Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity

Autores
Acosta, Paola; Butassi, Estefanía; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; Zacchino, Susana Alicia Stella; Quiroga, Jairo
Año de publicación
2015
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.
Fil: Acosta, Paola. Universidad del Valle; Colombia
Fil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Ortiz, Alejandro. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Materia
ANTIFUNGAL ACTIVITY
ANTITUMORAL ACTIVITY
CANDIDA ALBICANS
CRYPTOCOCCUS NEOFORMANS
MICROWAVE IRRADIATION
PYRAZOLONAPHTHYRIDINES
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:11336/180266
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/180266
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activityAcosta, PaolaButassi, EstefaníaInsuasty, BraulioOrtiz, AlejandroAbonia, RodrigoZacchino, Susana Alicia StellaQuiroga, JairoANTIFUNGAL ACTIVITYANTITUMORAL ACTIVITYCANDIDA ALBICANSCRYPTOCOCCUS NEOFORMANSMICROWAVE IRRADIATIONPYRAZOLONAPHTHYRIDINEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.Fil: Acosta, Paola. Universidad del Valle; ColombiaFil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Insuasty, Braulio. Universidad del Valle; ColombiaFil: Ortiz, Alejandro. Universidad del Valle; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Quiroga, Jairo. Universidad del Valle; ColombiaMolecular Diversity Preservation International2015-05info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/180266Acosta, Paola; Butassi, Estefanía; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; et al.; Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity; Molecular Diversity Preservation International; Molecules; 20; 5; 5-2015; 8499-85201420-3049CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.3390/molecules20058499info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/20/5/8499info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T09:33:21Zoai:ri.conicet.gov.ar:11336/180266instacron: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:34982025-09-29 09:33:21.932CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
spellingShingle Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
Acosta, Paola
ANTIFUNGAL ACTIVITY
ANTITUMORAL ACTIVITY
CANDIDA ALBICANS
CRYPTOCOCCUS NEOFORMANS
MICROWAVE IRRADIATION
PYRAZOLONAPHTHYRIDINES
title_short Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_full Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_fullStr Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_full_unstemmed Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
title_sort Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity
dc.creator.none.fl_str_mv Acosta, Paola
Butassi, Estefanía
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Zacchino, Susana Alicia Stella
Quiroga, Jairo
author Acosta, Paola
author_facet Acosta, Paola
Butassi, Estefanía
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Zacchino, Susana Alicia Stella
Quiroga, Jairo
author_role author
author2 Butassi, Estefanía
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Zacchino, Susana Alicia Stella
Quiroga, Jairo
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIFUNGAL ACTIVITY
ANTITUMORAL ACTIVITY
CANDIDA ALBICANS
CRYPTOCOCCUS NEOFORMANS
MICROWAVE IRRADIATION
PYRAZOLONAPHTHYRIDINES
topic ANTIFUNGAL ACTIVITY
ANTITUMORAL ACTIVITY
CANDIDA ALBICANS
CRYPTOCOCCUS NEOFORMANS
MICROWAVE IRRADIATION
PYRAZOLONAPHTHYRIDINES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.
Fil: Acosta, Paola. Universidad del Valle; Colombia
Fil: Butassi, Estefanía. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Ortiz, Alejandro. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
description The microwave assisted reaction between heterocyclic o-aminonitriles 1 and cyclic ketones 2 catalyzed by zinc chloride led to new series of pyrazolo[3,4-b] [1,8]naphthyridin-5-amines 3 in good yields. This procedure provides several advantages such as being environmentally friendly, high yields, simple work-up procedure, broad scope of applicability and the protocol provides an alternative for the synthesis of pyrazolonaphthyridines. The whole series showed antifungal activities against Candida albicans and Cryptococcus neoformans standardized strains, being compounds with a 4-p-tolyl substituent of the naphthyridin scheleton (3a, 3d and 3g), the most active ones mainly against C. albicans, which appear to be related to their comparative hydrophobicity. Among them, 3d, containing a cyclohexyl fused ring, showed the best activity. The anti-Candida activity was corroborated by testing the three most active compounds against clinical isolates of albicans and non-albicans Candida strains. These compounds were also screened by the US National Cancer Institute (NCI) for their ability to inhibit 60 different human tumor cell lines. Compounds 3a and 3e showed remarkable antitumor activity against cancer cell lines, with the most important GI50 values ranging from 0.62 to 2.18 μM.
publishDate 2015
dc.date.none.fl_str_mv 2015-05
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/11336/180266
Acosta, Paola; Butassi, Estefanía; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; et al.; Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity; Molecular Diversity Preservation International; Molecules; 20; 5; 5-2015; 8499-8520
1420-3049
CONICET Digital
CONICET
url http://hdl.handle.net/11336/180266
identifier_str_mv Acosta, Paola; Butassi, Estefanía; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; et al.; Microwave-assisted synthesis of novel pyrazolo[3,4-g][1,8]naphthyridin-5-amine with potential antifungal and antitumor activity; Molecular Diversity Preservation International; Molecules; 20; 5; 5-2015; 8499-8520
1420-3049
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.3390/molecules20058499
info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1420-3049/20/5/8499
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
application/pdf
dc.publisher.none.fl_str_mv Molecular Diversity Preservation International
publisher.none.fl_str_mv Molecular Diversity Preservation International
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
_version_ 1844613024159105024
score 13.070432

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