Category Archives: Noticias

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.
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.
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.
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).

Noticias

J. Org. Chem. 12.2019

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 Garre, Raúl Losantos, Sara Gutiérrez, David Sucunza, Patricia García-García, Diego Sampedro and Juan J. Vaquero

J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.9b02451

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 (ϕf 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 (ϕf = 0.85 in water), may be of particular importance.

Noticias

UK-Spain Organometallic Chemistry Symposium

UK-Spain Organometallic Chemistry Symposium (USOCS2019)

 

UK-Spain Organometallic Chemistry Symposium (USOCS2019),  Alcalá de Henares, September 17-19th:

· BN-Arenes: Synthesis, Reactivity and Properties
Alberto Abéngozar, Isabel Valencia, Miguel Ángel Fernández, Luis Manuel Frutos, Antonio Salgado, Adrián Pérez Redondo, Patricia García-García, David Sucunza, Juan J. Vaquero

· Decarbonylation Processes in k3 -(N^C^C) Gold (III) Carboxylates
Estíbaliz Merino, Hélène Beucher, Alexandre Genoux, Thomas Fox, Cristina Nevado

· Gold-catalyzed regiodivergent cyclization of alkynylcyclobutanes
M. Soledad Garre, David Sucunza, Estíbaliz Merino, Enrique Agular, Patricia García-García, Juan J. Vaquero

· Stereoselective synthesis of versatile trifluoromethyl substituted borocyclopropanes
Julia Altarejos, David Sucunza, Ana Caballero, Pedro J. Pérez, Juan J. Vaquero, Javier Carreras

Noticias

International Symposium on Advances in Synthetic and Medicinal Chemistry

EFMC-ASMC19 (International Symposium on Advances in Synthetic and Medicinal Chemistry) and ASMC-YSMC (6th EFMC Young Medicinal Chemist Symposium)

 

INTO THE ILK-αPARVIN INTERACTION AS A NEW STRATEGY AGAINST CHRONIC KIDNEY DISEASE
García Marín, Javier; De Frutos, Sergio; Griera, Mercedes; Alajarín Ferrandez, Ramón; Griera Merino, Mercedes; Vaquero López, Juan J.; Rodriguez Puyol, Diego; Rodriguez Puyol, Manuel

· International Symposium on Advances in Synthetic and Medicinal Chemistry, September 1-5th, Athens
· 6th EFMC Young Medicinal Chemist Symposium, September 5-6th, Athens