- A HKUST-1 MOF inclusion compound with in-situ reduced copper(I) as [Cu(NCCH3)4]+cation complex in the octahedral A-type pore
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Hydrothermal reaction of racemic 1,2-bis(1,2,4-triazol-4-yl)propane (rac-btrip) and benzene-1,3,5-tricarboxylic acid (H3btc) with copper(II) acetate in an aqueous triethylamine and acetonitrile mixture afforded blue-green cuboctahedral crystals
- Tahli, Anas,Elshaarawy, Reda F.M.,K?c, ümit,Kautz, Anna Christin,Janiak, Christoph
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Read Online
- Differentiation of Epoxide Enantiomers in the Confined Spaces of an Homochiral Cu(II) Metal-Organic Framework by Kinetic Resolution
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TAMOF-1, a homochiral metal-organic framework (MOF) constructed from an amino acid derivative and Cu(II), was investigated as a heterogeneous catalyst in kinetic resolutions involving the ring opening of styrene oxide with a set of anilines. The branched
- Cabezas-Giménez, Juanjo,Lillo, Vanesa,Luis Nú?ez-Rico, José,Nieves Corella-Ochoa,Jover, Jesús,Galán-Mascarós, José Ramón,Vidal-Ferran, Anton
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supporting information
p. 16956 - 16965
(2021/07/16)
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- C6–O-alkylated 7-deazainosine nucleoside analogues: Discovery of potent and selective anti-sleeping sickness agents
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African trypanosomiasis, a deadly infectious disease caused by the protozoan Trypanosoma brucei spp., is spread to new hosts by bites of infected tsetse flies. Currently approved therapies all have their specific drawbacks, prompting a search for novel th
- Hulpia, Fabian,Bouton, Jakob,Campagnaro, Gustavo D.,Alfayez, Ibrahim A.,Mabille, Dorien,Maes, Louis,de Koning, Harry P.,Caljon, Guy,Van Calenbergh, Serge
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- Homochiral Metal-Organic Frameworks for Enantioselective Separations in Liquid Chromatography
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Selective separation of enantiomers is a substantial challenge for the pharmaceutical industry. Chromatography on chiral stationary phases is the standard method, but at a very high cost for industrial-scale purification due to the high cost of the chiral stationary phases. Typically, these materials are poorly robust, expensive to manufacture, and often too specific for a single desired substrate, lacking desirable versatility across different chiral analytes. Here, we disclose a porous, robust homochiral metal-organic framework (MOF), TAMOF-1, built from copper(II) and an affordable linker prepared from natural l-histidine. TAMOF-1 has shown to be able to separate a variety of model racemic mixtures, including drugs, in a wide range of solvents of different polarity, outperforming several commercial chiral columns for HPLC separations. Although not exploited in the present article, it is worthy to mention that the preparation of this new material is scalable to the multikilogram scale, opening unprecedented possibilities for low-energy chiral separation at the industrial scale.
- Corella-Ochoa, M. Nieves,Tapia, Jesús B.,Rubin, Heather N.,Lillo, Vanesa,González-Cobos, Jesús,Nú?ez-Rico, José Luis,Balestra, Salvador R.G.,Almora-Barrios, Neyvis,Lledós, Marina,Gu?ll-Bara, Arnau,Cabezas-Giménez, Juanjo,Escudero-Adán, Eduardo C.,Vidal-Ferran, Anton,Calero, Sofiá,Reynolds, Melissa,Martí-Gastaldo, Carlos,Galán-Mascarós, José Ramón
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p. 14306 - 14316
(2019/10/11)
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- Practical Synthesis of a 6-Triazolylazabicyclo[3.1.0]hexane
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We describe a practical, scalable synthesis of an advanced heterocyclic intermediate, (1R,5S,6s)-6-(4H-1,2,4-triazol-4-yl)-3-azabicyclo[3.1.0]hexane. A robust synthetic sequence based on a Kulinkovich-de Meijere pyrroline cyclopropanation followed by tran
- Sirois, Lauren E.,Xu, Jie,Angelaud, Remy,Lao, David,Gosselin, Francis
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p. 728 - 735
(2018/06/26)
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- A CRYSTALLINE METAL ORGANIC FRAMEWORK
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The present invention relates to a crystalline metal organic framework which comprises repeating units of formula (RR)-(IA)or (SS)-(IA)or (RS)-(IA) or (SR)-(IA); or alternatively of formula (RR)-(IB) or (SS)-(IB) or (RS)-(IB) or (SR)-(IB) and acomposition containing it. It also relates to processes for their preparation and theiruses as a separation agent and as a catalyst.
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Page/Page column 35
(2018/05/16)
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- Homochiral zinc benzene-1,3,5-tricarboxylate coordination networks with a chiral nitrogen ligand or template: Spontaneous resolution of a twofold interpenetrated 2D SQL (4,4) network and formation of enantiopure 3D sra (SrAl2) networks
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A pair of homochiral enantiomorphic two-fold interpenetrated, mixed-ligand coordination polymers (CPs), 2D-{[Zn(μ-Hbtc)(μ-R-btrip)]·H2O}n 1 and 2D-{[Zn(μ-Hbtc)(μ-S-btrip)]·H2O}n 2, were found in a racemic conglo
- Tahli, Anas,Chamayou, Anne-Christine,K?c, ümit,Brückner, Robin,Elshaarawy, Reda F.M.,Heering, Christian,Janiak, Christoph
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p. 190 - 201
(2016/06/14)
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- Selective and reusable iron(II)-based molecular sensor for the vapor-phase detection of alcohols
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A mononuclear iron(II) neutral complex (1) is screened for sensing abilities for a wide spectrum of chemicals and to evaluate the response function toward physical perturbation like temperature and mechanical stress. Interestingly, 1 precisely detects methanol among an alcohol series. The sensing process is visually detectable, fatigue-resistant, highly selective, and reusable. The sensing ability is attributed to molecular sieving and subsequent spin-state change of iron centers, after a crystal-to-crystal transformation.
- Naik, Anil D.,Robeyns, Koen,Meunier, Christophe F.,Leonard, Alexandre F.,Rotaru, Aurelian,Tinant, Bernard,Filinchuk, Yaroslav,Su, Bao Lian,Garcia, Yann
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supporting information
p. 1263 - 1265
(2014/03/21)
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- ANTIBACTERIAL PIPERIDINYL SUBSTITUTED 3,4-DIHYDRO-1H-[1,8]NAPHTHYRIDINONES
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The present invention is related to novel compounds of formula (I) that inhibit the activity of the Fab1 enzyme which are therefore useful in the treatment of bacterial infections. It further relates to pharmaceutical compositions comprising these compounds, and chemical processes for preparing these compounds.
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Page/Page column 27
(2013/03/26)
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- Reaction of aminobenzoate esters with N,N′-dimethylformamide azine dihydrochloride: Crucial influence of intramolecular hydrogen bonding for the formation of 1,2,4-triazoles
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The reaction of N,N′-dimethylformamide azine (DMFA) or its dihydrochloride derivative (DMFA·2HCl) with o-RO(O)CC6H 4NH2 (R = Me, Et) leads to co-crystallization products o-RO(O)CC6H4NH2·DMFA (R = Me, Et), while the same reaction of DMFA·2HCl with m- and p-RO(O)CC6H 4NH2 (R = Me, Et) provides the corresponding 4-substituted 1,2,4-triazoles (1-4). Reaction of the same m- and p-substituted amines with DMFA has failed, while addition of a few drops of HCl or HNO3 in this reaction mixture has allowed us to obtain the corresponding triazole derivatives. Thus, the direct transamination reaction with the formation of triazoles 1-4 is catalysed by acidic catalysts. Molecular structures of DMFA, o-EtO(O)CC6H4NH2·DMFA and 3 were elucidated by X-ray diffraction. The Royal Society of Chemistry 2012.
- Railliet, Antoine P.,Safin, Damir A.,Robeyns, Koen,Garcia, Yann
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experimental part
p. 4812 - 4818
(2012/08/14)
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- Isoindolinone inhibitors of the murine double minute 2 (MFM2)-p53 protein-protein interaction: Structure-activity studies leading to improved potency
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Inhibition of the MDM2-p53 interaction has been shown to produce an antitumor effect, especially in MDM2 amplified tumors. The isoindolinone scaffold has proved to be versatile for the discovery of MDM2-p53 antagonists. Optimization of previously reported inhibitors, for example, NU8231 (7) and NU8165 (49), was guided by MDM2 NMR titrations, which indicated key areas of the binding interaction to be explored. Variation of the 2-N-benzyl and 3-alkoxy substituents resulted in the identification of 3-(4-chlorophenyl)-3-((1- (hydroxymethyl)cyclopropyl)methoxy)-2-(4-nitrobenzyl)isoindolin-1-one (74) as a potent MDM2-p53 inhibitor (IC50 = 0.23 A± 0.01 μM). Resolution of the enantiomers of 74 showed that potent MDM2-p53 activity primarily resided with the (+)-R-enantiomer (74a; IC50 = 0.17 A± 0.02 μM). The cellular activity of key compounds has been examined in cell lines with defined p53 and MDM2 status. Compound 74a activates p53, MDM2, and p21 transcription in MDM2 amplified cells and shows moderate selectivity for wild-type p53 cell lines in growth inhibition assays.
- Hardcastle, Ian R.,Liu, Junfeng,Valeur, Eric,Watson, Anna,Ahmed, Shafiq U.,Blackburn, Timothy J.,Bennaceur, Karim,Clegg, William,Drummond, Catherine,Endicott, Jane A.,Golding, Bernard T.,Griffin, Roger J.,Gruber, Jan,Haggerty, Karen,Harrington, Ross W.,Hutton, Claire,Kemp, Stuart,Lu, Xiaohong,McDonnell, James M.,Newell, David R.,Noble, Martin E. M.,Payne, Sara L.,Revill, Charlotte H.,Riedinger, Christiane,Xu, Qing,Lunec, John
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supporting information; experimental part
p. 1233 - 1243
(2011/05/07)
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- Zinc complexes with 1,2,4-triazole functionalized amino acid derivatives: Synthesis, structure and β-lactamase assay
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Coordinating abilities of 4R-1,2,4-triazole derivatives (R = glycine ethyl ester (L1), glycine (L2), diethylamino malonate (L3), methionine (L4) and diethyl aminomethylphosphonate (L5)) towards ZnII ions have been studied in solution, in solid state and versus three zinc-β-lactamases. The crystal structure of [Zn3(L4)6(H2O) 6] (6) is described; it is the first crystal structure involving a 1,2,4-triazole functionalized methionine. It forms a trinuclear complex with central zinc octahedrally coordinated by only L4, whereas terminal zinc ions coordination sphere is completed by three water molecules. L4 exhibits a dual functionality of a bridging bidentate ligand as well as an anion. A dense hydrogen bonding network connects these trinuclear entity into a 3D supramolecular network. The ZnII ions in 6 are held at equidistance (3.848 A?) which coincidently matches with the corresponding Zn?Zn distance in the binuclear zinc enzyme from Bacillus cereus (3.848 and 4.365 A?). Among L1-L5 screened for β-lactamase assay, L4 shows modest inhibition for BcII enzyme.
- Naik, Anil D.,Beck, Joséphine,D?rtu, Marinela M.,Bebrone, Carine,Tinant, Bernard,Robeyns, Koen,Marchand-Brynaert, Jacqueline,Garcia, Yann
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scheme or table
p. 21 - 28
(2011/05/04)
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- Synthesis and crystal structure determination of 0D-, 1D- and 3D-metal compounds of 4-(pyrid-4-yl)-1,2,4-triazole with zinc(II) and cadmium(II)
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The potentially tritopic bridging ligand 4-(pyrid-4-yl)-1,2,4-triazole (pytz) reacts with cadmium(II) nitrate tetrahydrate, Cd(NO3) 2·4H2O and sodium dicyanamide (Na-dca) to form the molecular complex [Cd(dca)2(κNpy-pytz) 2(H2O)2] (1). The cadmium atom lies on a center of inversion and is coordinated in a slightly distorted octahedral geometry by the trans-oriented pytz ligands, dicyanamide anions and aqua ligands. The pytz ligand coordinates through the Npyridin atom to the metal atom. The molecular complexes are connected to a 3D supramolecular network by O-H?Ndca and O-H?Ntriazole hydrogen bonds. From zinc(II) bromide and pytz the compound 1D-[ZnBr2(μ- κNpy,Ntz-pytz)] (2) is obtained where the pytz-ligand bridges between the tetracoordinated zinc(II) atoms through coordination of its Npyridine- and Ntriazole-atoms. Adjacent chains are connected through C-H?Br and C-H?N hydrogen bonds to form a 3D supramolecular structure. Single crystals of 2 crystallize homochiral in the non-centrosymmetric space group P212 121. The origin of the homochirality is the formation of hydrogen-bonded helices around the 21 screw axes with the same sense of rotation (left-handed or M in the investigated crystal). Cd(NO 3)2·4H2O, pytz and sodium thiocyanate (NaSCN) give the framework 3D-[Cd(μ-SCN)2(μ-κN py,Ntz-pytz)] (3). Parallel layers of 2D-{Cd(μ-SCN) 2}-nets with distorted (6,3)-net topology are assembled by the bridging pytz-ligands into a 3D-structure. The pytz-ligand bridges between two cadmium atoms by Npyridine- and Ntriazole-coordination.
- Tahli, Anas,MacLaren, Jana K.,Boldog, Ishtvan,Janiak, Christoph
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body text
p. 506 - 513
(2011/09/20)
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- BENZIMIDAZOLE AND AZA-BENZIMIDAZOLE CARBOXAMIDES
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This invention provides compounds of Formula I which are PAFR antagonists: I and the pharmaceutically acceptable salts thereof. The compounds are useful for treating PAF-mediated disorders, and can be used in methods for treating atherosclerosis and preve
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Page/Page column 46
(2010/05/14)
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- BIARYL CARBOXAMIDES
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This invention provides compounds of Formula (I) which are PAFR antagonists: Formula (I) and the pharmaceutically acceptable salts thereof. The compounds are useful for treating PAF-mediated disorders, and can be used in methods for treating atherosclerosis and preventing or reducing risk for atherosclerotic disease events. The compounds are also useful for treating or ameliorating pain, e.g. inflammatory pain and/or nociceptive pain, and for treating or ameliorating autoimmune and/or inflammatory diseases, among other conditions.
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Page/Page column 44
(2010/08/04)
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- A new synthesis of N,N′-Bis(dimethylaminomethylene)hydrazine
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N,N′-Bis(dimethylaminomethylene)hydrazine was synthesized in a one-step procedure from N,N′-diformylhydrazine and tert-butoxy- bis(dimethylamino)methane (Bredereck-Simchen reagent) or N,N-dimethylformamide dimethylacetal. Georg Thieme Verlag Stuttgart.
- Kantlehner, Willi,Mezger, Jochen,Stoyanov, Edmont V.,Leonhardt, Sylvia
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experimental part
p. 3380 - 3382
(2009/05/07)
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- STRUCTURE OF THE PRODUCTS FROM CONDENSATION OF AMIDRAZONES WITH MONOCARBONYL COMPOUNDS
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The structure of the products from the reaction of amidrazones with monocarbonyl compounds was invwstigated by spectral methods (IR, UV, (1)H and (13)C NMR). 1-Monosubstituted acetamidrazones and benzamidrazones form 1,3,5,5-tetrasubstituted 4,5-dihydro-1,2,4-triazoles, and the unsubstituted amidrazones form alkylidyne derivatives.
- Zelenin, K.N.,Khrustalev, V.A.,Sergutina, V.P.
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p. 822 - 829
(2007/10/02)
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- 1,1,4,4,-TETRAALKYLAMIDAZINES. SYNTHESIS OF MONOALKYLHYDRAZINES
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A series of 1,1,4,4,-tetraalkylamidazines were synthesized.Their IR, UV, and 1H and 13C NMR spectra were investigated, and the characteristics of their stereochemical structure are discussed.Amidazines are alkylated by the action of alkyl iodides at the imine nitrogen atom.Alkaline cleavage of the alkyl iodide derivatives is a method for the production of monoalkylhydrazines.
- Zelenin, K. N.,Khrustalev, V. A.,Sergutina, V. P.
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p. 244 - 247
(2007/10/02)
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