Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combina...

Autores
Ramirez, Juan; Rodriguez, Maria Victoria; Quiroga, Jairo; Abonia, Rodrigo; Sortino, Maximiliano Andrés; Zacchino, Susana Alicia Stella; Insuasty, Braulio
Año de publicación
2014
Idioma
inglés
Tipo de recurso
artículo
Estado
versión publicada
Descripción
The a,b-unsaturated carbonyl compounds 5a–f were prepared by reaction between 2-chloro-4- morpholinothiazol-5-carbaldehyde 3 and substituted acetophenones 4a–f. Treatment of compounds 5a–f with hydrazine hydrate employing mild reaction conditions led to the formation of 4,5-dihydro- 1H-pyrazoles 6a–f. Then the treatment with acetic anhydride or formic acid afforded the expected 4,5- dihydro-1H-pyrazoles 7a–f and 8a–f. The antifungal activity of each series of synthesized compounds was determined against the clinically important fungi Candida albicans and Cryptococcus neoformans. In addition, the most active compounds 7e and 7f were tested in combination with the commercial antifungal agents: fluconazole, itraconazole, and amphotericin B. Compound 7e showed a synergistic effect with fluconazole against C. albicans while 7f showed synergistic activities with all tested antifungal drugs against the same yeast
Fil: Ramirez, Juan. Universidad del Valle; Colombia
Fil: Rodriguez, Maria Victoria. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
Materia
Antifungal Activity
2-Chloro-4-Morpholinothiazol-5-Carbaldehyde
Commercial Antifungal Agents
4,5- Dihydro-1h-Pyrazoles
Synergistic Effect
Nivel de accesibilidad
acceso abierto
Condiciones de uso
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
Repositorio
CONICET Digital (CONICET)
Institución
Consejo Nacional de Investigaciones Científicas y Técnicas
OAI Identificador
oai:ri.conicet.gov.ar:11336/29968
Acceder
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oai_identifier_str oai:ri.conicet.gov.ar:11336/29968
network_acronym_str CONICETDig
repository_id_str 3498
network_name_str CONICET Digital (CONICET)
spelling Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.Ramirez, JuanRodriguez, Maria VictoriaQuiroga, JairoAbonia, RodrigoSortino, Maximiliano AndrésZacchino, Susana Alicia StellaInsuasty, BraulioAntifungal Activity2-Chloro-4-Morpholinothiazol-5-CarbaldehydeCommercial Antifungal Agents4,5- Dihydro-1h-PyrazolesSynergistic Effecthttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1The a,b-unsaturated carbonyl compounds 5a–f were prepared by reaction between 2-chloro-4- morpholinothiazol-5-carbaldehyde 3 and substituted acetophenones 4a–f. Treatment of compounds 5a–f with hydrazine hydrate employing mild reaction conditions led to the formation of 4,5-dihydro- 1H-pyrazoles 6a–f. Then the treatment with acetic anhydride or formic acid afforded the expected 4,5- dihydro-1H-pyrazoles 7a–f and 8a–f. The antifungal activity of each series of synthesized compounds was determined against the clinically important fungi Candida albicans and Cryptococcus neoformans. In addition, the most active compounds 7e and 7f were tested in combination with the commercial antifungal agents: fluconazole, itraconazole, and amphotericin B. Compound 7e showed a synergistic effect with fluconazole against C. albicans while 7f showed synergistic activities with all tested antifungal drugs against the same yeastFil: Ramirez, Juan. Universidad del Valle; ColombiaFil: Rodriguez, Maria Victoria. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; ArgentinaFil: Quiroga, Jairo. Universidad del Valle; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; ArgentinaFil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; ArgentinaFil: Insuasty, Braulio. Universidad del Valle; ColombiaWiley VCH Verlag2014-04info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/29968Ramirez, Juan; Rodriguez, Maria Victoria; Quiroga, Jairo; Abonia, Rodrigo; Sortino, Maximiliano Andrés; et al.; Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.; Wiley VCH Verlag; Archiv Der Pharmazie; 347; 8; 4-2014; 566-5750365-6233CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1002/ardp.201400084info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ardp.201400084/abstractinfo:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-10-15T14:30:14Zoai:ri.conicet.gov.ar:11336/29968instacron: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:34982025-10-15 14:30:15.128CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse
dc.title.none.fl_str_mv Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
title Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
spellingShingle Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
Ramirez, Juan
Antifungal Activity
2-Chloro-4-Morpholinothiazol-5-Carbaldehyde
Commercial Antifungal Agents
4,5- Dihydro-1h-Pyrazoles
Synergistic Effect
title_short Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
title_full Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
title_fullStr Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
title_full_unstemmed Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
title_sort Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.
dc.creator.none.fl_str_mv Ramirez, Juan
Rodriguez, Maria Victoria
Quiroga, Jairo
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Insuasty, Braulio
author Ramirez, Juan
author_facet Ramirez, Juan
Rodriguez, Maria Victoria
Quiroga, Jairo
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Insuasty, Braulio
author_role author
author2 Rodriguez, Maria Victoria
Quiroga, Jairo
Abonia, Rodrigo
Sortino, Maximiliano Andrés
Zacchino, Susana Alicia Stella
Insuasty, Braulio
author2_role author
author
author
author
author
author
dc.subject.none.fl_str_mv Antifungal Activity
2-Chloro-4-Morpholinothiazol-5-Carbaldehyde
Commercial Antifungal Agents
4,5- Dihydro-1h-Pyrazoles
Synergistic Effect
topic Antifungal Activity
2-Chloro-4-Morpholinothiazol-5-Carbaldehyde
Commercial Antifungal Agents
4,5- Dihydro-1h-Pyrazoles
Synergistic Effect
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 a,b-unsaturated carbonyl compounds 5a–f were prepared by reaction between 2-chloro-4- morpholinothiazol-5-carbaldehyde 3 and substituted acetophenones 4a–f. Treatment of compounds 5a–f with hydrazine hydrate employing mild reaction conditions led to the formation of 4,5-dihydro- 1H-pyrazoles 6a–f. Then the treatment with acetic anhydride or formic acid afforded the expected 4,5- dihydro-1H-pyrazoles 7a–f and 8a–f. The antifungal activity of each series of synthesized compounds was determined against the clinically important fungi Candida albicans and Cryptococcus neoformans. In addition, the most active compounds 7e and 7f were tested in combination with the commercial antifungal agents: fluconazole, itraconazole, and amphotericin B. Compound 7e showed a synergistic effect with fluconazole against C. albicans while 7f showed synergistic activities with all tested antifungal drugs against the same yeast
Fil: Ramirez, Juan. Universidad del Valle; Colombia
Fil: Rodriguez, Maria Victoria. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas; Argentina
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Sortino, Maximiliano Andrés. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina
Fil: Zacchino, Susana Alicia Stella. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Area Farmacognosia; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia
description The a,b-unsaturated carbonyl compounds 5a–f were prepared by reaction between 2-chloro-4- morpholinothiazol-5-carbaldehyde 3 and substituted acetophenones 4a–f. Treatment of compounds 5a–f with hydrazine hydrate employing mild reaction conditions led to the formation of 4,5-dihydro- 1H-pyrazoles 6a–f. Then the treatment with acetic anhydride or formic acid afforded the expected 4,5- dihydro-1H-pyrazoles 7a–f and 8a–f. The antifungal activity of each series of synthesized compounds was determined against the clinically important fungi Candida albicans and Cryptococcus neoformans. In addition, the most active compounds 7e and 7f were tested in combination with the commercial antifungal agents: fluconazole, itraconazole, and amphotericin B. Compound 7e showed a synergistic effect with fluconazole against C. albicans while 7f showed synergistic activities with all tested antifungal drugs against the same yeast
publishDate 2014
dc.date.none.fl_str_mv 2014-04
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/11336/29968
Ramirez, Juan; Rodriguez, Maria Victoria; Quiroga, Jairo; Abonia, Rodrigo; Sortino, Maximiliano Andrés; et al.; Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.; Wiley VCH Verlag; Archiv Der Pharmazie; 347; 8; 4-2014; 566-575
0365-6233
CONICET Digital
CONICET
url http://hdl.handle.net/11336/29968
identifier_str_mv Ramirez, Juan; Rodriguez, Maria Victoria; Quiroga, Jairo; Abonia, Rodrigo; Sortino, Maximiliano Andrés; et al.; Efficient synthesis under mild reaction conditions of novel 3-aryl-5-(4-chloro-2-morpholinothiazol-5-yl)-4,5-dihydro-1H-pyrazoles and their antifungal activity alone and in combination with commercial antifungal agents.; Wiley VCH Verlag; Archiv Der Pharmazie; 347; 8; 4-2014; 566-575
0365-6233
CONICET Digital
CONICET
dc.language.none.fl_str_mv eng
language eng
dc.relation.none.fl_str_mv info:eu-repo/semantics/altIdentifier/doi/10.1002/ardp.201400084
info:eu-repo/semantics/altIdentifier/url/http://onlinelibrary.wiley.com/doi/10.1002/ardp.201400084/abstract
dc.rights.none.fl_str_mv info:eu-repo/semantics/openAccess
https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
eu_rights_str_mv openAccess
rights_invalid_str_mv https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
dc.format.none.fl_str_mv application/pdf
application/pdf
dc.publisher.none.fl_str_mv Wiley VCH Verlag
publisher.none.fl_str_mv Wiley VCH Verlag
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_ 1846082778471333888
score 13.22299

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