Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents
- Autores
- Ramirez Prada, Jonathan; Robledo, Sara M.; Velez, Ivan D.; Crespo, Maria del Pilar; Quiroga, Jairo; Abonia, Rodrigo; Montoya, Alba; Svetaz, Laura Andrea; Zacchino, Susana Alicia Stella; Insuasty, Braulio
- Año de publicación
- 2017
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- A new series of N–substituted 2–pyrazolines 9a–f, 10a–f, 11a–f, 12a–f and 13a–f were obtained from the cyclocondensation reaction of [(7–chloroquinolin–4–yl)amino]chalcones 8a–f with hydrazine hydrate and its derivatives. Fourteen of the synthesized compounds including the starting chalcones were selected by US National Cancer Institute (NCI) for testing their anticancer activity against 60 different human cancer cell lines, with the most important GI50 values ranging from 0.28 to 11.7 μM (0.13–6.05 μg/mL) and LC50 values ranging from 2.6 to > 100 μM (1.2 to > 51.7 μg/mL), for chalcones 8a,d and pyrazolines 10c,d. All compounds were assessed for antibacterial activity against wild type and multidrug resistant gram negative and gram positive bacteria, with MIC values ranging from 31.25 to 500 μg/mL. Additionally, the novel compounds were tested for antifungal and antiparasitic properties. Although these compounds showed mild activity against Candida albicans, chalcones 8a and 8e showed high activity against Cryptococcus neoformans with MIC50 = 7.8 μg/mL. For anti–Plasmodium falciparum activity the 2–pyrazoline 11b was the most active with EC50 = 5.54 μg/mL. Regarding the activity against Trypanosoma cruzi, compound 10a was highly active with EC50 = 0.70 μg/mL. Chalcone 8a had good activity against Leishmania panamensis amastigotes with EC50 = 0.79 μg/mL.
Fil: Ramirez Prada, Jonathan. Universidad del Valle; Colombia
Fil: Robledo, Sara M.. Universidad de Antioquia; Chile
Fil: Velez, Ivan D.. Universidad de Antioquia; Chile
Fil: Crespo, Maria del Pilar. Universidad del Valle; Colombia. Universidad Santiago de Cali; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Montoya, Alba. Universidad del Valle; Colombia
Fil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Insuasty, Braulio. Universidad del Valle; Colombia - Materia
-
2&Ndash;Pyrazolines
Antibacterial Activity
Anticancer Activity
Antifungal Activity
Antileishmanial Activity
Antimalarial Activity
Antitrypanosomal Activity
Chalcones
Quinoline - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by-nc-sa/2.5/ar/
- Repositorio
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/53154
Ver los metadatos del registro completo
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Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agentsRamirez Prada, JonathanRobledo, Sara M.Velez, Ivan D.Crespo, Maria del PilarQuiroga, JairoAbonia, RodrigoMontoya, AlbaSvetaz, Laura AndreaZacchino, Susana Alicia StellaInsuasty, Braulio2&Ndash;PyrazolinesAntibacterial ActivityAnticancer ActivityAntifungal ActivityAntileishmanial ActivityAntimalarial ActivityAntitrypanosomal ActivityChalconesQuinolinehttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1A new series of N–substituted 2–pyrazolines 9a–f, 10a–f, 11a–f, 12a–f and 13a–f were obtained from the cyclocondensation reaction of [(7–chloroquinolin–4–yl)amino]chalcones 8a–f with hydrazine hydrate and its derivatives. Fourteen of the synthesized compounds including the starting chalcones were selected by US National Cancer Institute (NCI) for testing their anticancer activity against 60 different human cancer cell lines, with the most important GI50 values ranging from 0.28 to 11.7 μM (0.13–6.05 μg/mL) and LC50 values ranging from 2.6 to > 100 μM (1.2 to > 51.7 μg/mL), for chalcones 8a,d and pyrazolines 10c,d. All compounds were assessed for antibacterial activity against wild type and multidrug resistant gram negative and gram positive bacteria, with MIC values ranging from 31.25 to 500 μg/mL. Additionally, the novel compounds were tested for antifungal and antiparasitic properties. Although these compounds showed mild activity against Candida albicans, chalcones 8a and 8e showed high activity against Cryptococcus neoformans with MIC50 = 7.8 μg/mL. For anti–Plasmodium falciparum activity the 2–pyrazoline 11b was the most active with EC50 = 5.54 μg/mL. Regarding the activity against Trypanosoma cruzi, compound 10a was highly active with EC50 = 0.70 μg/mL. Chalcone 8a had good activity against Leishmania panamensis amastigotes with EC50 = 0.79 μg/mL.Fil: Ramirez Prada, Jonathan. Universidad del Valle; ColombiaFil: Robledo, Sara M.. Universidad de Antioquia; ChileFil: Velez, Ivan D.. Universidad de Antioquia; ChileFil: Crespo, Maria del Pilar. Universidad del Valle; Colombia. Universidad Santiago de Cali; ColombiaFil: Quiroga, Jairo. Universidad del Valle; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Montoya, Alba. Universidad del Valle; ColombiaFil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Insuasty, Braulio. Universidad del Valle; ColombiaElsevier France-editions Scientifiques Medicales Elsevier2017-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/53154Ramirez Prada, Jonathan; Robledo, Sara M.; Velez, Ivan D.; Crespo, Maria del Pilar; Quiroga, Jairo; et al.; Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 131; 3-2017; 237-2540223-5234CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2017.03.016info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523417301733info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by-nc-sa/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-03T10:09:26Zoai:ri.conicet.gov.ar:11336/53154instacron: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:34982025-09-03 10:09:27.158CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| title |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| spellingShingle |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents Ramirez Prada, Jonathan 2&Ndash;Pyrazolines Antibacterial Activity Anticancer Activity Antifungal Activity Antileishmanial Activity Antimalarial Activity Antitrypanosomal Activity Chalcones Quinoline |
| title_short |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| title_full |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| title_fullStr |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| title_full_unstemmed |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| title_sort |
Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents |
| dc.creator.none.fl_str_mv |
Ramirez Prada, Jonathan Robledo, Sara M. Velez, Ivan D. Crespo, Maria del Pilar Quiroga, Jairo Abonia, Rodrigo Montoya, Alba Svetaz, Laura Andrea Zacchino, Susana Alicia Stella Insuasty, Braulio |
| author |
Ramirez Prada, Jonathan |
| author_facet |
Ramirez Prada, Jonathan Robledo, Sara M. Velez, Ivan D. Crespo, Maria del Pilar Quiroga, Jairo Abonia, Rodrigo Montoya, Alba Svetaz, Laura Andrea Zacchino, Susana Alicia Stella Insuasty, Braulio |
| author_role |
author |
| author2 |
Robledo, Sara M. Velez, Ivan D. Crespo, Maria del Pilar Quiroga, Jairo Abonia, Rodrigo Montoya, Alba Svetaz, Laura Andrea Zacchino, Susana Alicia Stella Insuasty, Braulio |
| author2_role |
author author author author author author author author author |
| dc.subject.none.fl_str_mv |
2&Ndash;Pyrazolines Antibacterial Activity Anticancer Activity Antifungal Activity Antileishmanial Activity Antimalarial Activity Antitrypanosomal Activity Chalcones Quinoline |
| topic |
2&Ndash;Pyrazolines Antibacterial Activity Anticancer Activity Antifungal Activity Antileishmanial Activity Antimalarial Activity Antitrypanosomal Activity Chalcones Quinoline |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
A new series of N–substituted 2–pyrazolines 9a–f, 10a–f, 11a–f, 12a–f and 13a–f were obtained from the cyclocondensation reaction of [(7–chloroquinolin–4–yl)amino]chalcones 8a–f with hydrazine hydrate and its derivatives. Fourteen of the synthesized compounds including the starting chalcones were selected by US National Cancer Institute (NCI) for testing their anticancer activity against 60 different human cancer cell lines, with the most important GI50 values ranging from 0.28 to 11.7 μM (0.13–6.05 μg/mL) and LC50 values ranging from 2.6 to > 100 μM (1.2 to > 51.7 μg/mL), for chalcones 8a,d and pyrazolines 10c,d. All compounds were assessed for antibacterial activity against wild type and multidrug resistant gram negative and gram positive bacteria, with MIC values ranging from 31.25 to 500 μg/mL. Additionally, the novel compounds were tested for antifungal and antiparasitic properties. Although these compounds showed mild activity against Candida albicans, chalcones 8a and 8e showed high activity against Cryptococcus neoformans with MIC50 = 7.8 μg/mL. For anti–Plasmodium falciparum activity the 2–pyrazoline 11b was the most active with EC50 = 5.54 μg/mL. Regarding the activity against Trypanosoma cruzi, compound 10a was highly active with EC50 = 0.70 μg/mL. Chalcone 8a had good activity against Leishmania panamensis amastigotes with EC50 = 0.79 μg/mL. Fil: Ramirez Prada, Jonathan. Universidad del Valle; Colombia Fil: Robledo, Sara M.. Universidad de Antioquia; Chile Fil: Velez, Ivan D.. Universidad de Antioquia; Chile Fil: Crespo, Maria del Pilar. Universidad del Valle; Colombia. Universidad Santiago de Cali; Colombia Fil: Quiroga, Jairo. Universidad del Valle; Colombia Fil: Abonia, Rodrigo. Universidad del Valle; Colombia Fil: Montoya, Alba. Universidad del Valle; Colombia Fil: Svetaz, Laura Andrea. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina Fil: Zacchino, Susana Alicia Stella. Consejo Nacional de Investigaciones Científicas y Técnicas; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina Fil: Insuasty, Braulio. Universidad del Valle; Colombia |
| description |
A new series of N–substituted 2–pyrazolines 9a–f, 10a–f, 11a–f, 12a–f and 13a–f were obtained from the cyclocondensation reaction of [(7–chloroquinolin–4–yl)amino]chalcones 8a–f with hydrazine hydrate and its derivatives. Fourteen of the synthesized compounds including the starting chalcones were selected by US National Cancer Institute (NCI) for testing their anticancer activity against 60 different human cancer cell lines, with the most important GI50 values ranging from 0.28 to 11.7 μM (0.13–6.05 μg/mL) and LC50 values ranging from 2.6 to > 100 μM (1.2 to > 51.7 μg/mL), for chalcones 8a,d and pyrazolines 10c,d. All compounds were assessed for antibacterial activity against wild type and multidrug resistant gram negative and gram positive bacteria, with MIC values ranging from 31.25 to 500 μg/mL. Additionally, the novel compounds were tested for antifungal and antiparasitic properties. Although these compounds showed mild activity against Candida albicans, chalcones 8a and 8e showed high activity against Cryptococcus neoformans with MIC50 = 7.8 μg/mL. For anti–Plasmodium falciparum activity the 2–pyrazoline 11b was the most active with EC50 = 5.54 μg/mL. Regarding the activity against Trypanosoma cruzi, compound 10a was highly active with EC50 = 0.70 μg/mL. Chalcone 8a had good activity against Leishmania panamensis amastigotes with EC50 = 0.79 μg/mL. |
| publishDate |
2017 |
| dc.date.none.fl_str_mv |
2017-03 |
| 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/11336/53154 Ramirez Prada, Jonathan; Robledo, Sara M.; Velez, Ivan D.; Crespo, Maria del Pilar; Quiroga, Jairo; et al.; Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 131; 3-2017; 237-254 0223-5234 CONICET Digital CONICET |
| url |
http://hdl.handle.net/11336/53154 |
| identifier_str_mv |
Ramirez Prada, Jonathan; Robledo, Sara M.; Velez, Ivan D.; Crespo, Maria del Pilar; Quiroga, Jairo; et al.; Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents; Elsevier France-editions Scientifiques Medicales Elsevier; European Journal of Medical Chemistry; 131; 3-2017; 237-254 0223-5234 CONICET Digital CONICET |
| dc.language.none.fl_str_mv |
eng |
| language |
eng |
| dc.relation.none.fl_str_mv |
info:eu-repo/semantics/altIdentifier/doi/10.1016/j.ejmech.2017.03.016 info:eu-repo/semantics/altIdentifier/url/https://www.sciencedirect.com/science/article/pii/S0223523417301733 |
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info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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openAccess |
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https://creativecommons.org/licenses/by-nc-sa/2.5/ar/ |
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application/pdf application/pdf |
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Elsevier France-editions Scientifiques Medicales Elsevier |
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Elsevier France-editions Scientifiques Medicales Elsevier |
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Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicas |
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dasensio@conicet.gov.ar; lcarlino@conicet.gov.ar |
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