Category Archives: Publicación

2015, Publicación, TosMIC

Coppola et al. Org Lett. 2015;17(1):78-81. Isoquinoline synthesis by heterocyclization of tosylmethyl isocyanide derivatives: total synthesis of mansouramycin B.

Publications > Coppola et al

Org Lett. 2015, 17, 78 PubMed 25521281

Isoquinoline synthesis by heterocyclization of tosylmethyl isocyanide derivatives: total synthesis of mansouramycin B.

Anna Coppola, David Sucunza, Carolina Burgos, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala , 28871 Alcala de Henares, Madrid, Spain.

Abstract

A new method for the synthesis of isoquinolines through a catalytic acid-mediated cyclization of alpha-benzyl TosMIC derivatives has been developed. This methodology has been successfully applied to the total synthesis of mansouramycin B. This is the first total synthesis of this compound to be reported in the literature.

2015, BioImag, Publicación

Suarez et al. Org Biomol Chem. 2015;13(2):527-38. Targeting DNA with small molecules: a comparative study of a library of azonia aromatic chromophores.

Publications > Suarez et al

Org Biomol Chem. 2015, 13, 527 PubMed 25378061

Targeting DNA with small molecules: a comparative study of a library of azonia aromatic chromophores.

Rosa M Suareza, Pedro Bosch, David Sucunza, Ana M Cuadro, Alberto Domingo, Francisco Mendicuti, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala, 28871-Alcala de Henares, Madrid, Spain.

a. juanjose.vaquero@uah.es

Abstract

A library of azonia aromatic cations has been studied in order to gain insights into the effect of the size, shape and charge distribution on the fluorescence, DNA interactions and DNA sequence selectivity properties. Fluorescence-based thermal denaturation experiments, spectrofluorimetric titrations, circular dichroism measurements and theoretical simulations have shown that some of the studied chromophores have interesting fluorescence properties and two of them also show a consistent DNA-binding ability by intercalation, with a potential preference for AT-rich sequences.

2014, Publicación

Abarca et al. Org Lett. 2014;16(13):3464-7. Efficient synthesis of an indoloquinolizinium alkaloid selective DNA-binder by ring-closing metathesis.

Publications > Abarca et al

Org Lett. 2014, 16, 3464 PubMed 24940996

Efficient synthesis of an indoloquinolizinium alkaloid selective DNA-binder by ring-closing metathesis.

Beatriz Abarca, Raul Custodio, Ana M Cuadro, David Sucunza, Alberto Domingo, Francisco Mendicuti, Julio Alvarez-Builla, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, double daggerDepartamento de Biologia de Sistemas, section signDepartamento de Quimica Analitica, Quimica Fisica e Ingenieria Quimica, Universidad de Alcala , 28871-Alcala de Henares, Madrid, Spain.

Abstract

Two total syntheses of the indolo[2,3-a]quinolizinium cation have been accomplished through the application of two ring-closing metathesis reactions to form the pyridinium ring. One of these approaches provides the tetracyclic cation in only five steps from commercially available harmane. Fluorescence-based thermal denaturation experiments, as well as spectrofluorimetric titration, circular dichroism measurements, and theoretical simulations, showed a consistent DNA-binding capacity by intercalation with a marked preference for AT-rich sequences.

2014, Publicación

Sanchez et al. Org Biomol Chem. 2014;12(24):4233-42. Microwave-assisted synthesis of potent PDE7 inhibitors containing a thienopyrimidin-4-amine scaffold.

Publications > Sanchez et al

Org Biomol Chem. 2014, 12, 4233 PubMed 24838636

Microwave-assisted synthesis of potent PDE7 inhibitors containing a thienopyrimidin-4-amine scaffold.

Ana I Sanchez, Ricardo Meneses, Jose M Minguez, Araceli Nunez, Rafael R Castillo, Fabiana Filace, Carolina Burgos, Juan J Vaquero, Julio Alvarez-Builla, Alvaro Cortes-Cabrera, Federico Gago, Emma Terricabras, Victor Segarra

Departamento de Quimica Organica, Universidad de Alcala, E-28871 Alcala de Henares, Madrid, Spain. julio.alvarez.@uah.es.

Abstract

A series of novel thienopyrimidin-4-amines have been synthesized and evaluated as phosphodiesterase (PDE) inhibitors. A rationale for the observed selectivity against PDE7 has been obtained from molecular modelling studies on the most active compounds.

2014, Publicación

Carmona et al. Dyes and Pigments. 2014;:106-117. Cucurbit[n]urils as a potential fine-tuned instrument for modifying photophysical properties of D–π–A+–π–D “push–pull” chromophores.

Publications > Carmona et al

Dyes Pigm. 2014, 103, 106

Cucurbit[n]urils as a potential fine-tuned instrument for modifying photophysical properties of D–π–A+–π–D “push–pull” chromophores.

Thais Carmona1, Tatiana Cañeque2, Raul Custodio2, Ana M. Cuadro2, Juan J Vaquero2, Francisco Mendicuti1

1. Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain.  2. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain.

Abstract

Photophysical properties of supramolecular complexes between cucurbit[7]uril (CB[7]) and one- (1D, linear) and two-dimensional (2D, V-shaped) D–π–A+–π–D pyridinium (A+) based “push–pull” chromophores, were investigated by UV–Vis and fluorescence techniques, as well as Molecular Mechanics and Molecular Dynamics simulations. Both chromophores formed stable complexes with CB[7] of different stoichiometries. Complexation was accompanied by significant changes in the photophysical properties of the guests: (i) bathochromic shifts for the π–π* charge transfer absorption band, which is more evident for the 1D than for the V-shaped one, (ii) significant enhancement of the fluorescence intensity, (iii) displacement to the blue of the emission and (iv) change in their fluorescence lifetimes, which is more patent for the V-shaped one. 1D chromophore/CB[7] complex formation was both enthalpically and entropically favored, whereas inclusion of the V-shaped one, accompanied by a little positive enthalpy change, was entropically governed. Variation of fluorescence lifetime and fluorescence anisotropy upon complexation exhibited quite different behaviors. MM and MD calculations were performed to simulate the complexation processes in the presence of water, determine their preferred structures and establish the host:guest interactions responsible for the complexes formation which were preferentially electrostatics.

2014, Publicación

Cañeque et al. Dyes and Pigments. 2014;:116-121. Novel charged NLO chromophores based on quinolizinium acceptor units.

Publications > Cañeque et al

Dyes Pigm. 2014, 101, 116

Novel charged NLO chromophores based on quinolizinium acceptor units.

Tatiana Cañeque1, Ana M. Cuadro1, Julio Alvarez-Builla1, Julio Alvarez-Builla2, Javier Pérez-Moreno3, Koen Clays3, Obis Castaño4, José L. Andrés5, Juan J Vaquero1

1. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain.  2. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28871, Alcalá de Henares, Madrid, Spain.  3. Department of Chemistry, University of Leuven, Celestijnenlaan 200 D, B-3001, Belgium.  4. Departamento de Química Analítica, Química Física e Ingeniería Química, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain.  5. IES Matarraña, 44580 Valderrobres, Teruel, Spain.

Abstract

An azonia cation has been explored for the first time as an acceptor unit in charged π-donor π-acceptor chromophores. Initial experimental and theoretical data show that quinolizinium, the simplest heteroaromatic azonia cation, behaved as a good acceptor unit and conferred promising nonlinear optical properties to simple push–pull cationic chromophores.

2013, Publicación

Coppola et al. Org Lett. 2013;15(13):3388-91. Remote aryl cyanation via isocyanide-cyanide rearrangement on tosylmethyl isocyanide derivatives.

Publications > Coppola et al

Org Lett. 2013 Jul 5;15(13):3388-91. doi: 10.1021/ol401433x. Epub 2013 Jun 24. PubMed 23795915

Remote aryl cyanation via isocyanide-cyanide rearrangement on tosylmethyl isocyanide derivatives.

Anna Coppola, Patricia Sanchez-Alonso, David Sucunza, Carolina Burgos, Ramon Alajarin, Julio Alvarez-Builla, Marta E G Mosquera, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala, 28871 - Alcala de Henares, Madrid, Spain.

Abstract

The reaction of alkyl tosylmethyl isocyanides and 2-bromobenzyl bromides in the presence of t-BuLi gives rise to a cascade reaction to give unexpected 2-substituted 2,3-dihydro-1H-indenimines which, upon treatment with t-BuOK, rearrange to 2-vinylbenzonitriles in high overall yields. This simple procedure represents a new approach to the synthesis of aromatic nitriles via isocyanide-cyanide interconversion.

2013, Publicación

Ramirez et al. Organic and Biomolecular Chemistry. 2013;11(41):7145 -7154. Synthesis of charged bis-heteroaryl donor-acceptor (D-A+) NLO-phores coupling (π-deficient-π-excessive) heteroaromatic rings.

Publications > Ramirez et al

Organic and Biomolecular Chemistry. 2013; 11(41):7145 -7154.

Synthesis of charged bis-heteroaryl donor-acceptor (D-A+) NLO-phores coupling (π-deficient-π-excessive) heteroaromatic rings.

M.A. Ramirez1, 2, 3, 4, R. Custodio, A.M. Cuadro, J. Alvarez-Builla, K. Clays, I. Asselberghs, F. Mendicuti, O. Castaño, J.L. Andrés, J.J. Vaquero

1. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28871-Alcalá de Henares, Madrid, Spain.  2. Department of Chemistry, University of Leuven, Celestijnenlaan 200 D, 3001 Leuven, Belgium.  3. Departamento de Quimica Analitica, Quimica Fisica e Ingenieria Quimica, Universidad de Alcalá, 28871 Alcalá de Henares, Madrid, Spain.  4. IES Matarraña, 44580 Valderrobres, Teruel, Spain.

Resumen

Charged chromophores based on heteroaromatic cations were prepared by reaction of alkylazinium salts with N-heteroarylstannanes under Stille conditions. This approach provides easy access to potential single donor D-A+ chromophores in which the acceptor moiety A+ is the pyridinium cation and the donors are different π-excessive N-heterocycles. The β hyperpolarizabilities were measured in hyper-Rayleigh scattering experiments and the experimental data are supported by a theoretical analysis that combines a variety of computational procedures, including density functional theory and correlated Hartree-Fock-based methods. In some chromophores, the absence of a bridge between donor and acceptor fragments increases the NLO properties. © 2013 The Royal Society of Chemistry.

2013, Publicación

Todor-G.-Deligeorgiev et al. Continued as Current Materials Science. 2013;6(2):81 -119. Title

Publications > Todor-G.-Deligeorgiev et al

Continued as Current Materials Science. 2013; 6(2):81 -119.

No hay título

Todor G. Deligeorgiev, Aleksey A. Vasilev, Stefka S. Kaloyanova and Juan-Jose Vaquero

Palabras clave: Biosensors; covalently binding dyes; DNA binders; fluorescent dyes; intercalation; non-covalently binding dyes; protein fluorescent probes.

Resumen

For life science research the fluorescent probes are essential tools and their use is continually increasing due to

2013, Publicación

Sánchez et al. Bioorg. Med. Chem.. 2013;21(8):2370 -2378. Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors.

Publications > Sánchez et al

Bioorg. Med. Chem. 2013; 21(8):2370 -2378.

Synthesis and evaluation of quinazoline derivatives as phosphodiesterase 7 inhibitors.

A.I. Sánchez1, V. Martínez-Barrasa2, C. Burgos3, J.J. Vaquero4, J. Alvarez-Builla, E. Terricabras, V. Segarra

1. Departamento de Quimica Orgánica, Universidad de Alcala, 28871 Alcalá de Henares, Madrid, Spain.  2. Almirall-Prodesfarma, Laureà Miró 408-410, 08980 Sant Felíu de Llobregat, Barcelona, Spain.  3. Centro Nacional de Referencia Sobre Contaminantes Orgánicos Persistentes (CNRCOP), Parque Científico Tecnológico, Universidad de Alcalá, C/Punto Net, 4, 28871 Alcalá de Henares, Madrid, Spain.  4. Pharma Mar S.A., Avda. De los Reyes, 1 Pol. Ind. La Mina-Norte, 28770 Colmenar Viejo, Madrid, Spain.

Resumen

The latest scientific findings concerning PDE7 and PDE4 inhibition suggest that selective small-molecule inhibitors of both enzymes could provide a novel approach to treat a variety of immunological diseases. In this context, we describe a new series of quinazoline derivatives from quinazolin-4-thiones which include a substituted biphenyl fragment. Some of these compounds show inhibitory potencies at sub-micromolar levels against the catalytic domain of PDE7. © 2013 Elsevier Ltd. All rights reserved.