Publications

Trifluorinated Pyrimidine-Based A2B Antagonists: Optimization and Evidence of Stereospecific Recognition

Ana Mallo-Abreu, María Majellaro, Willem Jespers, Jhonny Azuaje, Olga Caamaño, XerardoGarcía-Mera, José M.Brea, MaríaI.Loza, HugoGutieŕrez-de-Terań,
and Eddy Sotelo

J. Med. Chem. 2019, 62, 9315−9330

https://pubs.acs.org/doi/10.1021/acs.jmedchem.9b01340

Free-Energy Calculations for Bioisosteric Modifications of A3 Adenosine Receptor Antagonists

Zuzana Jandova, Willem Jespers, Eddy Sotelo, Hugo Gutiérrez-de-Terán and Chris Oostenbrink

Int. J. Mol. Sci. 2019, 20(14), 3499 https://www.mdpi.com/1422-0067/20/14/3499

Clinical validation of blood/brain glutamate grabbing in acute ischemic stroke.

Silva, A., Pérez-Díaz, A., Santamaría, M., Correa-Paz, C., Rodríguez-Yáñez, M., Ardá, A., Pérez-Mato, M., Iglesias-Rey, R., Brea, J., Azuaje, J., Sotelo, E., Sobrino, T., Loza, M., Castillo, J., Campos, F

Annals of Neurology, 2018, 84, 260-273. https://doi.org/10.1002/ana.25286

Structural Mapping ogf Adenosine Receptor Mutations: Ligand Binding and Signaling Mechanisms.

Jespers, W., Schiedel, A. C., Heitman, L., Cooke, R., Leene, L., van Westen, G. J., Glorian, D. E., Muller, C. E., Sotelo, E., Gutiérrez de Terán, H.

Trends in Pharmacological Sciences, 2018, 39, 75-89. https://doi.org/10.1016/j.tips.2017.11.001

Three-Dimensional Printing in Catalysis: Combining 3D Heterogeneous Copper and Palladium Catalysts for Multicatalytic Multicomponent Reactions

Díaz-Marta, A.S. Tubío, C.R., Carbajales, C., Fernandez, C., Escalante, L., Sotelo, E., Guitián, F., Barrio, V. L., Gil, A., Coelho, A.

ACS Catalysis. 2018, 8, 392-404 https://pubs.acs.org/doi/abs/10.1021/acscatal.7b02592

Development of Fluorescent Probes that Target Serotonin 5HT2B receptors

Azuaje, J., López, Paula, Iglesias, A., De la Fuente, R., Pérez-Rubio, J. M., García, D., Pérez, D., Stepniewski, T., García-Mera, X., Loza, M. I., Cadavid, M. I. Brea, J., Sotelo, E.*

Scientific Reports. 2017, 7, 11370-3. https://www.nature.com/articles/s41598-017-11370-2

Effect of Nitrogen Atom Substitution in A3 Adenosine Receptor Binding: N(4,6-Dirarylpyridin-2-yl)acetamides as Potent and Selective Antagonists

Azuaje, J., Jespers, W., Yaziji, V., Mallo, A., Majellaro, M., Caamaño, O., Loza, M. I., Cadavid, M. I. Brea, J. Gutiérrez de Terán, H., Sotelo, E.*

Journal of Medicinal Chemistry, 2017, 60, 7502-7511. https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.7b00860

3-Oxopyridazin-5-yl-Chalcone Hybrids: Potent Antiplatelet Agents that Prevent GP IIb/IIIa Activation

El Maatougui, A., Yañez, M., Crespo, A., Fraiz, N., Coelho, A., Raviña, E., Cano, E., Loza, M. I., Brea, J., Gutiérrez de Terán, H., Sotelo, E.*

ChemistrySelect, 2017, 2, 4920-4933. https://onlinelibrary.wiley.com/doi/10.1002/slct.201700243

Synthesis and Characterization of a New Bivalent Ligand Combining Caffeine and Docosahexaenoic Acid

Fernandez-Dueñas, V., Morato, X., Ciruela, F., Azuaje, J., Sotelo, E.* Cordobilla, B., Domingo, J.C.

Molecules. 2017, 22, 3661-11. https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6155394/

Enantiospecific Recognition at the A2B Adenosine Receptor by Alkyl 2-Cyanoimino-4-substituted-6-methyl-1,2,3,4-tetrahydropyrimiidine-5-carboxylates

Carbajales, C., Azuaje, J., Oliveira, A., Loza, M.I., Brea, J., Cadavid, M.I., Masaguer, C. F., García-Mera, X., Gutiérrez de Terán, H., Sotelo, E.*

Journal of Medicinal Chemistry. 2017, 60, 3372-3382. https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.7b00138

An Efficient and Recyclable 3D Printed α-Al2O3 Catalyst for the Multicomponent Assembly of Bioactive Heterocycles

Azuaje, J., Tubio, C.R., Escalante, L., Gomez, M., Coelho, A., Caamaño, O., Gil, A., Sotelo, E.*

Applied Catalysis, A: General, 2017, 530, 203-210. https://www.sciencedirect.com/science/article/pii/S0926860X16305701

Multicomponent Assembly of the Kinesin Spindle Protein Inhibitor CPUYJ039 and Analogues as Antimitotic Agents.

Carbajales, C., Sawada, J-C., Marzano, G., Sotelo, E., Escalante, L., Sanchez-Diaz Marta, A., García-Mera, X., Asai, A., Coelho, A.

ACS Comb. Sci. 2017, 19, 153-160. https://pubs.acs.org/doi/abs/10.1021/acscombsci.6b00166

Structure-Based Rational Design of Adenosine Receptor Ligands.

Gutiérrez-de-Terán, H. Sallander, J. Sotelo, E.

Current Topics In Medicinal Chemistry, 2017, 17, 40-58. https://www.ingentaconnect.com/contentone/ben/ctmc/2017/00000017/00000001/art00007

Drug Structural Features Affect Drug Delivery from Hyperbranched Polyesteramide Hot Melt Extrudates.

Raviña-Eirín, E., Azuaje, J., Sotelo, E. Gómez-Amoza, J. L., Martínez-Pacheco, R.

European Journal of Pharmaceutics and Biopharmaceutics, 2016, 102, 1-78. https://www.sciencedirect.com/science/article/pii/S0939641116300108

Discovery of Potent and Highly Selective Adenosine A2B Receptor Antagonists Chemotypes.

El Maatougi, A., Azuaje, J., González-Gómez, M., Míguez, G., Crespo, A., García-Mera, X.,  Gutiérrez de Terán, H., Sotelo, E.*

Journal of Medicinal Chemistry, 2016, 59, 1967-1983. https://pubs.acs.org/doi/abs/10.1021/acs.jmedchem.5b01586

3D-Printing of a Heterogeneous Copper-Based Catalyst

Tubio, C. R., Azuaje, J., Escalante, L., Coelho, A., Sotelo, E. Gil, A.

Journal of Catalysis, 2016, 334, 110-115. https://www.sciencedirect.com/science/article/pii/S0021951715003838

Pyrazin-2(1H)-ones as a Novel Class of Selective A3 Adenosine Receptor Antagonists.

Azuaje, J., Carbajales, C, González-Gomes, M., Coelho, A., Caamaño, O., Gutierrez de Terán, H., Sotelo, E.

Future Medicinal Chemistry, 2015, 7, 1373-1380. https://www.future-science.com/doi/10.4155/fmc.15.69

Sol-Gel Entrapped Cu in Silica Matrix: An Efficienct Heterogeneous Nanocatalyst For Huisgen, and Ullmann Reactions.

Diz, P., Gil, A., Guitían, F., El Maatougui, A., Azuaje, J., Pernas, P., Sotelo, E., Coelho, A.

Applied Catalysis A: General  , 2015, 502, 86-95. https://www.sciencedirect.com/science/article/pii/S0926860X1530003X

Integrated Ugi-Based Assembly of Functional, Skeletal and Stereochemically Diverse 1,4-Benzodiazepin-2-ones.

Azuaje, J., Pérez-Rubio, J. M., Yaziji, V., El Maatougui, González-Gómez, J. C., Masaguer, C. F., Sánchez-Pedregal, V., Navarro-Vázquez, A., Teijeira, M., Sotelo, E.*

J. Org. Chem. 2015, 80, 1533-1549. https://pubs.acs.org/doi/abs/10.1021/jo502382q

Computer-Aided Design of GPCR Ligands.

Gutiérrez-de-Terán, H., Keranen, H., Azuaje, J., Rodriguez, D., Sotelo, E.

Methods in Molecular Biology, 2015, 1272, 1272-1291. https://link.springer.com/protocol/10.1007%2F978-1-4939-2336-6_19

Structure-Based Design of Novel KSP-Eg5 Inhibitors Assisted by a Targeted Multicomponent Reaction.

Carbajales, C., Prado, M. A., Gutiérrez-de-Terán, H., Cores, A., Azuaje, J., Novio, S., Nuñez, M. J., Fernández, B., Sotelo, E., García-Mera, X., Sánchez-Lazo, P., Freire-Garabal, M., Coelho, A.

ChemBioChem, 2014, 15, 1471-1480. https://onlinelibrary.wiley.com/doi/full/10.1002/cbic.201402089

Ugi-Based Approaches to Quinoxaline Libraries.

Azuaje, J., El Maatougui, García-Mera, X., Sotelo, E.*

ACS Combinatorial Science, 2014, 16, 403-411. https://pubs.acs.org/doi/abs/10.1021/co500036n

Discovery of 3,4-Dihydropyrimidin-2(1H)-ones as a Novel Class of Potent and Selective A2B Adenosine Receptor Antagonists.

Crespo, A., El Maatougui, A.,Biagini, P., Azuaje, J., Coelho, A., García-Mera, X., Brea, J., Loza, M. I., Cadavid, M. I., Sotelo, E.*

ACS Medicinal Chemistry Letters, 2013, 4, 1031-1036. https://pubs.acs.org/doi/10.1021/ml400185v

Copper-Catalyzed Huisgen 1,3-Dipolar Cycloaddition Under Oxidative Conditions: Polymer-Assisted Assembly of 4-Acyl-1-Substituted-1,2,3-Triazoles

Diz, P., Coelho, A., El Maatougui, A., Azuaje, J., Caamaño, O., Gil, A., Sotelo, E.*

The Journal of Organic Chemistry, 2013, 78, 6540-6549. https://pubs.acs.org/doi/10.1021/jo400800j

Three-Component Assembly of Structurally Diverse 2-Aminopyrimidine-5-carbonitriles.

Val, C., Crespo, A., El Maatougui, A., Azuaje, J. A., Coelho, A., Sotelo, E.*

ACS Comb. Sci., 2013, 15, 370-378. https://pubs.acs.org/doi/abs/10.1021/co4000503

Multicomponent Assembly of Diverse Pyrazin-2(1H)-one Chemotypes

Azuaje, J., El Maatougui, A., Pérez-Rubio, J. M., Coelho, A., Fernández, F. Sotelo, E.*

The Journal of Organic Chemistry, 2013, 78, 4402-4409. https://pubs.acs.org/doi/abs/10.1021/jo4003163

Selective and potent Adenosine A3 Receptor Antagonists by Methoxyaryl Substitution on the N-(2,6-Diarylpyrimidin-4-yl)acetamide scaffold.

Yaziji, V., Rodríguez, D., Gutiérrez de Terán, H., Coelho, A., El Maatougui, A., Brea, J., Loza, M. I., Garcia-Mera, X., Cadavid, M.I., Sotelo, E.*

European Journal of Medicinal Chemistry. 2013, 59, 235-242. https://www.sciencedirect.com/science/article/pii/S0223523412006794

Discovery and Preliminary SAR of 5-Arylidene-2,2,-dimethyl-1,3-dioxane-2,4-diones as Platelet Aggregation Inhibitors.

El Maatougui, A., Azuaje, J., Coelho, A., Cano, E., Yañez, M., Yaziji, V., Carbajales, C., Sotelo, E.*

Combinatorial Chemistry & High Throughput Screening, 2012, 15, 551-554. http://www.eurekaselect.com/100357

Pyrimidine Derivatives as Potent and Selective A3 Adenosine Receptor Antagonists.

. Yaziji, V., Rodríguez, D., Gutiérrez de Terán, H., Coelho, A., Brea, J., Loza, M. I., Garcia-Mera, X., Cadavid, M.I., Caamaño, Sotelo, E.*

Journal of Medicinal Chemistry. 2011, 54, 457-471. https://pubs.acs.org/doi/abs/10.1021/jm100843z

Supported Tosic Acid as Highly Robust and Eco-Friendly Isocyanide´s Scavengers.

Azuaje, J., Al Maatougui, A., Blanco, J.M., Coelho, A., Sotelo, E.*

ACS Combinatorial Science, 2011, 13, 89-95. https://pubs.acs.org/doi/10.1021/co100035z

Silica-Supported Aluminum Chloride-Assisted Solution Phase Synthesis of Pyridazinone-Based Antiplatelet Agents.

El Maatougui, A., Azuaje, J., Sotelo, E., Caamaño, O., Coelho, A.

ACS Combinatorial Science 2011, 13, 7-12. https://pubs.acs.org/doi/abs/10.1021/co100017h

Convergent Assembly of Structurally Diverse Quinazolines.

Crespo, A., Coelho, A., Diz, P., Fernández, F., Novoa de Armas, H., Sotelo, E.*

Organic & Biomolecular Chemistry, 2011, 9, 351-357. https://pubs.acs.org/doi/abs/10.1021/co100017h

Polymer Supported 1,5,7-triazabicylo[4,4,0]dec-5-ene as Polyvalent Ligands in the Copper Catalysed Huisgen 1,3-Dipolar Cycloaddition.

Coelho, A., Díz, P., Caamaño, O., Sotelo, E.*

Advanced Synthesis & Catalysis, 2010, 352, 1179-1192. https://onlinelibrary.wiley.com/doi/10.1002/adsc.200900680

Divergent Solution Phase Synthesis of Diarylpirimidines as Selective A3 Adenosine Receptor Antagonsits

Yaziji, V., Coelho, A., El Maatougui, Brea, J., Loza, M. I., Garcia-Mera, X., Sotelo, E.*

Journal of Combinatorial Chemistry, 2009, 11, 519-522. https://pubs.acs.org/doi/10.1021/cc900044k

Synthetic Applications of Polystyrene 1,1,3,3-Tetramethylguanidine

Coelho, A., Crespo, A., Fernández, F., Biagini, P., Stefanachi, A., Sotelo, E.*

Combinatorial Chemistry & Highthroughput Screening, 2008, 11, 843-847. http://www.eurekaselect.com/68075

Click Chemistry Approach to Assembly Proline Mimetic Libraries Containing 1,4-Substituted 1,2,3-Triazoles.

Rodriguez-Borges, J. E., Gonçalves, S., do Vale, M. L., García-Mera, X., Coelho, A., Sotelo, E.

Journal of Combinatorial Chemistry, 2008, 10, 372-375. https://pubs.acs.org/doi/10.1021/cc800035z

Design, Synthesis and Biological Evaluation of Glycine-Based Molecular Tongs as Inhibitors of α-β 1-40 Aggregation in Vitro.

Cellamare, S., Stefanachi, A., Antonella, S., Basile, T., Catto, M., Campagna, F., Sotelo, E., Carotti, A.

Bioorganic & Medicinal Chemistry, 2008, 16, 4810-4822. https://www.sciencedirect.com/science/article/pii/S096808960800271X

1,3- and 8-Substituted-9-Deazaxanthines as Potent and Selective Antagonists at the Human A2B Adenosine Receptor

Stefanachi, A., Brea, J. M., Cadavid M. I., Centeno, N. B., Esteve, C., Loza, M. I., Martínez, A., Nieto, R., Raviña, E., Sanz, F., Segarra, V., Sotelo, E., Vidal, B., Carotti, A.

Bioorganic & Medicinal Chemistry, 2008, 16, 2852-2859. https://www.sciencedirect.com/science/article/pii/S0968089608000035

2-Substituted 4-, 5- and 6-[(1E)-3-oxo-3-phenylprop-1-en-1-yl]pyridazin-3(2H)-ones and 2-Substituted 4,5-bis[(1E)-3-oxo-3-phenylprop-1-en-1-yl]pyridazin-3(2H)-ones as Potent Platelet Aggregation Inhibitors: Design, Synthesis and SAR Studies.

Meyers, C., Yáñez, M., Elmatougi, A., Verhest, T., Coelho, A., Fraiz, N., Lemière, G. L. F., García-Mera, X., Laguna, R., Cano, E., Maes, B. U. W., Sotelo, E.*

Bioorganic & Medicinal Chemistry Lett. 2008, 18, 793-797. https://www.sciencedirect.com/science/article/pii/S0960894X07013431

Synthesis, Adenosine Receptor Binding and 3D-QSAR- of 4-Substituted 2-(2´-furyl)-1,2,4-triazolo[1,5-a]quinoxalines.

Martínez A., Gutierrez de Terán, H., Brea, J. M., Raviña, E., Loza, M. I., Cadavid, M. I., Sanz, F., Segarra, V., Vidal, B. Sotelo, E.*

Bioorganic & Medicinal Chemistry, 2008, 16, 2103-2113. https://www.sciencedirect.com/science/article/pii/S0968089608000515

Design, Synthesis and Structure Activity Relationships of a Novel Series of 5-Alkylidenenpyridazin-3-ones with a non c-AMP-Based Antiplatelet Activity.

Coelho, A., Raviña, E., Yáñez, M., Fraiz, N., Laguna, R., Cano, E., Sotelo, E.*

Journal of Medicinal Chemistry, 2007, 50, 6476-6484. https://pubs.acs.org/doi/10.1021/jm061401d

Parallel Regulation By Olanzapine Of The Patterns Of Expression Of 5-Ht2a And D3 Receptors In Rat Central Nervous System And Blood Cells.

Padín; J. F., Rodríguez; M.A., Domínguez; E., Dopeso-Reyes; I. G., Buceta; M., Cano; E., Sotelo, E., Caruncho; H. J., Cadavid; M. I., Castro; M., Loza, M.I.

Neuropharmacology, 2006, 51, 923-932. https://www.sciencedirect.com/science/article/pii/S0028390806001882

Expanding the Chemical Diversity of Azinone Libraries by A Consecutive Alkylation/Palladium-Catalysed Functionalization Strategy

Coelho, A., Sotelo, E.*

Journal of Combinatorial Chemistry, 2005, 7, 526-529. https://pubs.acs.org/doi/10.1021/cc050036t

Reactivity of 5-Alkynylpyridazinones Toward Hydrochloric Acid

Coelho, A., Novoa, H., Peeters, O.M., Blaton, N., Sotelo, E.*

Tetrahedron, 2005, 61, 4785-4791. https://www.sciencedirect.com/science/article/pii/S004040200500428X

Reactivity of 5-Iodopyridazin-3(2H)-ones in Palladium-Catalysed Reactions

Coelho, A., Sotelo, E., Novoa, H., Peeters, O.M., Blaton, N., Raviña, E.

Tetrahedron, 2004, 60, 12177-12189. https://www.sciencedirect.com/science/article/pii/S0040402004016941

8-Substituted-9-deazaxanthines as Adenosine Receptor Ligands: Design, Synthesis and Structure-affinity Relationships at A2B

Carotti, A., Stefanachi, A., Raviña, E., Sotelo, E., Loza, M. I., Cadavid, M. I., Centeno, N. B.

European Journal of Medicinal Chemistry, 2004, 39, 879-887. https://www.sciencedirect.com/science/article/pii/S0223523404001618

Efficient Heck Alkenylation at position 5 of the 6-phenyl-3(2H)-pyridazinone System.

Coelho, A., Sotelo, E., Novoa, H., Blaton, N., Peeters, O.M., Raviña, E.

Tetrahedron Letters, 2004, 45, 3459-3463. https://www.sciencedirect.com/science/article/pii/S004040390400509X

Facile Solution Phase Combinatorial Synthesis of Highly Substituted Pyridazinones

Sotelo, E.*

Molecular Diversity 2004, 8, 159-163. https://link.springer.com/article/10.1023/B%3AMODI.0000025628.01102.81

Stille-Based Approaches in the Synthesis of 6-phenyl-5-Substituted-3(2H)-pyridazinones.

Sotelo, E., Coelho, A., Raviña, E.

Chem. Pharm. Bull., 2003, 5, 427-430. https://www.jstage.jst.go.jp/article/cpb/51/4/51_4_427/_pdf

Sonogashira Approaches in The Synthesis of 5-Substituted-6-phenyl-3(2H)-pyridazinones.

Coelho, A., Sotelo, E., Raviña, E.

Tetrahedron, 2003, 59, 2477-2484. https://www.sciencedirect.com/science/article/pii/S0040402003002631

Retro-Ene-Assisted Palladium-Catalysed Synthesis of 4,5-Disubstituted-3(2H)-pyridazinones.

Sotelo, E., Coelho, A., Raviña, E.

Tetrahedron Lett., 2003, 44, 4459-4462. https://www.sciencedirect.com/science/article/pii/S0040403903010293

Traceless Solid Phase Synthesis of 4,5- and 5,6-Diaryl-3(2H)-pyridazinones.

Sotelo, E., Raviña, E.

Synlett, 2003, 1113-1116. https://www.thieme-connect.com/products/ejournals/pdf/10.1055/s-2003-39882.pdf