Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions

Autores
Londoño Salazar, Jennifer; Restrepo Acevedo, Andrés; Torres, John Eduard; Abonia, Rodrigo; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Le Lagadec, Ronan; Cuenú Cabezas, Fernando
Año de publicación
2024
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
In 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.
Fil: Londoño Salazar, Jennifer. Universidad del Quindio; Colombia
Fil: Restrepo Acevedo, Andrés. Universidad del Quindio; Colombia
Fil: Torres, John Eduard. Universidad del Quindio; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Le Lagadec, Ronan. Universidad Nacional Autónoma de México; México
Fil: Cuenú Cabezas, Fernando. Universidad del Quindio; Colombia
Materia
MIZOROKI-HECK REACTION
PALLADIUM
ANTIFUNGAL ACTIVITY
PYRAZOLE
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/239144
Acceder
id CONICETDig_65340a4637813e0915e3da0f813f963d
oai_identifier_str oai:ri.conicet.gov.ar:11336/239144
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck ReactionsLondoño Salazar, JenniferRestrepo Acevedo, AndrésTorres, John EduardAbonia, RodrigoSvetaz, Laura AndreaZacchino, Susana Alicia StellaLe Lagadec, RonanCuenú Cabezas, FernandoMIZOROKI-HECK REACTIONPALLADIUMANTIFUNGAL ACTIVITYPYRAZOLEhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1In 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.Fil: Londoño Salazar, Jennifer. Universidad del Quindio; ColombiaFil: Restrepo Acevedo, Andrés. Universidad del Quindio; ColombiaFil: Torres, John Eduard. Universidad del Quindio; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Le Lagadec, Ronan. Universidad Nacional Autónoma de México; MéxicoFil: Cuenú Cabezas, Fernando. Universidad del Quindio; ColombiaMDPI2024-06info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/239144Londoño Salazar, Jennifer; Restrepo Acevedo, Andrés; Torres, John Eduard; Abonia, Rodrigo; Svetaz, Laura Andrea; et al.; Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions; MDPI; Catalysts; 14; 6; 6-2024; 1-292073-4344CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4344/14/6/387info:eu-repo/semantics/altIdentifier/doi/10.3390/catal14060387info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-22T11:03:56Zoai:ri.conicet.gov.ar:11336/239144instacron:CONICETInstitucionalhttp://ri.conicet.gov.ar/Organismo científico-tecnológicoNo correspondehttp://ri.conicet.gov.ar/oai/requestdasensio@conicet.gov.ar; lcarlino@conicet.gov.arArgentinaNo correspondeNo correspondeNo correspondeopendoar:34982025-10-22 11:03:56.809CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
title Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
spellingShingle Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
Londoño Salazar, Jennifer
MIZOROKI-HECK REACTION
PALLADIUM
ANTIFUNGAL ACTIVITY
PYRAZOLE
title_short Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
title_full Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
title_fullStr Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
title_full_unstemmed Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
title_sort Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions
dc.creator.none.fl_str_mv Londoño Salazar, Jennifer
Restrepo Acevedo, Andrés
Torres, John Eduard
Abonia, Rodrigo
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Le Lagadec, Ronan
Cuenú Cabezas, Fernando
author Londoño Salazar, Jennifer
author_facet Londoño Salazar, Jennifer
Restrepo Acevedo, Andrés
Torres, John Eduard
Abonia, Rodrigo
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Le Lagadec, Ronan
Cuenú Cabezas, Fernando
author_role author
author2 Restrepo Acevedo, Andrés
Torres, John Eduard
Abonia, Rodrigo
Svetaz, Laura Andrea
Zacchino, Susana Alicia Stella
Le Lagadec, Ronan
Cuenú Cabezas, Fernando
author2_role author
author
author
author
author
author
author
dc.subject.none.fl_str_mv MIZOROKI-HECK REACTION
PALLADIUM
ANTIFUNGAL ACTIVITY
PYRAZOLE
topic MIZOROKI-HECK REACTION
PALLADIUM
ANTIFUNGAL ACTIVITY
PYRAZOLE
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv In 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.
Fil: Londoño Salazar, Jennifer. Universidad del Quindio; Colombia
Fil: Restrepo Acevedo, Andrés. Universidad del Quindio; Colombia
Fil: Torres, John Eduard. Universidad del Quindio; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Svetaz, Laura Andrea. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Le Lagadec, Ronan. Universidad Nacional Autónoma de México; México
Fil: Cuenú Cabezas, Fernando. Universidad del Quindio; Colombia
description In 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.
publishDate 2024
dc.date.none.fl_str_mv 2024-06
dc.type.none.fl_str_mv info:eu-repo/semantics/article
info:eu-repo/semantics/publishedVersion
http://purl.org/coar/resource_type/c_6501
info:ar-repo/semantics/articulo
format article
status_str publishedVersion
dc.identifier.none.fl_str_mv http://hdl.handle.net/11336/239144
Londoño Salazar, Jennifer; Restrepo Acevedo, Andrés; Torres, John Eduard; Abonia, Rodrigo; Svetaz, Laura Andrea; et al.; Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions; MDPI; Catalysts; 14; 6; 6-2024; 1-29
2073-4344
CONICET Digital
CONICET
url http://hdl.handle.net/11336/239144
identifier_str_mv Londoño Salazar, Jennifer; Restrepo Acevedo, Andrés; Torres, John Eduard; Abonia, Rodrigo; Svetaz, Laura Andrea; et al.; Synthesis and Characterization of New Bases Derived from Nitrophenylpyrazoles, Coordination to Palladium and Antifungal Activity and Catalytic Activity in Mizoroki–Heck Reactions; MDPI; Catalysts; 14; 6; 6-2024; 1-29
2073-4344
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/2073-4344/14/6/387
info:eu-repo/semantics/altIdentifier/doi/10.3390/catal14060387
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv MDPI
publisher.none.fl_str_mv MDPI
dc.source.none.fl_str_mv reponame:CONICET Digital (CONICET)
instname:Consejo Nacional de Investigaciones Científicas y Técnicas
reponame_str CONICET Digital (CONICET)
collection CONICET Digital (CONICET)
instname_str Consejo Nacional de Investigaciones Científicas y Técnicas
repository.name.fl_str_mv CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas
repository.mail.fl_str_mv dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar
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score 12.982451

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