Master’s Thesis “Drug Discovery” 2019

School of Drug Discovery of the Interuniversity Master’s Degree in Drug Discovery

In this edition, five works tutored in the group have been presented. Congratulations!

• Julia Altarejos “Síntesis estereoselectiva de trifluorometilciclopropilboronatos”
• Paula Flores “Síntesis de compuestos policíclicos mediante ciclaciones electrofílicas de eninos”
• Miriam Ramírez “Synthesis of small molecules as mimetics of the epitope segment in ILK-a-parvin protein-protein interaction”
• Alexey Sanduev “Design and synthesis of dicationic cromophores with application in bioimaging”
• Silvia Simón “Synthesis of modulators of integrin-linked kinase (ILK)”

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

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

Dr. Aleksey Vasilev talk

Dr. Aleksey Aleksandrov Vasilev, Sofia University (Bulgaria)
E-Z Photoisomerization Stimulated by Triplet-Triplet Annihilation Photon Energy Up-conversion Light 
Multipurpose Building, UAH. June 27th, 12.00.

Vasilev talk

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.

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

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

Org. Lett., Article ASAP
DOI: 10.1021/acs.orglett.9b00448

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 ϕ_F = 0.93) with respect to phenanthrene.

Regiodivergent electrophilic cyclizations of alkynylcyclobutanes for the synthesis of cyclobutane-fused O-heterocycles

María Soledad Garre, David Sucunza, Enrique Aguilar, Patricia García-García, and Juan J. Vaquero

J. Org. Chem., Article ASAP
DOI: 10.1021/acs.joc.9b00618

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 the bicyclic core containing a methylenetetrahydrofuran moiety as major product. Several cyclobutane-fused O-heterocycles with diverse substitution are synthesized following the reported methodology.

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