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dc.contributorVall d'Hebron Barcelona Hospital Campus
dc.contributor.authorMasip, Victor
dc.contributor.authorLirio, Ángel
dc.contributor.authorLópez-Huertas, Albert
dc.contributor.authorCuenca, Ana Belen
dc.contributor.authorPuig de la Bellacasa, Raimon
dc.contributor.authorAbrisqueta Costa, Pablo
dc.date.accessioned2022-06-20T07:33:59Z
dc.date.available2022-06-20T07:33:59Z
dc.date.issued2021-12-15
dc.identifier.citationMasip V, Lirio A, Sánchez-López A, Cuenca AB, Puig de la Bellacasa R, Abrisqueta P, et al. Expanding the Diversity at the C-4 Position of Pyrido[2,3-d]pyrimidin-7(8H)-ones to Achieve Biological Activity against ZAP-70. Pharmaceuticals. 2021 Dec 15;14(12):1311.
dc.identifier.issn1424-8247
dc.identifier.urihttp://hdl.handle.net/11351/7712
dc.descriptionCross-coupling; Tyrosine kinase inhibitors
dc.description.abstractPyrido[2,3-d]pyrimidin-7(8H)-ones have attracted widespread interest due to their similarity with nitrogenous bases found in DNA and RNA and their potential applicability as tyrosine kinase inhibitors. Such structures, presenting up to five diversity centers, have allowed the synthesis of a wide range of differently substituted compounds; however, the diversity at the C4 position has mostly been limited to a few substituents. In this paper, a general synthetic methodology for the synthesis of 4-substituted-2-(phenylamino)-5,6-dihydropyrido[2,3-d]pyrimidin-7(8H)-ones is described. By using cross-coupling reactions, such as Ullmann, Buchwald–Hartwig, Suzuki–Miyaura, or Sonogashira reactions, catalyzed by Cu or Pd, we were able to describe new potential biologically active compounds. The resulting pyrido[2,3-d]pyrimidin-7(8H)-ones include N-alkyl, N-aryl, O-aryl, S-aryl, aryl, and arylethynyl substituents at C4, which have never been explored in connection with the biological activity of such heterocycles as tyrosine kinase inhibitors, in particular as ZAP-70 inhibitors.
dc.language.isoeng
dc.publisherMDPI
dc.relation.ispartofseriesPharmaceuticals;14(12)
dc.rightsAttribution 4.0 International
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.sourceScientia
dc.subjectQuímica farmacèutica
dc.subjectEstructura molecular
dc.subjectPirimidines
dc.subject.meshPyrimidinones
dc.subject.mesh/chemical synthesis
dc.subject.meshMolecular Structure
dc.subject.meshChemistry, Pharmaceutical
dc.titleExpanding the Diversity at the C-4 Position of Pyrido[2,3-d]pyrimidin-7(8H)-ones to Achieve Biological Activity against ZAP-70
dc.typeinfo:eu-repo/semantics/article
dc.identifier.doi10.3390/ph14121311
dc.subject.decspirimidinonas
dc.subject.decs/síntesis química
dc.subject.decsestructura molecular
dc.subject.decsquímica farmacéutica
dc.relation.publishversionhttps://doi.org/10.3390/ph14121311
dc.type.versioninfo:eu-repo/semantics/publishedVersion
dc.audienceProfessionals
dc.contributor.organismesInstitut Català de la Salut
dc.contributor.authoraffiliation[Masip V, Lirio A, Sánchez-López A, Cuenca AB, Puig de la Bellacasa R] Grup de Química Farmacèutica, IQS School of Engineering, Universitat Ramon Llull, Barcelona, Spain. [Abrisqueta P] Servei d’Hematologia, Vall d’Hebron Hospital Universitari, Barcelona, Spain. Experimental Hematology Group, Vall d’Hebron Institute of Oncology (VHIO), Barcelona, Spain
dc.identifier.pmid34959711
dc.identifier.wos000748871700001
dc.relation.projectidinfo:eu-repo/grantAgreement/ES/PE2013-2016/PI18%2F01392
dc.rights.accessrightsinfo:eu-repo/semantics/openAccess


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