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Noticias

6th Symposium of Medicinal Chemistry Young Researchers

6th Symposium of Medicinal Chemistry Young Researchers


SYNTHESIS OF MODULATORS OF INTEGRIN-LINKED KINASE (ILK)
S. Simón de la Fuente, F. Maqueda, J. García-Marín, J.L. Aceña and J.J. Vaquero

SYNTHESIS OF SMALL MOLECULES AS MIMETICS OF THE EPITOPE SEGMENT IN ILK-α-PARVIN PROTEIN-PROTEIN INTERACTION
M. Ramírez Rozalén, J. García Marín, R. Alajarín and J. J. Vaquero

NEW SYNTHETIC STRATEGIES FOR TREATMENT OF THE RENAL DISEASE: SYNTHESIS OF PEPTIDE NUCLEIC ACIDS
F. Maqueda-Zelaya, V. Miguel, J. L. Aceña, S. Lamas and J. J. Vaquero

NOVEL HIGHLY FLUORESCENT FAMILY OF UNSYMMETRIC ORGANOBORON COMPLEXES WITH 5-(PYRIDIN-2-YLMETHYLENE)IMIDAZOLIDINE-2,4-DIONE SYSTEMS
M. S. Garre, R. Losantos, S. Gutiérrez, D. Sucunza, P. García-García, D. Sampedro and J. J. Vaquero

SYNTHESIS OF NOVEL β-TURN LIKE MIMETICS
A. González, N. Mateu, J. L. Aceña, S. Fustero and J. J. Vaquero

 

Noticias

XXXVII Bienal RSEQ conference

XXXVII Bienal RSEQ conference

Flash communications:

– Gold (I)-Catalyzed Cycloisomerization of 1,3,5-Trien-7-ynes: A Novel and General Approach to Phenanthrenes
Manuel A. Fernández-Rodríguez, Patricia García-García, Roberto Sanz, Juan J. Vaquero, Ana Milián-López

– Electrophilic Cyclizations of Alkynylcyclobutanes and -cyclopropanes
Patricia García-García, David Sucunza, Enrique Aguilar, Juan J. Vaquero, M. Soledad Garre

Poster:

– Azaborine synthesis by cascade borocyclization of o-alkynyl anilines
Ester Sans-Panadés, Manuel A. Fernández-Rodríguez, Patricia García-García, Juan J. Vaquero

2019, AzaBN, Publicación

Abengozar et al. J Org Chem. 2019;84(11):7113-7122. A New Member of the BN-Phenanthrene Family: Understanding the Role of the B-N Bond Position.

Publications > Abengozar et al

J Org Chem. 2019, 84, 7113

A New Member of the BN-Phenanthrene Family: Understanding the Role of the B-N Bond Position.

Alberto Abengozar1, David Sucunza1, Patricia Garcia-Garcia1, Diego Sampedro2, Adrian Perez-Redondo1, Juan J Vaquero1

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

3,4-Dihydro-4-aza-3-boraphenanthrene, which shows the highest fluorescence quantum yield of all nonsubstituted BN-phenanthrenes reported to date (varphiF = 0.61), has been synthesized in only three steps (76% overall yield) from easily accessible 1-bromo-2-vinylnaphthalene, along with several substituted derivatives. The reactivity of these previously unknown BN-aromatic compounds toward organolithium compounds and bromine has been studied. This latter reaction affords bromo-substituted compounds that are suitable for further functionalization via Suzuki and Sonogashira couplings, with complete regioselectivity. The optical properties and excited state deactivation mechanisms of selected compounds were studied using computational methods.

2019, AzaBN, Publicación

Abengozar et al. Beilstein J Org Chem. 2019;15:1257-1261. Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene.

Publications > Abengozar et al

Beilstein J. Org. Chem. 2019, 15, 1257 PubMed 31293672

Remarkable effect of alkynyl substituents on the fluorescence properties of a BN-phenanthrene.

Alberto Abengozar, David Sucunza, Patricia Garcia-Garcia, Juan J Vaquero

Departamento de Quimica Organica y Quimica Inorganica, Instituto de Investigacion Quimica "Andres M. del Rio" (IQAR), Universidad de Alcala, 28871-Alcala de Henares, Madrid, Spain.

Keywords: BN-phenanthrene; alkyne; cross-coupling; fluorescence; heterocycles

Abstract

A series of BN-phenanthrenes with substituents of a diverse nature have been synthesized by palladium-catalyzed cross-coupling reactions of a common chloro-substituted precursor, which was made from readily available materials in only four steps. Evaluation of the photophysical properties of the prepared compounds unveiled an impressive effect of the presence of alkynyl substituents on the fluorescence quantum yield, which improved from 0.01 in the parent compound to up to 0.65 in derivatives containing a triple bond.

Noticias

J. Org. Chem. 05.2019

A New Member of the BN-Phenanthrene Family: Understanding the Role of the B—N Bond Position

Alberto Abengózar, David Sucunza, Patricia García-García, Diego Sampedro, Adrián Pérez-Redondo, and Juan J. Vaquero

J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.9b00800

3,4-Dihydro-4-aza-3-boraphenanthrene, which shows the highest fluorescence quantum yield of all nonsubstituted BN-phenanthrenes reported to date (ϕF = 0.61), has been synthesized in only three steps (76% overall yield) from easily accessible 1-bromo-2-vinylnaphthalene, along with several substituted derivatives. The reactivity of these previously unknown BN-aromatic compounds toward organolithium compounds and bromine has been studied. This latter reaction affords bromo-substituted compounds that are suitable for further functionalization via Suzuki and Sonogashira couplings, with complete regioselectivity. The optical properties and excited state deactivation mechanisms of selected compounds were studied using computational methods.

Miembros

Estibaliz Merino

Estibaliz Merino Marcos

Associate Professor

    • 2019-present: Senior Research Fellow , Talent Attraction Program of Community of Madrid-Type 1, Universidad de Alcalá (Madrid)
    • 2013-2019: Associated Researcher, University of Zurich (Switzerland) (Prof. Cristina Nevado). Development of new methodologies in organic synthesis and study of reaction mechanisms through computational calculations.
    • 2011-2013: «JAE-Doc» Researcher, Instituto de Química Orgánica General (IQOG-CSIC) (Madrid) (Prof. Félix Sánchez). Design and synthesis of new functionalized micro and mesoporous organic materials.
    • 2010-2011: «Juan de la Cierva» Researcher, Instituto de Tecnología Química (ITQ, CSIC-UPV) (Prof. Avelino Corma). Development and study of the properties of new multifunctional hybrid materials.
    • 2007-2009: Postdoctoral Researcher, RWTH Aachen University (Germany) (Prof. Magnus Rueping).
    • 2007: Ph.D. Universidad Autónoma de Madrid (Prof. Mª Carmen Carreño) Nuevas Aplicaciones de los Sulfóxidos: Síntesis de Moléculas Naturales a partir de p-(tolilsulfinilmetil)-p-Quinoles. Síntesis y Propiedades Fotocrómicas de Sulfinil Azocompuestos Enantiopuros.
    • 2000: Graduated at the Universidad Autónoma de Madrid.
2019, Publicación, Renal

Valino-Rivas et al. Trends Mol Med. 2019;25(4):341-360. NIK as a Druggable Mediator of Tissue Injury.

Publications > Valino-Rivas et al

Trends Mol Med. 2019, 25, 341 PubMed 30926358

NIK as a Druggable Mediator of Tissue Injury.

Lara Valino-Rivas1, Juan Jose Vaquero2, David Sucunza2, Sara Gutierrez2, Ana B Sanz1, Manuel Fresno3, Alberto Ortiz1, 4, a, Maria Dolores Sanchez-Nino1, 4, a

1. Department of Nephrology and Hypertension, Instituto de Investigacion Sanitaria (IIS) Fundacion Jimenez Diaz, School of Medicine, Universidad Autonoma de Madrid (UAM), Red de Investigacion Renal (REDINREN), and Fundacion Renal Inigo Alvarez de Toledo (FRIAT), Madrid, Spain.  2. Departamento de Quimica Organica y Quimica Inorganica, Universidad de Alcala and REDINREN, Madrid, Spain.  3. Centro de Biologia Molecular Severo Ochoa, Consejo Superior de Investigaciones Cientificas de la UAM, Madrid, Spain.  4. These authors contributed equally. Electronic address:.

a. aortiz@fjd.es  a. mdsanchez@fjd.es

Keywords: *MAP3K14; *NIK; *TWEAK; *acute kidney injury; *apoptosis; *autoimmunity; *cell death; *chronic kidney disease; *cirrhosis; *diabetes; *epigenetic; *esteatohepatitis; *hepatitis; *inflammation; *mantle lymphoma; *myeloid leukemia; *osteoporosis; *sarcopenia; *verteporfin

Abstract

NF-kappaB-inducing kinase (NIK, MAP3K14) is best known as the apical kinase that triggers non-canonical NF-kappaB activation and by its role in the immune system. Recent data indicate a role for NIK expressed by non-lymphoid cells in cancer, kidney disease, liver injury, glucose homeostasis, osteosarcopenia, vascular calcification, hematopoiesis, and endothelial function. The spectrum of NIK-associated disease now ranges from immunodeficiency (when NIK is defective) to autoimmunity, cancer, sterile inflammation, fibrosis, and metabolic disease when NIK is overactive. The development of novel small-molecule NIK inhibitors has paved the way to test NIK targeting to treat disease in vivo, and may eventually lead to NIK targeting in the clinic. In addition, NIK activators are being explored for specific conditions such as myeloid leukemia.

2019, AzaBN, Publicación

Abengozar et al. Org Lett. 2019;21(8):2550-2554. Synthesis, Functionalization, and Optical Properties of 1,2-Dihydro-1-aza-2-boraphenanthrene and Several Highly Fluorescent Derivatives.

Publications > Abengozar et al

Org Lett. 2019, 21, 2550 PubMed 30951317

Synthesis, Functionalization, and Optical Properties of 1,2-Dihydro-1-aza-2-boraphenanthrene and Several Highly Fluorescent Derivatives.

Alberto Abengozar1, Patricia Garcia-Garcia1, David Sucunza1, Diego Sampedro2, Adrian Perez-Redondo1, Juan J Vaquero1

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

Previously unknown 1,2-dihydro-1-aza-2-boraphenanthrene has been synthesized in only three steps from 2-bromo-1-vinylnaphthalene. The reactivity of this new BN-phenanthrene, and of several substituted derivatives, has been tested against bromine and organolithium compounds. Bromination proceeded with complete regioselectivity, affording bromo-substituted compounds suitable for further functionalization via cross-coupling reactions. This new family of BN-phenanthrenes exhibits a substantial increase in the quantum yield (up to varphiF = 0.93) with respect to phenanthrene.

2019, Au, Publicación

Garre et al. J Org Chem. 2019;:. Regiodivergent Electrophilic Cyclizations of Alkynylcyclobutanes for the Synthesis of Cyclobutane-Fused O-Heterocycles.

Publications > Garre et al

J. Org. Chem. 2019, 84, 9, 5712 PubMed 30896164

Regiodivergent Electrophilic Cyclizations of Alkynylcyclobutanes for the Synthesis of Cyclobutane-Fused O-Heterocycles.

M Soledad Garre1, David Sucunza1, Enrique Aguilar2, Patricia Garcia-Garcia1, Juan J Vaquero1

1. Departamento de Quimica Organica y Quimica Inorganica, Campus Cientifico-Tecnologico, Facultad de Farmacia , Universidad de Alcala (IRYCIS) , Autovia A-II, Km 33.1 , 28805 Alcala de Henares , Madrid , Spain.  2. Departamento de Quimica Organica e Inorganica, Instituto Universitario de Quimica Organometalica "Enrique Moles" , Universidad de Oviedo , C/Julian Claveria, 8 , 33006 Oviedo , Spain.

Abstract

Cyclobutane-fused dihydropyrans and methylenetetrahydrofurans are highly interesting cores found in numerous natural products. Both these cores are selectively prepared from a common alkynylcyclobutane precursor bearing an appended hydroxyl group herein. Thus, cyclobutane-fused dihydropyrans can be obtained by a selective 6-endo-dig iodocyclization, whereas gold-catalyzed 5-exo-dig cycloisomerization provides a bicyclic core containing a methylenetetrahydrofuran moiety as major product. Several cyclobutane-fused O-heterocycles with diverse substituents are synthesized following the reported methodology.