Synthesis and characterization of new bases derived from nitrophenylpyrazoles, coordination to palladium and antifungal activity and catalytic activity in Mizoroki–Heck reactions

Vista sencilla de ítem
dc.citation.titleCatalysts
dc.citation.volume14
dc.contributor.orcidhttps://orcid.org/0000-0002-4974-3599
dc.contributor.orcidhttps://orcid.org/0000-0003-3256-0961
dc.contributor.orcidhttps://orcid.org/0000-0002-5679-2081
dc.contributor.orcidhttps://orcid.org/0000-0003-2997-6720
dc.creatorLondoño Salazar, Jennifer
dc.creatorRestrepo Acevedo, Andrés
dc.creatorTorres, John Eduard
dc.creatorAbonia, Rodrigo
dc.creatorSvetaz, Laura Andrea
dc.creatorZacchino, Susana A.
dc.creatorLe Lagadec, Ronan
dc.creatorCuenú Cabezas, Fernando
dc.date.accessioned2025-03-12T13:10:27Z
dc.date.available2025-03-12T13:10:27Z
dc.date.issued2024-06-16
dc.description.abstractIn this study, we report the synthesis of eight Schiff bases (3–10) type N-heterocycle (N-het) using conventional refluxing conditions as well as different eco-friendly techniques such as grinding, thermal fusion, microwave irradiation (MWI) and ultrasound, all of them in the presence of a catalytic amount of acetic acid. These procedures had the additional advantage of being environmentally friendly and high-yield, making these protocols an alternative for Schiff-base syntheses. The obtained Schiff bases were coordinated to palladium, generating new complexes of type [Pd2Cl4(N-het)2]. Complexes [Pd2Cl4(5)2] and [Pd2Cl4(9)2] showed high activity and selectivity for a model Mizoroki–Heck C-C coupling reaction of styrene with iodobenzene and bromobenzaldehydes. All compounds and complexes were evaluated for antifungal activity against clinically important fungi such as Candida albicans and Cryptococcus neoformans. Although the Schiff bases (3–10) showed low antifungal activity against both fungi, some of their palladium complexes such as [Pd2Cl4(3)2], [Pd2Cl4(5)2], [Pd2Cl4(8)2] and [Pd2Cl4(10)2] showed comparatively higher antifungal effects mainly against C. neoformans. The product of the Mizoroki–Heck-type C-C coupling reactions, 4-styrylbenzaldehyde, was isolated and purified to be later used in the synthesis of four new nitrophenylpyrazole derivatives of styrylimine, which also displayed antifungal activity, especially against C. neoformans.
dc.description.filFil: Londoño Salazar, Jennifer. University of Oklahoma. Department of Chemistry and Biochemistry. Price Family Institute of Structural Biology; United States.
dc.description.filFil: Londoño Salazar, Jennifer. Universidad del Quindío. Facultad de Ciencias Básicas y Tecnologías. Laboratorio en Química Inorgánica y Catálisis; Colombia.
dc.description.filFil: Restrepo Acevedo, Andrés. Universidad del Quindío. Facultad de Ciencias Básicas y Tecnologías. Laboratorio en Química Inorgánica y Catálisis; Colombia.
dc.description.filFil: Restrepo Acevedo, Andrés. Universidad Nacional Autónoma de México. Instituto de Química; México.
dc.description.filFil: Torres, John Eduard. Universidad del Quindío. Facultad de Ciencias Básicas y Tecnologías. Laboratorio en Química Inorgánica y Catálisis; Colombia.
dc.description.filFil: Torres, John Eduard. Universidad Nacional Autónoma de México. Instituto de Química; México.
dc.description.filFil: Abonia, Rodrigo. Universidad del Valle. Facultad de Ciencias Naturales y Exactas. Departamento de Química; Colombia.
dc.description.filFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.
dc.description.filFil: Zacchino, Susana A. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Argentina.
dc.description.filFil: Le Lagadec, Ronan. Universidad Nacional Autónoma de México. Instituto de Química; México.
dc.description.filFil: Cuenú Cabezas, Fernando. Universidad del Quindío. Facultad de Ciencias Básicas y Tecnologías. Laboratorio en Química Inorgánica y Catálisis; Colombia.
dc.description.sponsorshipUniversidad del Quindío (Uniquindío): project 1050
dc.description.sponsorshipUniversidad del Valle (Colombia)
dc.description.sponsorshipUniversidad Nacional Autónoma de México. Dirección General de Asuntos del Personal Académico (UNAM-DGAPA): PAPIIT project IN-211522
dc.description.sponsorshipAgencia Nacional de Promoción de la Investigación, el Desarrollo Tecnológico y la Innovación (Agencia I+D+i): PICT2014-1170
dc.description.sponsorshipConsejo Nacional de Investigaciones Científicas y Técnicas (CONICET)
dc.description.sponsorshipUniversidad Nacional de Rosario (UNR)
dc.description.versionpeerreviewed
dc.format.extent1-29
dc.identifier.e-issn2073-4344
dc.identifier.urihttps://hdl.handle.net/2133/29050
dc.language.isoen
dc.publisherMDPI
dc.relation.publisherversionhttps://doi.org/10.3390/catal14060387
dc.relation.publisherversionhttps://www.mdpi.com/2073-4344/14/6/387
dc.rightsopenAccess
dc.rights.holderLondoño Salazar, Jennifer
dc.rights.holderRestrepo Acevedo, Andrés
dc.rights.holderTorres, John Eduard
dc.rights.holderAbonia, Rodrigo
dc.rights.holderSvetaz, Laura Andrea
dc.rights.holderZacchino, Susana A.
dc.rights.holderLe Lagadec, Ronan
dc.rights.holderCuenú Cabezas, Fernando
dc.rights.holderUniversidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas
dc.rights.textAttribution 4.0 Internationalen
dc.rights.urihttp://creativecommons.org/licenses/by/4.0/
dc.subjectMizoroki–Heck reaction
dc.subjectPalladium
dc.subjectAntifungal activity
dc.subjectPyrazole
dc.subjectCatalytic activity
dc.subjectSchiff bases
dc.subjectCryptococcus neoformans
dc.subjectCandida albicans
dc.titleSynthesis and characterization of new bases derived from nitrophenylpyrazoles, coordination to palladium and antifungal activity and catalytic activity in Mizoroki–Heck reactions
dc.typearticulo
dc.type.collectionarticulo
dc.type.versionpublishedVersion

Archivos

Bloque original
Mostrando 1 - 1 de 1
Miniatura
Nombre:
File - catalysts-14-00387.pdf
Tamaño:
4.01 MB
Formato:
Adobe Portable Document Format
Descargar
Bloque de licencias
Mostrando 1 - 1 de 1
Nombre:
license.txt
Tamaño:
3.87 KB
Formato:
Item-specific license agreed upon to submission
Descripción:
Descargar

Colecciones

(FBIOyF) Departamento de Química Orgánica - Artículos