- Fluorescent probe for fluorine ion detection, application of fluorescent probe and method for detecting fluorine ions in to-be-detected sample
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The invention belongs to the technical field of analytical chemistry, and particularly relates to a fluorescent probe for fluorine ion detection, application of the fluorescent probe and a method for detecting fluorine ions in a to-be-detected sample. The invention provides a compound as shown in a formula I, or an optical isomer or salt thereof, and provides application of the compound as a fluorine ion detection fluorescent probe. According to the method for detecting the fluorine ions in the to-be-detected sample, the compound, or the optical isomer or the salt of the compound is used as a fluorine ion detection fluorescent probe for detection. The fluorescent probe has the advantages of good water solubility, high selectivity, high response speed, low detection limit, good stability, wide applicable pH range and good application prospect.
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Paragraph 0047; 0052; 0060-0061
(2021/08/06)
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- An Electroreductive Approach to Radical Silylation via the Activation of Strong Si-Cl Bond
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The construction of C(sp3)-Si bonds is important in synthetic, medicinal, and materials chemistry. In this context, reactions mediated by silyl radicals have become increasingly attractive but methods for accessing these intermediates remain limited. We present a new strategy for silyl radical generation via electroreduction of readily available chlorosilanes. At highly biased potentials, electrochemistry grants access to silyl radicals through energetically uphill reductive cleavage of strong Si-Cl bonds. This strategy proved to be general in various alkene silylation reactions including disilylation, hydrosilylation, and allylic silylation under simple and transition-metal-free conditions.
- Lu, Lingxiang,Siu, Juno C.,Lai, Yihuan,Lin, Song
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supporting information
p. 21272 - 21278
(2020/12/21)
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- Cu/Chiral Phosphoric Acid-Catalyzed Asymmetric Three-Component Radical-Initiated 1,2-Dicarbofunctionalization of Alkenes
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An asymmetric intermolecular, three-component radical-initiated dicarbofunctionalization of 1,1-diarylalkenes with diverse carbon-centered radical precursors and electron-rich heteroaromatics by a copper(I) and chiral phosphoric acid cooperative catalysis strategy has been developed, providing straightforward access to chiral triarylmethanes bearing quaternary all-carbon stereocenters with high efficiency as well as excellent chemo- and enantioselectivity. The key to success is not only the introduction of a sterically demanding chiral phosphoric acid to favor radical difunctionalization over the otherwise remarkable side reactions but also the in situ generation of carbocation intermediates from benzylic radical to realize asymmetric induction with the aid of a removable hydroxy directing group via cooperative interactions with chiral phosphate. Density functional theory calculations elucidated the critical chiral environment created by the hydrogen-bonding and ion-pair interactions between the chiral phosphoric acid catalyst and substrates, which leads to the enantioselective C-C bond formation.
- Lin, Jin-Shun,Li, Tao-Tao,Liu, Ji-Ren,Jiao, Guan-Yuan,Gu, Qiang-Shuai,Cheng, Jiang-Tao,Guo, Yu-Long,Hong, Xin,Liu, Xin-Yuan
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supporting information
p. 1074 - 1083
(2019/01/11)
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- A fluoride activated methylene blue releasing platform for imaging and antimicrobial photodynamic therapy of human dental plaque
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We report a F- activated methylene blue (MB) releasing platform for imaging and antimicrobial photodynamic therapy (aPDT). By utilizing this platform, one of the selected probes, FD-F3, displays a remarkable near-infrared fluorescence and absor
- Wei, Peng,Xue, Fengfeng,Shi, Yunming,Strand, Ross,Chen, Hui,Yi, Tao
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supporting information
p. 13115 - 13118
(2018/11/30)
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- Carbonyl–Olefin Cross-Metathesis Through a Visible-Light-Induced 1,3-Diol Formation and Fragmentation Sequence
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A visible-light-mediated approach to carbonyl–olefin cross-metathesis is described. Photoinduced hole catalysis was used to promote the formation of 1,3-diols from aldehydes and styrenes, which were then readily fragmented under acidic conditions to form the cross-metathesis products. The use of 1,3-diols as intermediates, rather than the energetically more demanding oxetanes, provides a new, orthogonal mechanistic strategy for carbonyl–olefin cross-metathesis. Furthermore, this approach does not require any metals, ligands, or additives, and provides the products with high levels of E selectivity. A mechanistic rationale is provided and supported by both theoretical calculations and experiments. Additionally, a practical synthesis of a new acridinium-based photocatalyst, including full characterization, is presented.
- Pitzer, Lena,Sandfort, Frederik,Strieth-Kalthoff, Felix,Glorius, Frank
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supporting information
p. 16219 - 16223
(2018/11/23)
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- Synthesis method of isoliquiritigenin
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The invention relates to the technical field of organic synthesis, and particularly discloses a synthesis method of isoliquiritigenin. According to the synthesis method of isoliquiritigenin, 2,4-hydroxyacetophenone and 4-hydroxybenzaldehyde are used as raw materials, and the product namely isoliquiritigenin can be obtained through hydroxyl protection, aldol condensation and hydroxyl deprotection reaction. The synthesis method of isoliquiritigenin, provided by the invention, is simple and easy to implement, mild in reaction conditions, safe, reliable, high in raw material availability, low in price and low in cost, adopts at least one of dimethyl tert-butyl chlorosilane and triisopropyl chlorosilane to protect 4-hydroxyl groups of 4-hydroxybenzaldehyde and 2,4-dihydroxyacetophenone, reducesthe risk of byproduct generation, improves the yield of isoliquiritigenin, and is suitable for industrial production.
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Paragraph 0048-0050
(2018/09/13)
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- Heterotelechelic Polymers by Ring-Opening Metathesis and Regioselective Chain Transfer
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Heterotelechelic polymers were synthesized by a kinetic telechelic ring-opening metathesis polymerization method relying on the regioselective cross-metathesis of the propagating Grubbs’ first-generation catalyst with cinnamyl alcohol derivatives. This procedure allowed the synthesis of hetero-bis-end-functional polymers in a one-pot setup. The molecular weight of the polymers could be controlled by varying the ratio between cinnamyl alcohol derivatives and monomer. The end functional groups can be changed using different aromatically substituted cinnamyl alcohol derivatives. Different monomers were investigated and the presence of the functional groups was shown by NMR spectroscopy and MALDI-ToF mass spectrometry. Labeling experiments with dyes were conducted to demonstrate the orthogonal addressability of both chain ends of the heterotelechelic polymers obtained.
- Liu, Peng,Yasir, Mohammad,Ruggi, Albert,Kilbinger, Andreas F. M.
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supporting information
p. 914 - 917
(2018/01/01)
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- FLUORIDE FLUORESCENCE PROBE
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Methylene blue (MB) derivatives selectively detect F? by desilylation reaction to act as a fluorescent probe.
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Paragraph 0089-0091; 0092-0093
(2019/01/09)
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- A Modular Access to (±)-Tubocurine and (±)-Curine - Formal Total Synthesis of Tubocurarine
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Two consecutive Cu-catalyzed Ullmann-type C-O couplings permitted the first successful entry toward the curare alkaloids (±)-tubocurine and (±)-curine. Starting from vanillin, the synthetic sequence comprises 15 linear steps and includes a total of 24 transformations. In addition, the total synthesis of tubocurine represents a formal total synthesis of the famous arrow poison alkaloid tubocurarine.
- Otto, Nicola,Ferenc, Dorota,Opatz, Till
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p. 1205 - 1217
(2018/06/18)
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- METABOLICALLY ROBUST ANALOGS OF CYP-EICOSANOIDS FOR THE TREATMENT OF CARDIAC DISEASE
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The present invention relates to compounds according to general formula (I) which are metabolically robust analogues of bioactive lipid mediators derived from omega-3 polyunsaturated fatty acids (n-3 PUFAs).The present invention further relates to composi
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Page/Page column 81
(2017/02/09)
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- ANALOGS OF CYP-EICOSANOIDS FOR USE IN TREATING OR PREVENTING A DISORDER ASSOCIATED WITH NEOVASCULARIZATION AND/OR INFLAMMATION
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The present invention relates to compounds according to general formula (I) which are metabolically robust analogues of bioactive lipid mediators derived from omega-3 polyunsaturated fatty acids (n-3 PUFAs) for use in treating or reducing the risk of deve
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Page/Page column 82; 83
(2017/10/31)
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- Trisubstituted Imidazoles with a Rigidized Hinge Binding Motif Act As Single Digit nM Inhibitors of Clinically Relevant EGFR L858R/T790M and L858R/T790M/C797S Mutants: An Example of Target Hopping
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The high genomic instability of non-small cell lung cancer tumors leads to the rapid development of resistance against promising EGFR tyrosine kinase inhibitors (TKIs). A recently detected triple mutation compromises the activity of the gold standard third-generation EGFR inhibitors. We have prepared a set of trisubstituted imidazoles with a rigidized 7-azaindole hinge binding motif as a new structural class of EGFR inhibitors by a target hopping approach from p38α MAPK inhibitor templates. On the basis of an iterative approach of docking, compound preparation, biological testing, and SAR interpretation, robust and flexible synthetic routes were established. As a result, we report two reversible inhibitors 11d and 11e of the clinically challenging triple mutant L858R/T790M/C797S with IC50 values in the low nanomolar range. Furthermore, we developed a kinome selective irreversible inhibitor 45a with an IC50 value of 1 nM against the EGFR L858R/T790M double mutant. Target binding kinetics and metabolic stability data are included. These potent mutant EGFR inhibitors may serve as a basis for the development of structurally novel EGFR probes, tools, or candidates.
- Juchum, Michael,Günther, Marcel,D?ring, Eva,Sievers-Engler, Adrian,L?mmerhofer, Michael,Laufer, Stefan
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supporting information
p. 4636 - 4656
(2017/06/13)
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- Cooperative duplex formation by synthetic H-bonding oligomers
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A series of flexible oligomers equipped with phenol H-bond donors and phosphine oxide H-bond acceptors have been synthesised using reductive amination chemistry. H-bonding interactions between complementary oligomers leads to the formation of double-stranded complexes which were characterised using NMR titrations and thermal denaturation experiments. The stability of the duplex increases by one order of magnitude for every H-bonding group added to the chain. Similarly, the enthalpy change for duplex assembly and the melting temperature for duplex denaturation both increase with increasing chain length. These observations indicate that H-bond formation along the oligomers is cooperative despite the flexible backbone, and the effective molarity for intramolecular H-bond formation (14 mM) is sufficient to propagate the formation of longer duplexes using this approach. The product K EM, which is used to quantify chelate cooperativity is 5, which means that each H-bond is more than 80% populated in the assembled duplex. The modular design of these oligomers represents a general strategy for the design of synthetic information molecules that could potentially encode and replicate chemical information in the same way as nucleic acids.
- Stross, Alexander E.,Iadevaia, Giulia,Hunter, Christopher A.
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- Concise Asymmetric Construction of C2-symmetric 1,9-Diarylnonanoids Using a Hypervalent Silicon Complex: Total Synthesis of (-)-Ericanone
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By using a phosphine oxide-catalyzed enantioselective double aldol reaction, we achieved the concise construction of C2-symmetric 1,9-diarylnonanoids, enabling the synthesis of (-)-ericanone from p-hydroxybenzaldehyde in 6 steps with 65 % overall yield. The enantioselective double aldol reaction is useful for establishing C2-symmetric 1,9-diaryl-3,7-dihydroxy-5-nonanones with a single operation. Furthermore, the use of o-nosyl-protected p-hydroxybenzaldehyde and a 4,4′-disubstituted BINAP dioxide catalyst dramatically improved the reactivity and selectivity in the double aldol reaction, enabling the total synthesis of (-)-ericanone with high yield and with excellent enantiopurity.
- Kotani, Shunsuke,Kai, Kosuke,Shimoda, Yasushi,Hu, Hao,Gao, Shen,Sugiura, Masaharu,Ogasawara, Masamichi,Nakajima, Makoto
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supporting information
p. 376 - 379
(2016/05/19)
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- Decarboxylative Csp3-Csp3 coupling for benzylation of unstable ketone enolates: Synthesis of: P -(acylethyl)phenols
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A new decarboxylative Csp3-Csp3 coupling approach for the benzylation of ketone enolates has been developed. A variety of raspberry ketone derivatives were conveniently synthesized in good to excellent yields under mild conditions. A crossover reaction shed light on the mechanism of this tandem reaction.
- Wang, Sasa,Chen, Xinzheng,Ao, Qiaoqiao,Wang, Huifei,Zhai, Hongbin
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supporting information
p. 9454 - 9457
(2016/07/29)
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- Method of manufacturing calbonyl compd.
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PROBLEM TO BE SOLVED: To provide a method of manufacturing a carbonyl compound by smoothly performing a dehydrogenation reaction while preventing side reactions.SOLUTION: A method of manufacturing a carbonyl compound includes a process of converting alcohol to aldehyde or ketone by irradiating visible light to a reaction system containing a primary alcohol or a secondary alcohol, SrTiOcarrying a Ru atom and doped with Rh atom, and water.
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Paragraph 0051; 0052
(2018/06/30)
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- 4-(Pyren-1-ylimino)methylphenol and its silylated derivative as chromogenic chemosensors highly selective for fluoride or cyanide
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Two novel compounds, 4-(pyren-1-ylimino)methylphenol and 4-[(triisopropylsilyl)oxy] phenylmethylenepyren-1-amine) were synthesized. Solutions of 4-(pyren-1-ylimino)methylphenol in dimethyl sulfoxide (DMSO) are colorless, but on addition of cyanide and fluoride they become colored due to the deprotonation of the chemosensor. The system is highly selective toward cyanide with the addition of water. This compound can be solubilized in water with addition of cetyltrimethylammonium bromide above its critical micellar concentration. The pKa of the compound in water was determined as 10.49 ± 0.02 and this value is lowered in micellar medium to 7.49 ± 0.02, which means that only cyanide is sufficiently basic to achieve the deprotonation of the compound. Solutions of 4-[(triisopropylsilyl)oxy]phenylmethylenepyren-1-amine) in DMSO are colorless, but they are colored in the presence of cyanide and fluoride and only cyanide could be detected in DMSO-water mixture. The nucleophilic attack of the anions on the silicon center of the compound releases colored 4-(pyren-1-ylimino)methylphenolate, enabling the detection of nucleophilic analytes.
- Buske, Jonatan L. O.,Nicoleti, Celso R.,Cavallaro, Aluisio A.,Machado, Vanderlei G.
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p. 2507 - 2519
(2016/02/23)
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- The fight against the influenza A virus H1N1: Synthesis, molecular modeling, and biological evaluation of benzofurazan derivatives as viral RNA polymerase inhibitors
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The influenza RNA polymerase complex, which consists of the three subunits PA, PB1, and PB2, is a promising target for the development of new antiviral drugs. A large library of benzofurazan compounds was synthesized and assayed against influenza virus A/WSN/33 (H1N1). Most of the new derivatives were found to act by inhibiting the viral RNA polymerase complex through disruption of the complex formed between subunits PA and PB1. Docking studies were also performed to elucidate the binding mode of benzofurazans within the PB1 binding site in PA and to identify amino acids involved in their mechanism of action. The predicted binding pose is fully consistent with the biological data and lays the foundation for the rational development of more effective PA-PB1 inhibitors. In the fight against influenza virus A/WSN/33 (H1N1), the PA-PB1 protein-protein interaction is emerging as a new drug target. To identify small molecules able to inhibit the viral RNA polymerase complex, the benzofurazan scaffold was explored by synthesizing a large library of derivatives. Some compounds showed high anti-H1N1 activity and emerged as effective inhibitors of the PA-PB1 interaction, with IC50 values in the micromolar range. Copyright
- Pagano, Mafalda,Castagnolo, Daniele,Bernardini, Martina,Fallacara, Anna Lucia,Laurenzana, Ilaria,Deodato, Davide,Kessler, Ulrich,Pilger, Beatrice,Stergiou, Lilli,Strunze, Stephan,Tintori, Cristina,Botta, Maurizio
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p. 129 - 150
(2014/01/17)
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- Scalable asymmetric total syntheses of (+)-psoracorylifol B and (+)-ent-psoracorylifol C
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The first, asymmetric total syntheses of potent antimicrobial Psoracorylifol B (>1.3 g obtained, dr 10.5:1) with a 9.4% overall yield on a gram scale in 14 steps and ent-Psoracorylifol C with a 4.3% yield in 16 steps were achieved. The key features of our synthesis include (i) sequential, rarely explored Achmatowicz rearrangement/bicycloketalization to construct the 6,8-dioxabicyclo[3.2.1]octane core, and (ii) Cu-mediated SN2′ methylation or Johnson-Claisen rearrangement to stereoselectively install the all-carbon quaternary stereocenter. This concise, highly efficient, and scalable synthetic route may provide expedited and practical access to psoracorylifols and their analogues for further biological activity evaluation.
- Ren, Jingyun,Liu, Yuan,Song, Liyan,Tong, Rongbiao
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supporting information
p. 2986 - 2989
(2014/06/23)
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- Selective chromo-fluorogenic detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) with a unique probe based on a boron dipyrromethene (BODIPY) dye
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A novel colorimetric probe (P4) for the selective di fferential detection of DFP (a Sarin and Soman mimic) and DCNP (a Tabun mimic) was prepared. Probe P4 contains three reactive sites; i.e. (i) a nucleophilic phenol group able to undergo phosphorylation with nerve gases, (ii) a carbonyl group as a reactive site for cyanide; and (iii) a triisopropylsilyl (TIPS) protecting group that is known to react with fluoride. The reaction of P4 with DCNP in acetonitrile resulted in both the phosphorylation of the phenoxy group and the release of cyanide, which was able to react with the carbonyl group of P4 to produce a colour modulation from pink to orange. In contrast, phosphorylation of P4 with DFP in acetonitrile released fluoride that hydrolysed the TIPS group in P4 to yield a colour change from pink to blue. Probe P4 was able to discriminate between DFP and DCNP with remarkable sensitivity; limits of detection of 0.36 and 0.40 ppm for DCNP and DFP, respectively, were calculated. Besides, no interference from other organophosphorous derivatives or with presence of acid was observed. The sensing behaviour of P4 was also retained when incorporated into silica gel plates or onto polyethylene oxide membranes, which allowed the development of simple test strips for the colorimetric detection of DCNP and DFP in the vapour phase. P4 is the first probe capable of colorimetrically differentiating between a Tabun mimic (DCNP) and a Sarin and Soman mimic (DFP).
- Barba-Bon, Andrea,Costero, Ana M.,Gil, Salvador,Martnez-Mez, Ramn,Sancenn, Felix
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p. 8745 - 8751
(2015/02/19)
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- Total synthesis and configurational assignment of chondramide A
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The first total synthesis of the cyclodepsipeptide chondramide A (2b) is described. This depsipeptide is composed of four subunits, namely Lalanine, N-Me-D-tryptophan, 3-amino-2-methoxy-propionic acid (β-tyrosine derivative), and a 7-hydroxy-alkenoic acid. While the configuration of the stereogenic centers in the 7-hydroxy-alkenoic acid were known, the configuration of the tyrosine derivative required clarification and turned out to be (2S,3R) or (2L,3L), respectively. The synthesis of the 3-amino-2-methoxy-3-arylpropanoic ester 20 b relied on an asymmetric dihydroxylation yielding diol ent-15a followed by a regioselective Mitsunobu substitution leading to 3-azido-2-hydroxypropanoate 18 b. We could also show that the ester bond in the seco compound 26b can be fashioned by a Mitsunobu esterification by using hydroxy ester (7S)-7 and the tripeptide acid 25 b. This synthesis should allow for the preparation of various analogues.
- Schmauder, Anke,Sibley, L.David,Maier, Martin E.
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experimental part
p. 4328 - 4336
(2010/07/02)
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- Cycloadditions by oxidative visible light photocatalysis
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Photochemical reactions are remarkable for their ability to easily assemble cyclobutanes and other strained ring systems that are difficult to construct using other conventional synthetic methods. We have previously shown that Ru(bpy)32+ is an efficient photocatalyst that promotes the [2+2] cycloadditions of electron-deficient olefins with visible light. Here, we show that Ru(bpy)32+ is also an effective photocatalyst for the [2+2] cycloaddition of electron-rich olefins. This transformation is enabled by the versatile photoelectrochemical properties of Ru(bpy) 32+, which enables either one-electron reduction or one-electron oxidation of interesting organic substrates under appropriate conditions.
- Ischay, Michael A.,Lu, Zhan,Yoon, Tehshik P.
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supporting information; experimental part
p. 8572 - 8574
(2010/08/06)
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- PYRIPYROPENE DERIVATIVE HAVING ACAT2-INHIBITING ACTIVITY
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The present invention is a compound having the general formula (I), (II), or (III) or a pharmacologically acceptable salt, solvate, or hydrate thereof, and a pharmaceutical composition containing such a compound, or its pharmacologically acceptable ester, or other pharmacologically acceptable derivative thereof as an active ingredient. The compound has an excellent ACAT 2-inihibiting activity by a mechanism different from that of a statin drug and is useful as a therapeutic or prophylactic agent for obesity, adiposis, hyperlipidemia, hypercholesterolemia, disorder of lipid metabolism, and arteriosclerosis, as well as obesity-derived hyperlipidemia, hypercholesterolemia, disorder of lipid metabolism, arteriosclerosis, and hypertension.
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Page/Page column 25
(2010/10/01)
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- TRANS-1,2-DIPHENYLETHLENE DERIVATIVES AND NANOSENSORS MADE THEREFROM
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Novel trans-1,2-diphenylethylene derivatives are synthesized which can be used to form nanoparticles-monomer-nanomolecule-receptor nanosensors. These trans-1,2-diphenyl-ethylene derivatives are soluble in both water and organic solvents, highly fluorescent and can be synthesized in high yields. The trans-1,2-diphenylethylene derivatives are bonded to a nanoparticle, a nanomolecule bonded to the derivative and a receptor bonded to the nanomolecule to form a nanosensor that can be used to detect chemical and biological agents.
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- TRANS-1,2-DIPHENYLETHYLENE DERIVATIVES AND NANOSENSORS MADE THEREFROM
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Novel trans-1, 2-diphenylethylene derivatives are synthesized which can be used to form nanoparticles-monomer- nanomolecule-receptor nanosensors. These trans-1, 2-diphenyl- ethylene derivatives are soluble in both water and organic solvents, highly fluore
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Page/Page column 6
(2009/03/07)
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- Kinetics of self-immolation: Faster signal relay over a longer linear distance?
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A counterintuitive observation of a faster signal relay over a longer linear distance prompted detailed kinetic studies of self-immolation reactions. With appropriate conformational bias, trigger-to-reporter signal transduction can take an efficient "shor
- Lee, Ho Yong,Jiang, Xuan,Lee, Dongwhan
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supporting information; experimental part
p. 2065 - 2068
(2009/10/10)
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- Enantioselective total synthesis of (+)-jasplakinolide
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An enantioselective total synthesis of (+)-jasplakinolide is described. The synthesis of the polyketide template utilized a diastereoselective syn-aldol, ortho-ester Claisen rearrangement followed by efficient conversion to a cyanide. The β-amino acid uni
- Ghosh Deuk Kyu Moon, Arun K.
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p. 2425 - 2427
(2008/02/07)
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- An effective method for the synthesis of 13C-labeled polyprenylhydroxybenzoic acids
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The synthesis of side-chain 13C-labeled geranylgeranyl-4- hydroxybenzoic acids and geranylgeranyl-3,4-dihydroxybenzoic acids is described. The synthesis starts from O-protected methyl hydroxyiodobenzoates, which are transformed into Grignard re
- Lang, Martin,Steglich, Wolfgang
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p. 1019 - 1027
(2007/10/03)
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- From solution-phase to solid-phase enyne metathesis: Crossover in the relative performance of two commonly used ruthenium pre-catalysts
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A crossover in the ability of two distinct ruthenium-based metathesis pre-catalysts to effect the synthesis of dialkenylboronic esters in solution and on the solid-phase was observed. Specifically, while the Grubbs 2nd generation pre-catalyst 3 affords a
- Brittain, Dominic E.A.,Lawrence Gray,Schreiber, Stuart L.
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p. 5086 - 5093
(2007/10/03)
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- Synthetic approaches to the southern part of cyclotheonamide C
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A synthetic equivalent of the southern segment of cyclotheonamide C, a cyclopentapeptide isolated from the sponge Theonella, has been synthesized via complementary Wadsworth-Emmons or palladium-catalysed methodologies followed by tandem oxidation/vinyloga
- Aitken, David J.,Faure, Sophie,Roche, Stéphane
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p. 8827 - 8830
(2007/10/03)
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