Category Archives: Noticias

J. Environ. Chem. Eng. 02.22

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, in press, Open access
DOI: 10.1016/j.jece.2022.107486

The efficient metal-free electrosynthesis of 2,4-dinitrophenyl iodide is here reported starting from 2,4-dinitrophenylhydrazine. Surprisingly this dinitrated arylhydrazine minimizes, under the applied experimental conditions, any anodic multilayered film formation. This sustainable iodide-mediated oxidative dehydrazination enables coupling reaction of electrogenerated iodine with aryl radicals from electron-deficient arylhydrazines employing electricity as the driving force and an inexpensive halogen source. A mechanistic proposal explaining the formation of aryl iodides is presented and discussed.

XVII SIJ-RSEQ organisation

XVII SIJ-RSEQ organisation

Several members of the group have been in charge of organising the 17th RSEQ Young Researchers Symposium, held in Alcalá de Henares from 23 to 26 November.

XVII Simposio de Investigadores Jóvenes de la RSEQ

The group has also made several contributions:

– Oral:
· Synthesis of seven- and eight-membered rings by Brønsted acid-catalyzed cyclization of biphenyl embedded trienynes
Jaime Tostado Sánchez, Juan J. Vaquero, Manuel A. Fernández-Rodríguez

– Flash:
· Enantio- and diastereoselective cyclopropanation of trans-alkenylboronates: Synthesis of versatile (trifluoromethyl)cyclopropylboronates
Julia Altarejos, David Sucunza, Juan José Vaquero, Javier Carreras

– Poster:
· Synthesis of a series of novel bicyclic amino acids
Álvaro González, Francisco José Torrero, José Luis Aceña, Juan José Vaquero

· Metal-free straightforward synthesis of boron-functionalized indenes and fulvenes by borylative cyclization
Ester Sans Panadés, Patricia García-García, Juan J. Vaquero, Cintia Virumbrales, Roberto Sanz, Manuel A. Fernández-Rodríguez

· SYNTHESIS OF PEPTIDE NUCLEIC ACIDS (PNAs) FOR THE TREATMENT OF CHRONIC KIDNEY DISEASE
Francisco Maqueda Zelaya, Verónica Miguel, José Luis Aceña, Santiago Lamas, Juan José Vaquero

· Synthesis of 4-membered rings fused lactams by gold(I) catalyzed
cyclization of alkynylcyclobutanamides

Guillermo G. Otárola, María Soledad Garre, Estíbaliz Merino, David Sucunza, Juan J. Vaquero, Patricia García-García

· Regioselective Ir-Catalyzed C−H Borylation of 4a,8a-Dihydro-4a-Aza-8a-Boranaphthalene
Isabel Valencia, Patricia García, David Sucunza, Juan J. Vaquero

· DEVELOPMENT OF A SYNTHETIC ROUTE TO LAETEVIRENOL A
Lucía Sánchez-Jiménez, Ana Milián, Jaime Tostado, Juan J. Vaquero, Patricia García-García, Manuel A. Fernández-Rodríguez

· Kinetic resolution in transannular Morita-Baylis-Hillman reaction:
approach to the synthesis of guaiane-type sesquiterpenes

Rubén Manzano, Raquel Mato, Efraím Reyes, Liher Prieto, Uxue Uria, Luisa Carrillo, Jose L. Vicario

· Electrochemical synthesis of aryl iodides from arylhydrazines
Clara Mañas Hernández, Guillermo Otárola, Estíbaliz Merino, Noemi Salardón, Belén Batanero

J. Org. Chem. 11.21

1,10a-Dihydro-1-aza-10a-boraphenanthrene and 6a,7-Dihydro-7-aza-6a-boratetraphene: Two New Fluorescent BN-PAHs

Isabel Valencia, Patricia García-García, David Sucunza*, Francisco Mendicuti, Juan J. Vaquero*

J. Org. Chem. 2021, 86, 23, 16259–16267
DOI: 10.1021/acs.joc.1c01095

Previously unknown 1,10a-dihydro-1-aza-10a-boraphenanthrene and 6a,7-dihydro-7-aza-6a-boratetraphene have been efficiently synthesized. Bromination of these BN-PAHs proceeds with complete regioselectivity, resulting in the formation of different substituted derivatives via cross-coupling reactions. These compounds exhibit rather high fluorescence quantum yields (up to ϕF = 0.80).

Eur. J. Med. Chem. 10.21

Pyridazino-pyrrolo-quinoxalinium salts as highly potent and selective leishmanicidal agents targeting trypanothione reductase

Héctor de Lucio, Javier García-Marín, Patricia Sánchez-Alonso, Juan Carlos García-Soriano, Miguel Ángel Toro, Juan J Vaquero, Federico Gago, Ramón Alajarín, Antonio Jiménez-Ruiz

Eur. J. Med. Chem. , 2021
DOI: 10.1016/j.ejmech.2021.113915

Fifteen pyridazino-pyrrolo-quinoxalinium salts were synthesized and tested for their antiprotozoal activity against Leishmania infantum amastigotes. Eleven of them turned out to be leishmanicidal, with EC(50) values in the nanomolar range, and displayed low toxicity against the human THP-1 cell line. Selectivity indices for these compounds range from 10 to more than 1000. Compounds 3b and 3f behave as potent inhibitors of the oxidoreductase activity of the essential enzyme trypanothione disulfide reductase (TryR). Interestingly, binding of 3f is not affected by high trypanothione concentrations, as revealed by the noncompetitive pattern of inhibition observed when tested in the presence of increasing concentrations of this substrate. Furthermore, when analyzed at varying NADPH concentrations, the characteristic pattern of hyperbolic uncompetitive inhibition supports the view that binding of NADPH to TryR is a prerequisite for inhibitor-protein association. Similar to other TryR uncompetitive inhibitors for NADPH, 3f is responsible for TryR-dependent reduction of cytochrome c in a reaction that is typically inhibited by superoxide dismutase.