- Magnolol dimer-derived fragments as PPARγ-selective probes
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Partial agonists of the transcription factor PPARγ (peroxisome proliferator-activated receptor γ) have shown potential for the treatment of metabolic and inflammatory conditions and novel activators serve as valuable tool and lead compounds. Based on the
- Dreier, Dominik,Resetar, Mirta,Temml, Veronika,Rycek, Lukas,Kratena, Nicolas,Schnürch, Michael,Schuster, Daniela,Dirsch, Verena M.,Mihovilovic, Marko D.
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Read Online
- Design, synthesis, and biological evaluation of novel dual FFA1 and PPARδ agonists possessing phenoxyacetic acid scaffold
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The free fatty acid receptor 1 (FFA1/GPR40) and peroxisome proliferator-activated receptor δ (PPARδ) have been widely considered as promising targets for type 2 diabetes mellitus (T2DM) due to their respective roles in promoting insulin secretion and impr
- Zhou, Zongtao,Cai, Zongyu,Zhang, Congzi,Yang, Benhui,Chen, Lianru,He, Yepu,Zhang, Luyong,Li, Zheng
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- ENANTIOPURE TERPHENYLS WITH TWO ORTHO-ATROPISOMERIC AXES
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Enantiopure terphenyl presenting two ortho-located chiral axes having the following structural formula (I) : their process of synthesis and their use as mono or bidentate ligands for asymmetric organometallic reactions, as organocatalysts, as chiral base
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Page/Page column 18-19
(2019/07/19)
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- Two Stereoinduction Events in One C?H Activation Step: A Route towards Terphenyl Ligands with Two Atropisomeric Axes
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Herein we disclose the synthesis of original chiral scaffolds—ortho-orientated terphenyls presenting two atropisomeric Ar–Ar axes. These unusual structures were built up by using the C?H activation approach, and remarkably, both chiral axes were controlled with excellent stereoselectivity in a single transformation. During the reaction, not only does atroposelective functionalization of a biaryl precursor occur to establish one stereogenic axis, but an unprecedented atropo-stereoselective C?H arylation also takes place to generate the second stereogenic element. These enantiomerically pure ortho-terphenyls show an original tridimensional structure and thus constitute a unique foundation for building up a library of enantiomerically pure bidentate ligands, such as the new ligands S/N-Biax and diphosphine BiaxPhos.
- Dherbassy, Quentin,Djukic, Jean-Pierre,Wencel-Delord, Joanna,Colobert, Fran?oise
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supporting information
p. 4668 - 4672
(2018/03/21)
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- Fast and Tight Boronate Formation for Click Bioorthogonal Conjugation
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A new click bioorthogonal reaction system was devised to enable the fast ligation (kON≈340 m-1 s-1) of conjugatable derivatives of a rigid cyclic diol (nopoldiol) and a carefully optimized boronic acid partner, 2-methyl-5-carboxymethylphenylboronic acid. Using NMR and fluorescence spectroscopy studies, the corresponding boronates were found to form reversibly within minutes at low micromolar concentration in water, providing submicromolar equilibrium constant (Keq≈105-106 m-1). Efficient protein conjugation under physiological conditions was demonstrated with model proteins thioredoxin and albumin, and characterized by mass spectrometry and gel electrophoresis.
- Akgun, Burcin,Hall, Dennis G.
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supporting information
p. 3909 - 3913
(2016/03/19)
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- THIADIAZOLE SUBSTITUTED COUMARIN DERIVATIVES AND THEIR USE AS LEUKOTRIENE BIOSYNTHESIS INHIBITOR
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The instant invention provides compounds of Formula (Ia) which are leukotriene biosynthesis inhibitors, wherein X is O or S, Y is O, S, -NR6-CHR7- or -NR8-C(O)- and A is selected from 5-membered aromatic heterocyclic ring, 6-membered aromatic heterocyclic ring, naphthelenic or heterobicyclic aromatic ring system, phenyl and benzyl. A is optionally mono- or disubstituted. Compounds of Formula (Ia) are useful as anti-atherosclerotic, anti-asthmatic, anti-allergic, anti-inflammatory and cytoprotective agents.
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Page/Page column 33
(2008/06/13)
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- Electronic effects of ring substituents on triplet benzylic biradicals
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UV irradiation of α-(o-alkylphenyl)acetophenones with a methoxy or cyano substituent para to the o-alkyl group of the α-aryl ring has revealed that a methoxy group slightly increases the stereoselectivity but not the quantum yield of indanol formation, whereas a cyano group greatly lowers both diastereoselectivity and quantum efficiency, confirming the likelihood that hydrogen-bonding of the hydroxy group to the α-phenyl ring plays an important role in the cyclization of the photogenerated triplet 1,5-biradical intermediates.
- Wagner, Peter J.,Wang, Lingling
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p. 645 - 647
(2007/10/03)
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- A simple and regioselective α-bromination of alkyl aromatic compounds by two-phase electrolysis
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Electrochemical bromination of toluene and substituted toluenes by two-phase electrolysis yields the corresponding α-brominated products. The reaction has been carried out in a single compartment cell with platinum electrodes at 0°C in chloroform using an aqueous sodium bromide solution (60%) containing a catalytic amount of HBr. Two-phase electrolysis results in high yields (60-95%) of monobromo compounds with very high regioselectivity (>95%).
- Raju,Kulangiappar,Anbu Kulandainathan,Muthukumaran
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p. 7047 - 7050
(2007/10/03)
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- Benzotriazine inhibitors of kinases
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The invention provides benzotriazine compounds having formula (I). The benzotriazine compounds of the invention are capable of inhibiting kinases, such members of the Src kinase family, and various other specific receptor and non-receptor kinases.
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Page/Page column 98
(2008/06/13)
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- Some evidence in favour of an electron transfer mechanism in the TiO2 photosensitized oxidation of benzyl derivatives in aqueous media
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The structure and/or distribution of products from the TiO2-sensitized photooxidation of some benzyl derivatives in aerated and/or deaerated aqueous media and in the presence of Ag2SO4 are reported. The results suggest that the single electron transfer process from the substrate to the photogenerated hole, previously proposed in CH3CN, should also be operative on gradually going from aqueous CH3CN to pure water.
- Ranchella, Michele,Rol, Cesare,Sebastiani, Giovanni V.
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p. 311 - 315
(2007/10/03)
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- Collisionally induced dissociation in the study of A-ring hydroxylated vitamin D type compounds
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Colllslonally Induced dissociation (CID) is often used to determine the structure of ions based on comparison with the CID spectra of known ions. The latter are generated from Judiciously selected compounds taking into account basic principles of Ion chemistry. We report here on the use of this approach toward determination of the site of A-ring hydroxylation of vitamin D. Although not Intrinsically an aromatic compound, vitamin D gives rise in its mass spectrum to an aromatic methytstyryl cation at mlz 118. A-ring hydroxylated metabolites of vitamin D would thus Incorporate the extra OH group on the ion at mlz 118, shifting it to mlz 134. The position of substitution of the extra OH group on a metabolite could then be ascertained by comparing the CID spectrum of its mlz 134 fragment to those of the four possible (hydroxymethyl)styryl cations generated from synthesized authentic compounds. Because of their propensity to polymerize, these cations were generated in situ via the McLafferty rearrangement of the corresponding (hydroxyphenyl)ethanols. For optimum differentiation of Isomeric Ions, preparation of permethylated derivatives of vitamin D was necessary. The validity of the hypothesis was verified using 1,25-dihydroxy-vitamin D3 as a test compound. This method provides a viable approach for the characterization of A-ring hydroxylated metabolites of vitamin D as well as for related aromatic compounds.
- Young, David C.,Vouros, Paul,Holick, Michael F.,Higuchi, Tetsuo
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p. 837 - 842
(2007/10/02)
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- ELECTROPHILIC BROMINATION OF PHENOL ETHERS IN SUPERACID SOLUTION USING ALKALI BROMIDE
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Electrophilic aromatic bromination of phenol ethers in superacid medium can be achieved with sodium or potassium bromide. The yield and selectivity are lower than with bromine, the oxidation of the halide to the electrophilic halogen cation is obtained by concomitant reduction of antimony pentafluoride. Selectivity is observed only in methylanisole.
- Cherry, Ghassan,Culmann, Jean-Christophe,Sommer, Jean
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p. 2007 - 2010
(2007/10/02)
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- Halogenation of benzyl- and (heteroaromatic methyl)cobaloximes: Direct competition between ring halogenation and cobalt-carbon bond cleavage
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(4-Acetamidobenzyl)- and (4-(dimethylamino)benzyl)cobaloximes react rapidly with low concentrations of chlorine and bromine in acetic acid or chloroform at room temperature under nitrogen. Both ring-halogenated organometallic products and direct Co-C cleavage products are formed. However, (4-methoxybenzyl)cobaloxime forms 4-methoxy-2-halotoluene as the exclusive product. (3-Methylbenzyl)cobaloxime undergoes a substantial proportion of ring substitution by both Br2 and Cl2 in competition with the cleavage of the Co-C bond. (3-Methoxybenzyl)cobaloxime forms only the ring-substituted organometallic product. A remarkable difference in reactivity between 2- and 3-isomers of the (thienylmethyl)- and (furylmethyl)cobaloximes is observed; for example, Co-C cleavage is the primary process in furfuryl- and (2-thienylmethyl)cobaloximes whereas ring halogenation occurs much faster in the 3-isomer. The results are discussed in terms of a σ-π delocalization phenomenon by which the electronic effect of a substituent in the benzyl group is effectively transmitted to the Co-C bond reactivity. The substituent effect of the metallomethyl group -CH2Co(dmgH)2py is found to be more than that of the methoxy group. The mechanism of the Co-C cleavage is described.
- Gupta,Kumar, Manoj,Roy, Sujit
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- Halogenolysis of Benzylcobaloximes
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The reaction of substituted benzylcobaloximes p-RC6H4Co(dmgH)2-Py (R=OMe, NHCOCH3 and NMe2) and m-RC6H4CH2Co(dmgH)2Py (R=Me, OMe) with halogens (Cl2 and Br2) in chloroform under nitrogen forms ring substituted organic and organometallic products.
- Gupta, B. D.,Kumar, Manoj
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p. 701 - 704
(2007/10/02)
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- MECHANISM OF ISOMERISATION OF ortho OR para BROMO PHENOLS IN SUPERACIDS
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In superacids ortho or para bromo phenols are isomerised into the meta bromo isomers.In SbF5-HF, the process is intramolecular and proceeds by a 1,2-Br shift.In CF3SO3H, the mechanism involves loss of bromine, followed by meta bromination.
- Jacquesy, Jean-Claude,Jouannetaud,Marie-Paule
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p. 1673 - 1676
(2007/10/02)
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