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
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/29968
Ver los metadatos del registro completo
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oai:ri.conicet.gov.ar:11336/29968 |
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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 Técnicas2025-09-29T09:40:31Zoai: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:34982025-09-29 09:40:32.08CONICET 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_ |
1844613282423373824 |
score |
13.070432 |