herling, Andreas W.,Lang, Hans-Jochen,Scheunemann, Karl-Heinz,Rippel, Robert,et al.
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p. 438 - 450
(2007/10/02)
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- Quinolinoxy phenylsulphonamides
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New phenylsulphonamide of the formula in which STR1 R1 represents a pyridyl, quinolyl or isoquinolyl radical which is unsubstituted or substituted by halogen, alkyl, cycloalkyl, alkoxy, cyano, nitro, halogenoalkyl, halogenoalkoxy, alkoxycarbonyl or alkylsulphonyl, R2 represents hydrogen, cyano, nitro, halogen, alkyl, alkoxy, halogenoalkyl, halogenoalkoxy or alkoxycarbonyl, R3 represents an aryl radical which is unsubstituted or monosubstituted, disubstituted or trisubstituted by halogen, halogenoalkyl, halogenoalkoxy, alkyl, alkoxy, alkylthio, alkylsulphonyl, cyano, nitro or alkoxycarbonyl, the substituents being identical or different, or represents pentafluorophenyl or represents a straight-chain, branched or cyclic alkyl which is unsubstituted or substituted by halogen, aryl, aryloxy, cyano, alkoxycarbonyl, alkoxy, alkylthio or trifluoromethyl, and X represents an --O--, --A--B-- or --B--A-- group where A denotes --O--, STR2 and B denotes --CH2 -- or STR3 where R1 does not represent a pyridyl radical when x represents an --O-- group, and salts thereof are prepared by reacting appropriate amines with sulphonyl halides. The substituted phenylsulphonamides can be employed as active compounds for inhibiting enzymatic reactions and for inhibiting thrombocyte aggregations.
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