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Noticias

Org Lett 09.2020

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*

Org. Lett, 2020, ASAP
DOI: acs.orglett.0c03067

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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.
Miembros

Guillermo Otarola

Guillermo Otarola

  • FPI grant Universidad de Alcalá (2021-2024)
  • REDINREN associate researcher Universidad de Alcalá (2020)
  • Master Drug Discovery, Universidad de Alcalá (2019/2020)
  • Graduated at the Universidad de Alcalá (2019)

Publications in the group

Visible-Light-Mediated Regioselective Chlorosulfonylation of Acrylamides.
Mercedes Zurro, Sergio Torres-Oya, Guillermo G. Otárola, Juan José Vaquero, Estíbaliz Merino
Synthesis 2023, 55, 1783
Gold-catalyzed endo-selective cyclization of alkynylcyclobutanecarboxamides: synthesis of cyclobutane-fused dihydropyridones.
M Soledad Garre, Guillermo G Otárola, Estíbaliz Merino, David Sucunza, Enrique Aguilar, M Teresa Quirós, Juan J Vaquero, Patricia García-García
Org Biomol Chem. 2023, 21, 2705
Electrochemically driven one-pot oxidative conversion of arylhydrazines into aromatic iodides.
Noemi Salardón, Guillermo Otárola, Clara Mañas, Estíbaliz Merino, Belen Batanero
J. Environ. Chem. Eng. 2022, 10, 107486
Gold-Catalyzed Synthetic Strategies towards Four-Carbon Ring Systems.
Guillermo G Otarola, Juan J Vaquero, Estíbaliz Merino, Manuel A Fernández-Rodríguez
Catalysts 2020, 22, 1178
Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene.
Alberto Abengozar, Isabel Valencia, Guillermo G Otarola, David Sucunza, Patricia Garcia-Garcia, Adrian Perez-Redondo, Francisco Mendicuti, Juan J Vaquero
Chem Commun 2020, 56, 3669
Noticias

ChemMedChem 09.20

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*

ChemMedChem, 2020, Early View
DOI: 10.1002/cmdc.202000446

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PTP1B dephosphorylates insulin receptor and substrates to modulate glucose metabolism. This enzyme is a validated therapeutic target for type 2 diabetes, but no current drug candidates have completed clinical trials. Pyrrolo[1,2‐a]quinoxalines substituted at positions C1–C4 and/or C7–C8 were found to be nontoxic to cells and good inhibitors in the low‐ to sub‐micromolar range, with the 4‐benzyl derivative being the most potent inhibitor (0.24 μm). Some analogues bearing chlorine atoms at C7 and/or C8 kept potency and showed good selectivity compared to TCPTP (selectivity index >40). The most potent inhibitors behaved as insulin mimetics by increasing glucose uptake. The 4‐benzyl derivative inhibited insulin receptor substrate 1 and AKT phosphorylation. Molecular docking and molecular dynamics simulations supported a putative binding mode for these compounds to the allosteric α3/α6/α7 pocket, but inconsistent results in enzyme inhibition kinetics were obtained due to the high tendency of these inhibitors to form stable aggregates. Computational calculations supported the druggability of inhibitors.
2020, Publicación

Altarejos et al. Eur J Org Chem. 2020:3024-3029. Practical Solvent-Free Microwave-Assisted Hydroboration of Alkynes

Publications > Altarejos et al

Eur. J. Org. Chem. 2020, 3024

Practical Solvent-Free Microwave-Assisted Hydroboration of Alkynes.

Julia Altarejos, David Sucunza, Juan J Vaquero, Javier Carreras

Departamento de Química Orgánica y Química Inorgánica, Instituto de Investigación Química “Andrés M. del Río” (IQAR), Universidad de Alcalá, IRYCIS, 28805 Madrid, Alcalá de Henares, Spain.

. javier.carreras@uah.es

Abstract

A simple and rapid protocol for the anti-Markovnikov hydroboration of alkynes assisted by microwave irradiation has been developed. Pinacolborane smoothly reacts with terminal alkynes to obtain (E)-alkenyl boronates in good yields and short reactions times in the absence of solvent. Further transformations on the carbon-boron bond of the adducts can be sequentially achieved without the need of purifying the alkenyl boronates.

Noticias

EurJOC 04.2020

Practical solvent‐free microwave‐assisted hydroboration of alkynes

Julia Altarejos, David Sucunza, Juan José Vaquero, Javier Carreras*

Eur. J. Org. Chem., 2020, Accepted Articles
DOI: 10.1002/ejoc.202000110

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A simple and rapid protocol for the anti‐Markovnikov hydroboration of alkynes assisted by microwave irradiation has been developed. Pinacolborane smoothly reacts with terminal alkynes to obtain (E)‐alkenyl boronates in good yields and short reactions times in the absence of solvent. Further transformations on the carbon‐boron bond of the adducts can be sequentially achieved without the need of purifying the alkenyl boronates.
2020, AzaBN, Publicación

Abengozar et al. Chem Commun (Camb). 2020;56(25):3669-3672. Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene.

Publications > Abengozar et al

Chem Commun 2020, 56, 3669 PubMed 32115593

Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene.

Alberto Abengozara, Isabel Valencia, Guillermo G Otarola, David Sucunza, Patricia Garcia-Garcia, Adrian Perez-Redondo, Francisco Mendicuti, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR), Universidad de Alcala, IRYCIS, 28805 Alcala de Henares, Spain.

a. david.sucunza@uah.es, juanjose.vaquero@uah.es

Abstract

Previously unknown 4a-aza-12a-borachrysene has been synthesized in only four steps. The reactions of this BN-embedded PAH with bromine and organolithium compounds proceed with complete regioselectivity, resulting in the formation of nine derivatives. One of these, a phenylalkynyl-substituted derivative, exhibits a remarkably high fluorescence quantum yield (PhiF = 0.68).

Noticias

ChemComm 03.2020

Expanding the BN-embedded PAH family: 4a-aza-12a-borachrysene

Alberto Abengózar,‡ Isabel Valencia,‡ Guillermo G. Otárola, David Sucunza,* Patricia García-García, Adrián Pérez-Redondo, Francisco Mendicuti and Juan J. Vaquero*

Chem. Commun., 2020, Advance Article
DOI: 10.1039/C9CC09998K

Previously unknown 4a-aza-12a-borachrysene has been synthesized in only four steps. The reactions of this BN-embedded PAH with bromine and organolithium compounds proceed with complete regioselectivity, resulting in the formation of nine derivatives. One of these, a phenylalkynyl-substituted derivative, exhibits a remarkably high fluorescence quantum yield (ΦF = 0.68).

2020, BioImag, Publicación

Garre et al. J Org Chem. 2020;85(2):441-448. Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties.

Publications > Garre et al

J Org Chem. 2020, 85, 441 PubMed 31858801

Synthesis and Photophysical Behavior of a Highly Fluorescent Family of Unsymmetrical Organoboron Complexes Containing 5-(Pyridin-2-ylmethylene)imidazolidine-2,4-dione Moieties.

M Soledad Garre1, Raul Losantos2, Sara Gutierrez1, David Sucunza1, Patricia Garcia-Garcia1, Diego Sampedro2, Juan J Vaquero1

1. Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR) , Universidad de Alcala, IRYCIS , 28805 Alcala de Henares , Spain.  2. Departamento de Quimica, Centro de Investigacion en Sintesis Quimica (CISQ) , Universidad de La Rioja , Madre de Dios 53 , 26006 Logrono , Spain.

Abstract

A new and highly fluorescent family of unsymmetrical organoboron complexes containing 5-(pyridin-2-ylmethylene)imidazolidine-2,4-dione moieties has been synthesized in three steps. These compounds show strong absorptions covering a wide range of the UV-vis spectrum and are strongly emissive (varphif of up to 0.92 in CH3CN). Moreover, two fluorophores that include an alkyne or an azide group at the end of the alkyl chain and with potential utility in bioorthogonal chemistry have been developed. One of these, in which the glycol substituent provides an enhanced water solubility without compromising the fluorescence (varphif = 0.85 in water), may be of particular importance.