Barcelona Science Park

Barcelona, Spain

Barcelona Science Park

Barcelona, Spain
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Vazquez-Romero A.,Barcelona Science Park | Kielland N.,Barcelona Science Park | Arevalo M.J.,University of Extremadura | Preciado S.,Barcelona Science Park | And 5 more authors.
Journal of the American Chemical Society | Year: 2013

Multicomponent reactions are excellent tools to generate complex structures with broad chemical diversity and fluorescent properties. Herein we describe the adaptation of the fluorescent BODIPY scaffold to multicomponent reaction chemistry with the synthesis of BODIPY adducts with high fluorescence quantum yields and good cell permeability. From this library we identified one BODIPY derivative (PhagoGreen) as a low-pH sensing fluorescent probe that enabled imaging of phagosomal acidification in activated macrophages. The fluorescence emission of PhagoGreen was proportional to the degree of activation of macrophages and could be specifically blocked by bafilomycin A, an inhibitor of phagosomal acidification. PhagoGreen does not impair the normal functions of macrophages and can be used to image phagocytic macrophages in vivo. © 2013 American Chemical Society.


Kielland N.,Barcelona Science Park | Vicente-Garcia E.,Barcelona Science Park | Reves M.,Barcelona Science Park | Isambert N.,Barcelona Science Park | And 3 more authors.
Advanced Synthesis and Catalysis | Year: 2013

A recently described family of multicomponent reactions (MCRs) involving isocyanides, aldehydes, dipolarophiles and alkylboranes that yield highly substituted aziridines, oxazolidines and pyrrolidines has been studied in detail. In this work the scope of these processes is significantly increased by preparing the borane input through hydroboration of alkenes or organometallic processes, in tandem with the MCR. The aldehyde range is also expanded, and indole-3-carbaldehydes yield reactive imines and bis-indolyloxazolidines, depending on the electron density of the heterocycle. Finally, the obtained adducts constitute an ideal platform to generate structurally diverse compounds using simple post-condensation modifications. In this way, indole imines undergo stereoselective hydrocyanation and oxazolidines are reductively opened to give amino alcohols. Additionally, palladium-, ruthenium- and gold-catalyzed processes lead to a variety of complex heterocycles. The methodology is simple, efficient and highly divergent, leading to an array of interesting scaffolds for medicinal chemistry. Copyright © 2013 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Vicente-Garcia E.,Barcelona Science Park | Ramon R.,Barcelona Science Park | Lavilla R.,Barcelona Science Park | Lavilla R.,University of Barcelona
Synthesis | Year: 2011

Oxa-, thia- and imidazolones are reactive inputs as electron-rich olefin components in Povarov reactions. On interaction with anilines and aldehydes, these substrates afford the corresponding multicomponent adducts in a regioselective manner. Intramolecular processes are also explored. Post-condensation oxidation provides convenient access to a variety of fused quinoline derivatives. © Georg Thieme Verlag Stuttgart • New York.


Gomez L.,Bioglane SLNE | Molinar-Toribio E.,CSIC - Institute of Advanced Chemistry of Catalonia | Calvo-Torras M.A.,Autonomous University of Barcelona | Adelantado C.,Autonomous University of Barcelona | And 7 more authors.
British Journal of Nutrition | Year: 2012

d-Fagomine is an iminosugar originally isolated from seeds of buckwheat (Fagopyrum sculentum Moench), present in the human diet and now available as a pure crystalline product. We tested d-fagomine for activities connected to a reduction in the risk of developing insulin resistance, becoming overweight and suffering from an excess of potentially pathogenic bacteria. The activities were: intestinal sucrase inhibition in vitro (rat mucosa and everted intestine sleeves), modulation of postprandial blood glucose in rats, bacterial agglutination and bacterial adhesion to pig intestinal mucosa. When ingested together with sucrose or starch, d-fagomine lowered blood glucose in a dose-dependent manner without stimulating insulin secretion. d-Fagomine reduced the area under the curve (0-120 min) by 20 % (P < 0•01) and shifted the time to maximum blood glucose concentration (T max) by 15 min at doses of 1-2 mg/kg body weight when administered together with 1 g sucrose/kg body weight. Moreover, d-fagomine (0•14 mm) agglutinated 60 % of Enterobacteriaceae (Escherichia coli, Salmonella enterica serovar Typhimurium) populations (P < 0•01), while it did not show this effect on Bifidobacterium spp. or Lactobacillus spp. At the same concentration, d-fagomine significantly (P < 0•001) inhibited the adhesion of Enterobacteriaceae (95-99 % cells in the supernatant) and promoted the adhesion of Lactobacillus acidophilus (56 % cells in the supernatant) to intestinal mucosa. d-Fagomine did not show any effect on bacterial cell viability. Based on all this evidence, d-fagomine may be used as a dietary ingredient or functional food component to reduce the health risks associated with an excessive intake of fast-digestible carbohydrates, or an excess of potentially pathogenic bacteria. © 2011 The Authors.


Preciado S.,Barcelona Science Park | Vicente-Garcia E.,Barcelona Science Park | Llabres S.,University of Barcelona | Luque F.J.,University of Barcelona | And 2 more authors.
Angewandte Chemie - International Edition | Year: 2012

When a door closes, a window opens! The use of geometrically or electronically restricted imines for Povarov-type processes does not afford the anti-Bredt tetrahydroquinolines, but leads instead to highly functionalized structures through novel reaction pathways (see picture; LA=Lewis acid). The exploration of "forbidden" routes constitutes a valuable approach in the search for new multicomponent reactions. Copyright © 2012 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Vicente-Garcia E.,Barcelona Science Park | Ramon R.,Barcelona Science Park | Preciado S.,Barcelona Science Park | Lavilla R.,Barcelona Science Park | Lavilla R.,University of Barcelona
Beilstein Journal of Organic Chemistry | Year: 2011

The tetrahydroquinolines obtained through the Povarov multicomponent reaction have been oxidized to the corresponding quino-line, giving access to a single product through a two-step sequence. Several oxidizing agents were studied and manganese dioxide proved to be the reagent of choice, affording higher yields, cleaner reactions and practical protocols. © 2011 Vicente-García et al.


Ghashghaei O.,University of Barcelona | Reves M.,University of Barcelona | Kielland N.,Barcelona Science Park | Lavilla R.,University of Barcelona
European Journal of Organic Chemistry | Year: 2015

Propargylamines, prepared through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. The key step of the mechanism involves the generation of an amidine intermediate, from the isocyanide insertion into the N-H bond of the propargylamine, which in situ evolves by cyclization upon the alkyne moiety. The scope of the process is analyzed and only shows restrictions for aliphatic amines, whereas it is quite general regarding the aldehyde, alkyne and isocyanide inputs. The protocol allows the preparation of a wide array of adducts, tandem one-pot processes being also feasible. Mechanistic studies using selected substrates have been used to determine the profile of the reaction and some substitution and functional group limitations. Some post-synthetic transformations of the imidazolium salts have been performed as well. Propargylamines, synthesized through A3-coupling of primary amines, aldehydes and terminal alkynes, react with isocyanides in an HCl-catalyzed process to yield tetrasubstituted imidazolium salts. Tandem one-pot protocols allow direct access to these adducts from the commercially available inputs. Copyright © 2015 WILEY-VCH Verlag GmbH & Co. KGaA, Weinheim.


Vicente-Garcia E.,Barcelona Science Park | Catti F.,Barcelona Science Park | Ramon R.,Barcelona Science Park | Lavilla R.,Barcelona Science Park | Lavilla R.,University of Barcelona
Organic Letters | Year: 2010

Unsaturated lactams with endo- or exocyclic C-C double bonds constitute a set of reactive inputs that serve as the electron-rich olefin component in Povarov reactions. These substrates afford the multicomponent adducts in convenient yields and offer a wide range of structural diversity. Postcondensation transformations allow direct access to a variety of lactam-fused and amide-substituted quinoline derivatives. © 2010 American Chemical Society.


Kielland N.,Barcelona Science Park | Catti F.,Barcelona Science Park | Bello D.,Barcelona Science Park | Isambert N.,Barcelona Science Park | And 4 more authors.
Chemistry - A European Journal | Year: 2010

New multicomponent reactions of aldehydes, isocyanides, trialkylboron reagents and dipolarophiles have been developed as an efficient route to diverse scaffolds, including aziridines, oxazolidines and poly-substituted pyrrolidines. This chemistry, inspired by a report by Hesse in 1965, is simple and involves mild conditions. Computational studies provide a basis to investigate the stereochemical features observed in the formation of oxazolidines and fourcomponent adducts, and permit identification of potential factors that might influence the outcome of the multicomponent reaction. Thus, a rational screening of all the components and reaction parameters is made to examine the manifold mechanistic pathways and establish the practical limits for standard applications. Finally, intramolecular and solid-supported versions of these reactions bring new synthetic possibilities and practical protocols. Overall, the results describe a new family of multicomponent reactions valuable not only for organic reactivity, but also for combinatorial chemistry and drug discovery. ©2010 Wiley-VCH Verlag GmbH & Cu. KGaA. Weinheim.


Gongora-Benitez M.,Barcelona Institute for Research in Biomedicine | Gongora-Benitez M.,CIBER ISCIII | Basso A.,Purolite International Ltd. | Bruckdorfer T.,IRIS Biotech GmbH | And 7 more authors.
Chemistry - A European Journal | Year: 2012

Enzyme-labile protecting groups have emerged as a green alternative to conventional protecting groups. These groups introduce a further orthogonal dimension and eco-friendliness into protection schemes for the synthesis of complex polyfunctional organic molecules. S-Phacm, a Cys-protecting group, can be easily removed by the action of a covalently immobilized PGA enzyme under very mild conditions. Herein, the versatility and reliability of an eco-friendly combination of the immobilized PGA enzyme and the S-Phacm protecting group has been evaluated for the synthesis of diverse Cys-containing peptides. © 2012 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim.

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