Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity

Autores
Acosta, Paola; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; Sortino, Maximiliano Andrés; Zacchino, Susana Alicia Stella; Quiroga, Jairo
Año de publicación
2016
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
Novel fused pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidines 5 were prepared by a solvent-free microwave assisted reaction of heterocyclic o-aminonitriles 3 and cyanopyridines 4 in the presence of tBuOK as catalyst. This protocol provides a versatile procedure for the synthesis of the title compounds with the advantages of easy work-up, mild reaction conditions and good yields. All compounds were also tested for antifungal properties against two clinically important fungi; Candida albicans and Cryptococcus neoformans. Several compounds showed moderate activity against both fungi, being 5a the most active compound. Analysis of the antifungal behavior of properly grouped compounds allowed to determine that the position of the N in the pyrimidyl moiety per se does not play a role in the activity. In turn, the type of 4-R substituent appears to influence the activity. In addition to the above considerations, the lipophilicity of compounds measured as log. P showed to be not related to the activity and regarding the dipole moment (D), no net correlation was observed, although it is the most active compounds (% inhibition >50%) that have a D ≥ 7.5, mainly against C. albicans.
Fil: Acosta, Paola. Universidad del Valle; Colombia
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Ortiz, Alejandro. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario; Argentina
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Materia
ANTIFUNGAL ACTIVITY
CYANOPYRIDINES
MICROWAVE IRRADIATION
O-AMINONITRILES
PYRAZOLOPYRIDOPYRIMIDINES
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/180024
Acceder
id CONICETDig_c275ef55b32806a2ca4c64fd5610274b
oai_identifier_str oai:ri.conicet.gov.ar:11336/180024
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activityAcosta, PaolaInsuasty, BraulioOrtiz, AlejandroAbonia, RodrigoSortino, Maximiliano AndrésZacchino, Susana Alicia StellaQuiroga, JairoANTIFUNGAL ACTIVITYCYANOPYRIDINESMICROWAVE IRRADIATIONO-AMINONITRILESPYRAZOLOPYRIDOPYRIMIDINEShttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1Novel fused pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidines 5 were prepared by a solvent-free microwave assisted reaction of heterocyclic o-aminonitriles 3 and cyanopyridines 4 in the presence of tBuOK as catalyst. This protocol provides a versatile procedure for the synthesis of the title compounds with the advantages of easy work-up, mild reaction conditions and good yields. All compounds were also tested for antifungal properties against two clinically important fungi; Candida albicans and Cryptococcus neoformans. Several compounds showed moderate activity against both fungi, being 5a the most active compound. Analysis of the antifungal behavior of properly grouped compounds allowed to determine that the position of the N in the pyrimidyl moiety per se does not play a role in the activity. In turn, the type of 4-R substituent appears to influence the activity. In addition to the above considerations, the lipophilicity of compounds measured as log. P showed to be not related to the activity and regarding the dipole moment (D), no net correlation was observed, although it is the most active compounds (% inhibition >50%) that have a D ≥ 7.5, mainly against C. albicans.Fil: Acosta, Paola. Universidad del Valle; ColombiaFil: Insuasty, Braulio. Universidad del Valle; ColombiaFil: Ortiz, Alejandro. Universidad del Valle; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario; ArgentinaFil: Quiroga, Jairo. Universidad del Valle; ColombiaElsevier2016-01info: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/11336/180024Acosta, Paola; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; Sortino, Maximiliano Andrés; et al.; Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity; Elsevier; Arabian Journal of Chemistry; 9; 3; 1-2016; 481-4921878-5352CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S1878535215000714info:eu-repo/semantics/altIdentifier/doi/10.1016/j.arabjc.2015.03.002info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-nd/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-29T10:45:00Zoai:ri.conicet.gov.ar:11336/180024instacron: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 10:45:01.038CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
title Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
spellingShingle Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
Acosta, Paola
ANTIFUNGAL ACTIVITY
CYANOPYRIDINES
MICROWAVE IRRADIATION
O-AMINONITRILES
PYRAZOLOPYRIDOPYRIMIDINES
title_short Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
title_full Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
title_fullStr Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
title_full_unstemmed Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
title_sort Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity
dc.creator.none.fl_str_mv Acosta, Paola
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Quiroga, Jairo
author Acosta, Paola
author_facet Acosta, Paola
Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Quiroga, Jairo
author_role author
author2 Insuasty, Braulio
Ortiz, Alejandro
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Quiroga, Jairo
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv ANTIFUNGAL ACTIVITY
CYANOPYRIDINES
MICROWAVE IRRADIATION
O-AMINONITRILES
PYRAZOLOPYRIDOPYRIMIDINES
topic ANTIFUNGAL ACTIVITY
CYANOPYRIDINES
MICROWAVE IRRADIATION
O-AMINONITRILES
PYRAZOLOPYRIDOPYRIMIDINES
purl_subject.fl_str_mv https://purl.org/becyt/ford/1.4
https://purl.org/becyt/ford/1
dc.description.none.fl_txt_mv Novel fused pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidines 5 were prepared by a solvent-free microwave assisted reaction of heterocyclic o-aminonitriles 3 and cyanopyridines 4 in the presence of tBuOK as catalyst. This protocol provides a versatile procedure for the synthesis of the title compounds with the advantages of easy work-up, mild reaction conditions and good yields. All compounds were also tested for antifungal properties against two clinically important fungi; Candida albicans and Cryptococcus neoformans. Several compounds showed moderate activity against both fungi, being 5a the most active compound. Analysis of the antifungal behavior of properly grouped compounds allowed to determine that the position of the N in the pyrimidyl moiety per se does not play a role in the activity. In turn, the type of 4-R substituent appears to influence the activity. In addition to the above considerations, the lipophilicity of compounds measured as log. P showed to be not related to the activity and regarding the dipole moment (D), no net correlation was observed, although it is the most active compounds (% inhibition >50%) that have a D ≥ 7.5, mainly against C. albicans.
Fil: Acosta, Paola. Universidad del Valle; Colombia
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Fil: Ortiz, Alejandro. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario; Argentina
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
description Novel fused pyrazolo[4',3':5,6]pyrido[2,3-d]pyrimidines 5 were prepared by a solvent-free microwave assisted reaction of heterocyclic o-aminonitriles 3 and cyanopyridines 4 in the presence of tBuOK as catalyst. This protocol provides a versatile procedure for the synthesis of the title compounds with the advantages of easy work-up, mild reaction conditions and good yields. All compounds were also tested for antifungal properties against two clinically important fungi; Candida albicans and Cryptococcus neoformans. Several compounds showed moderate activity against both fungi, being 5a the most active compound. Analysis of the antifungal behavior of properly grouped compounds allowed to determine that the position of the N in the pyrimidyl moiety per se does not play a role in the activity. In turn, the type of 4-R substituent appears to influence the activity. In addition to the above considerations, the lipophilicity of compounds measured as log. P showed to be not related to the activity and regarding the dipole moment (D), no net correlation was observed, although it is the most active compounds (% inhibition >50%) that have a D ≥ 7.5, mainly against C. albicans.
publishDate 2016
dc.date.none.fl_str_mv 2016-01
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/11336/180024
Acosta, Paola; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; Sortino, Maximiliano Andrés; et al.; Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity; Elsevier; Arabian Journal of Chemistry; 9; 3; 1-2016; 481-492
1878-5352
CONICET Digital
CONICET
url http://hdl.handle.net/11336/180024
identifier_str_mv Acosta, Paola; Insuasty, Braulio; Ortiz, Alejandro; Abonia, Rodrigo; Sortino, Maximiliano Andrés; et al.; Solvent-free microwave-assisted synthesis of novel pyrazolo [4′, 3′: 5, 6] pyrido [2, 3-d] pyrimidines with potential antifungal activity; Elsevier; Arabian Journal of Chemistry; 9; 3; 1-2016; 481-492
1878-5352
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.sciencedirect.com/science/article/pii/S1878535215000714
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.arabjc.2015.03.002
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-nd/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
application/pdf
dc.publisher.none.fl_str_mv Elsevier
publisher.none.fl_str_mv Elsevier
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_ 1844614489035505664
score 13.070432

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