Todas las entradas de: Javier Carreras Pérez Aradros

2021, AzaBN, Publicación

Abengozar et al. Adv. Heterocycl. Chem.. 2021;:197-259. Recent developments in the chemistry of BN-aromatic hydrocarbons.

Publicaciones > Abengozar et al

Adv. Heterocycl. Chem. 2021 Mar 28; :197-259.

Recent developments in the chemistry of BN-aromatic hydrocarbons.

Alberto Abengozar, Patricia Garcia-Garcia, Manuel A. Fernández-Rodríguez, David Sucunza, Juan J Vaquero

Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá (IRYCIS), Campus Científico-Tecnológico, Facultad de Farmacia, Alcalá de Henares, Madrid, Spain.

Abstract

Heterocycles containing both N and B heteroatoms in their structure were first reported by Dewar in the middle of the last century. However, they received little attention until the early years of this century, when several groups revisited these compounds due to their interest in BN/CC isosterism. As a result of these systematic studies, very significant advances have been made in our understanding of the chemistry of these BN-heterocycles. The purpose of this review is to summarize the most significant advances in the last two decades as regards the development of synthetic strategies and studies of their reactivity, as well as to provide an overview of their general properties and main applications.

2021, BioImag, Publicación

Bosch et al. Dyes and Pigments. 2021;:109443. A new family of fluorescent pyridazinobenzimidazolium cations with DNA binding properties.

Publicaciones > Bosch et al

Dyes and Pigments. 2021 Aug 1; :109443. doi: 10.1016/j.dyepig.2021.109443

A new family of fluorescent pyridazinobenzimidazolium cations with DNA binding properties.

Pedro Bosch1, Gema Marcelo2, Alejandra Matamoros-Recio3, David Sucunza4, Francisco Mendicuti2, Alberto Domingo3, Juan J Vaquero4

1. Departamento de Química Orgánica y Química Inorgánica, Universidad de Alcalá, 28871, Alcalá de Henares, Madrid, Spain.  2. Departamento de Química Analítica, Química Física e Ingeniería Química, 28805, Alcalá de Henares, Madrid, Spain.  3. Departamento de Biología de Sistemas, Instituto de Investigación Química “Andrés M. Del Río” (IQAR), Universidad de Alcalá, IRYCIS, 28805, Alcalá de Henares, Madrid, Spain.  4. Departamento de Química Orgánica y Química Inorgánica, 28805, Alcalá de Henares, Madrid, Spain.

Abstract

A series of novel azonia aromatic heterocycles formed by a pyridazinobenzimidazolium system has been synthesized. Spectrofluorimetric and circular dichroism measurements, as well as theoretical simulations for these materials, have shown their interesting fluorescence properties and DNA-binding ability. Stoichiometries and binding constants were obtained by fluorescence and the induced circular dichroism spectra analysis. Moreover, the potential of these compounds for cell staining has been investigated in living HeLa cells by confocal microscopy imaging.

Noticias

Nuevo artículo, Dyes and Pigments 05.21

A new family of fluorescent pyridazinobenzimidazolium cations with DNA binding properties

Pedro Bosch, Gema Marcelo, Alejandra Matamoros-Recio, David Sucunza*, Francisco Mendicuti, Alberto Domingo, Juan J. Vaquero*

Dyes Pigm., 2021, In Press
DOI: 10.1016/j.dyepig.2021.109443

A series of novel azonia aromatic heterocycles formed by a pyridazinobenzimidazolium system has been synthesized. Spectrofluorimetric and circular dichroism measurements, as well as theoretical simulations for these materials, have shown their interesting fluorescence properties and DNA-binding ability. Stoichiometries and binding constants were obtained by fluorescence and the induced circular dichroism spectra analysis. Moreover, the potential of these compounds for cell staining has been investigated in living HeLa cells by confocal microscopy imaging.
2021, Publicación

Hervieu et al. Nat Chem. 2021;13(4):327-334. Asymmetric, visible light-mediated radical sulfinyl-Smiles rearrangement to access all-carbon quaternary stereocentres.

Publicaciones > article

Nat Chem. 2021 Apr;13(4):327-334. doi: 10.1038/s41557-021-00668-4. PubMed 33833448

Asymmetric, visible light-mediated radical sulfinyl-Smiles rearrangement to access all-carbon quaternary stereocentres.

Cédric Hervieu, Mariia Kirillova, Tatiana Suárez, Marco Müller, Estíbaliz Merino, Cristina Nevado

Abstract

The asymmetric construction of all-carbon quaternary centres within acyclic settings represents a long-standing challenge for synthetic chemists. Alongside polar and radical methods, rearrangement reactions represent an attractive platform, but still broadly applicable methods are in high demand. Here we report an asymmetric, radical sulfinyl-Smiles rearrangement to access acyclic amides that bear an α-all-carbon quaternary centre. Our strategy uses enantioenriched N-arylsulfinyl acrylamides as acceptors for a variety of radicals produced in situ under mild photoredox conditions. The sulfinamido group not only directs the 1,4-migration of the aryl moiety onto the α-carbon of the amide, which thus governs its absolute configuration, but also functions as a traceless chiral auxiliary. The amides obtained in this multicomponent process are prevalent in pharmaceuticals, agrochemicals and bioactive natural products, and can be transformed into valuable chiral α,α-disubstituted acids, oxindoles as well as into β,β-disubstituted amines, highlighting the synthetic potential of this transformation.

Noticias

Capítulo libro, Advances in Heterocyclic Chemistry 03.21

Recent developments in the chemistry of BN-aromatic hydrocarbons

Alberto Abengózar, Patricia García-García, Manuel A. Fernández-Rodríguez, David Sucunza*, Juan J. Vaquero*

Advances in Heterocyclic Chemistry, 2021, In Press, Corrected Proof
DOI: 10.1016/bs.aihch.2021.01.001

Versión final en abierto hasta el 21 de abril de 2021 en el siguiente enlace:
https://authors.elsevier.com/a/1cgCsErrnROHF

Heterocycles containing both N and B heteroatoms in their structure were first reported by Dewar in the middle of the last century. However, they received little attention until the early years of this century, when several groups revisited these compounds due to their interest in BN/CC isosterism. As a result of these systematic studies, very significant advances have been made in our understanding of the chemistry of these BN-heterocycles. The purpose of this review is to summarize the most significant advances in the last two decades as regards the development of synthetic strategies and studies of their reactivity, as well as to provide an overview of their general properties and main applications.
Noticias

Portadas 2020

Este año el grupo ha contribuido en dos de sus artículos en portadas de las revistas:

· Chem Med Chem
Pyrrolo[1,2‐a]quinoxalines: Insulin Mimetics that Exhibit Potent and Selective Inhibition against Protein Tyrosine Phosphatase 1B
Javier García‐Marín, Mercedes Griera, Patricia Sánchez‐Alonso, Bruno Di Geronimo, Francisco Mendicuti, Manuel Rodríguez‐Puyol*, Ramón Alajarín*, Beatriz de Pascual‐Teresa, Juan J. Vaquero*, Diego Rodríguez‐Puyol*

The Front Cover shows a C2C12 cell with the inhibitor 4‐benzylpyrrolo[1,2‐a]quinoxaline targeting the α3/α6/α7 tunnel in the Protein Tyrosine Phosphatase 1B (PTP1B) represented as a ribbon diagram. The insulin receptor (clear green) and the glucose transporter (clear yellow) shown at the cell membrane are involved in the glucose uptake by the cell. The inhibition of PTP1B by this molecule and their analogues produces an insulin mimetic effect. This is indicated by red arrows for the glucose molecules (in sticks) crossing the cell membrane to the cytosol.

· Org Lett
Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes
Ana Milián, Patricia García-García*, Adrián Pérez-Redondo, Roberto Sanz, Juan J. Vaquero, and Manuel A. Fernández-Rodríguez*

The cover art illustrates the solvent-controlled gold(I)-catalyzed selective synthesis of phenanthrenes and dihydrophenanthrenes from easily available biphenyl-embedded trienynes. Notably, the phenanthrene synthesis developed is complementary to the well-studied strategy that produces regioisomeric phenanthrenes, resulting from the competitive nucleophilic addition of biphenyl to the activated alkyne. In addition, the isolation of the cyclobutenyl derivative depicted in the figure accounts for the participation of cyclobutene species in the catalytic cycle.
2020, Au, Publicación

Milián et al. Org Lett. 2020;22(21):8464-8469. Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes.

Publicaciones > Milián et al

Org Lett. 2020 Nov 6;22(21):8464-8469. doi: 10.1021/acs.orglett.0c03067.

Selective Synthesis of Phenanthrenes and Dihydrophenanthrenes via Gold-Catalyzed Cycloisomerization of Biphenyl Embedded Trienynes.

Ana Milián1, Patricia García-García1, Adrián Pérez-Redondo1, Roberto Sanz2, Juan J Vaquero1, Manuel A Fernández-Rodríguez1

1. Departamento de Quı́mica Orgánica y Quı́mica Inorgánica, Instituto de Investigación Quı́mica "Andrés M. del Rı́o" (IQAR). Universidad de Alcalá (IRYCIS). Campus Cientı́fico-Tecnológico, Facultad de Farmacia, Autovía A-II, Km 33.1, 28805 Alcalá de Henares, Madrid, Spain.  2. Área de Quı́mica Orgánica, Departamento de Quı́mica, Facultad de Ciencias, Universidad de Burgos, Pza. Misael Bañuelos s/n, 09001 Burgos, Spain.

Abstract

Readily available o'-alkenyl-o-alkynylbiaryls, a particular type of 1,7-enynes, undergo a selective cycloisomerization reaction in the presence of a gold(I) catalyst to give interesting phenanthrene and dihydrophenanthrene derivatives in high yields. The solvent used provokes a switch in the evolution of the gold intermediate and plays a key role in the reaction outcome.

2020, Au, Publicación

Otarola et al. Catalysts. 2020;22(21):1178. Gold-Catalyzed Synthetic Strategies towards Four-Carbon Ring Systems.

Publicaciones > Otarola et al

Catalysts. 2020 Oct 8; 22(21):1178.

Gold-Catalyzed Synthetic Strategies towards Four-Carbon Ring Systems.

Guillermo G Otarola, Juan J Vaquero, Estíbaliz Merino, Manuel A Fernández-Rodríguez

Departamento de Quı́mica Orgánica y Quı́mica Inorgánica, Instituto de Investigación Quı́mica "Andrés M. del Rı́o" (IQAR). Universidad de Alcalá (IRYCIS). Campus Cientı́fico-Tecnológico, Facultad de Farmacia, Autovía A-II, Km 33.1, 28805 Alcalá de Henares, Madrid, Spain.

Abstract

Four carbon ring systems are frequently present in natural products with remarkable biological activities such as terpenoids, alkaloids, and steroids. The development of new strategies for the assembly of these structures in a rapid and efficient manner has attracted the interest of synthetic chemists for a long time. The current research is focused mainly on the development of synthetic methods that can be performed under mild reaction conditions with a high tolerance to functional groups. In recent years, gold complexes have turned into excellent candidates for this aim, owing to their high reactivity, and are thus capable of promoting a wide range of transformations under mild conditions. Their remarkable efficiency has been thoroughly demonstrated in the synthesis of complex organic molecules from simple starting materials. This review summarizes the main synthetic strategies described for gold-catalyzed four-carbon ring formation, as well as their application in the synthesis of natural products.

Noticias

Nuevo artículo, Catalysts 10.20

Gold-Catalyzed Synthetic Strategies towards Four-Carbon Ring Systems

Guillermo Otárola, Juan J. Vaquero, Estíbaliz Merino*, Manuel A. Fernández-Rodríguez*

Catalysts, 2020, Early View
DOI: 10.3390/catal10101178

Four carbon ring systems are frequently present in natural products with remarkable biological activities such as terpenoids, alkaloids, and steroids. The development of new strategies for the assembly of these structures in a rapid and efficient manner has attracted the interest of synthetic chemists for a long time. The current research is focused mainly on the development of synthetic methods that can be performed under mild reaction conditions with a high tolerance to functional groups. In recent years, gold complexes have turned into excellent candidates for this aim, owing to their high reactivity, and are thus capable of promoting a wide range of transformations under mild conditions. Their remarkable efficiency has been thoroughly demonstrated in the synthesis of complex organic molecules from simple starting materials. This review summarizes the main synthetic strategies described for gold-catalyzed four-carbon ring formation, as well as their application in the synthesis of natural products.