Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents
- Autores
- Moreno, Leydi M.; Quiroga, Jairo; Abonia, Rodrigo; Crespo, María del P.; Aranaga, Carlos; Martínez Martínez, Luis; Sortino, Maximiliano Andrés; Barreto, Mauricio; Burbano, María E.; Insuasty, Braulio
- Año de publicación
- 2024
- Idioma
- inglés
- Tipo de recurso
- artículo
- Estado
- versión publicada
- Descripción
- This study presents the synthesis of four series of novel hybrid chalcones (20,21)a–g and (23,24)a–g and six series of 1,3,5-triazine-based pyrimido[4,5-b][1,4]diazepines (28–33)a–g and the evaluation of their anticancer, antibacterial, antifungal, and cytotoxic properties. Chalcones 20b,d, 21a,b,d, 23a,d–g, 24a–g and the pyrimido[4,5-b][1,4]diazepines 29e,g, 30g, 31a,b,e–g, 33a,b,e–g exhibited outstanding anticancer activity against a panel of 60 cancer cell lines with GI50 values between 0.01 and 100 μM and LC50 values in the range of 4.09 μM to >100 μM, several of such derivatives showing higher activity than the standard drug 5-fluorouracil (5-FU). On the other hand, among the synthesized compounds, the best antibacterial properties against N. gonorrhoeae, S. aureus (ATCC 43300), and M. tuberculosis were exhibited by the pyrimido[4,5-b][1,4]diazepines (MICs: 0.25–62.5 µg/mL). The antifungal activity studies showed that triazinylamino-chalcone 29e and triazinyloxy-chalcone 31g were the most active compounds against T. rubrum and T. mentagrophytes and A. fumigatus, respectively (MICs = 62.5 μg/mL). Hemolytic activity studies and in silico toxicity analysis demonstrated that most of the compounds are safe.
Fil: Moreno, Leydi M.. Universidad del Valle; Colombia
Fil: Quiroga, Jairo. Universidad del Valle; Colombia
Fil: Abonia, Rodrigo. Universidad del Valle; Colombia
Fil: Crespo, María del P.. Universidad del Valle; Colombia
Fil: Aranaga, Carlos. Universidad de Santiago de Cali; Colombia. Universidad de Córdoba; España
Fil: Martínez Martínez, Luis. Universidad de Córdoba; España
Fil: Sortino, Maximiliano Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina
Fil: Barreto, Mauricio. Universidad del Valle; Colombia
Fil: Burbano, María E.. Universidad del Valle; Colombia
Fil: Insuasty, Braulio. Grupo de Investigación de Compuestos Heterocíclicos; Colombia - Materia
-
1,3,5-TRIAZINES
CHALCONES
DIAZEPINES
ANTICANCER ACTIVITY
ANTIBACTERIAL ACTIVITY
ANTIFUNGAL ACTIVITY
CYTOTOXICITY - Nivel de accesibilidad
- acceso abierto
- Condiciones de uso
- https://creativecommons.org/licenses/by/2.5/ar/
- Repositorio
.jpg)
- Institución
- Consejo Nacional de Investigaciones Científicas y Técnicas
- OAI Identificador
- oai:ri.conicet.gov.ar:11336/233592
Ver los metadatos del registro completo
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Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal AgentsMoreno, Leydi M.Quiroga, JairoAbonia, RodrigoCrespo, María del P.Aranaga, CarlosMartínez Martínez, LuisSortino, Maximiliano AndrésBarreto, MauricioBurbano, María E.Insuasty, Braulio1,3,5-TRIAZINESCHALCONESDIAZEPINESANTICANCER ACTIVITYANTIBACTERIAL ACTIVITYANTIFUNGAL ACTIVITYCYTOTOXICITYhttps://purl.org/becyt/ford/1.4https://purl.org/becyt/ford/1This study presents the synthesis of four series of novel hybrid chalcones (20,21)a–g and (23,24)a–g and six series of 1,3,5-triazine-based pyrimido[4,5-b][1,4]diazepines (28–33)a–g and the evaluation of their anticancer, antibacterial, antifungal, and cytotoxic properties. Chalcones 20b,d, 21a,b,d, 23a,d–g, 24a–g and the pyrimido[4,5-b][1,4]diazepines 29e,g, 30g, 31a,b,e–g, 33a,b,e–g exhibited outstanding anticancer activity against a panel of 60 cancer cell lines with GI50 values between 0.01 and 100 μM and LC50 values in the range of 4.09 μM to >100 μM, several of such derivatives showing higher activity than the standard drug 5-fluorouracil (5-FU). On the other hand, among the synthesized compounds, the best antibacterial properties against N. gonorrhoeae, S. aureus (ATCC 43300), and M. tuberculosis were exhibited by the pyrimido[4,5-b][1,4]diazepines (MICs: 0.25–62.5 µg/mL). The antifungal activity studies showed that triazinylamino-chalcone 29e and triazinyloxy-chalcone 31g were the most active compounds against T. rubrum and T. mentagrophytes and A. fumigatus, respectively (MICs = 62.5 μg/mL). Hemolytic activity studies and in silico toxicity analysis demonstrated that most of the compounds are safe.Fil: Moreno, Leydi M.. Universidad del Valle; ColombiaFil: Quiroga, Jairo. Universidad del Valle; ColombiaFil: Abonia, Rodrigo. Universidad del Valle; ColombiaFil: Crespo, María del P.. Universidad del Valle; ColombiaFil: Aranaga, Carlos. Universidad de Santiago de Cali; Colombia. Universidad de Córdoba; EspañaFil: Martínez Martínez, Luis. Universidad de Córdoba; EspañaFil: Sortino, Maximiliano Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; ArgentinaFil: Barreto, Mauricio. Universidad del Valle; ColombiaFil: Burbano, María E.. Universidad del Valle; ColombiaFil: Insuasty, Braulio. Grupo de Investigación de Compuestos Heterocíclicos; ColombiaMolecular Diversity Preservation International2024-03info:eu-repo/semantics/articleinfo:eu-repo/semantics/publishedVersionhttp://purl.org/coar/resource_type/c_6501info:ar-repo/semantics/articuloapplication/pdfapplication/pdfhttp://hdl.handle.net/11336/233592Moreno, Leydi M.; Quiroga, Jairo; Abonia, Rodrigo; Crespo, María del P.; Aranaga, Carlos; et al.; Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents; Molecular Diversity Preservation International; International Journal of Molecular Sciences; 25; 7; 3-2024; 1-241422-0067CONICET DigitalCONICETenginfo:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1422-0067/25/7/3623info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms25073623info:eu-repo/semantics/openAccesshttps://creativecommons.org/licenses/by/2.5/ar/reponame:CONICET Digital (CONICET)instname:Consejo Nacional de Investigaciones Científicas y Técnicas2025-09-10T13:07:44Zoai:ri.conicet.gov.ar:11336/233592instacron: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:34982025-09-10 13:07:45.126CONICET Digital (CONICET) - Consejo Nacional de Investigaciones Científicas y Técnicasfalse |
| dc.title.none.fl_str_mv |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| title |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| spellingShingle |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents Moreno, Leydi M. 1,3,5-TRIAZINES CHALCONES DIAZEPINES ANTICANCER ACTIVITY ANTIBACTERIAL ACTIVITY ANTIFUNGAL ACTIVITY CYTOTOXICITY |
| title_short |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| title_full |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| title_fullStr |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| title_full_unstemmed |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| title_sort |
Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents |
| dc.creator.none.fl_str_mv |
Moreno, Leydi M. Quiroga, Jairo Abonia, Rodrigo Crespo, María del P. Aranaga, Carlos Martínez Martínez, Luis Sortino, Maximiliano Andrés Barreto, Mauricio Burbano, María E. Insuasty, Braulio |
| author |
Moreno, Leydi M. |
| author_facet |
Moreno, Leydi M. Quiroga, Jairo Abonia, Rodrigo Crespo, María del P. Aranaga, Carlos Martínez Martínez, Luis Sortino, Maximiliano Andrés Barreto, Mauricio Burbano, María E. Insuasty, Braulio |
| author_role |
author |
| author2 |
Quiroga, Jairo Abonia, Rodrigo Crespo, María del P. Aranaga, Carlos Martínez Martínez, Luis Sortino, Maximiliano Andrés Barreto, Mauricio Burbano, María E. Insuasty, Braulio |
| author2_role |
author author author author author author author author author |
| dc.subject.none.fl_str_mv |
1,3,5-TRIAZINES CHALCONES DIAZEPINES ANTICANCER ACTIVITY ANTIBACTERIAL ACTIVITY ANTIFUNGAL ACTIVITY CYTOTOXICITY |
| topic |
1,3,5-TRIAZINES CHALCONES DIAZEPINES ANTICANCER ACTIVITY ANTIBACTERIAL ACTIVITY ANTIFUNGAL ACTIVITY CYTOTOXICITY |
| purl_subject.fl_str_mv |
https://purl.org/becyt/ford/1.4 https://purl.org/becyt/ford/1 |
| dc.description.none.fl_txt_mv |
This study presents the synthesis of four series of novel hybrid chalcones (20,21)a–g and (23,24)a–g and six series of 1,3,5-triazine-based pyrimido[4,5-b][1,4]diazepines (28–33)a–g and the evaluation of their anticancer, antibacterial, antifungal, and cytotoxic properties. Chalcones 20b,d, 21a,b,d, 23a,d–g, 24a–g and the pyrimido[4,5-b][1,4]diazepines 29e,g, 30g, 31a,b,e–g, 33a,b,e–g exhibited outstanding anticancer activity against a panel of 60 cancer cell lines with GI50 values between 0.01 and 100 μM and LC50 values in the range of 4.09 μM to >100 μM, several of such derivatives showing higher activity than the standard drug 5-fluorouracil (5-FU). On the other hand, among the synthesized compounds, the best antibacterial properties against N. gonorrhoeae, S. aureus (ATCC 43300), and M. tuberculosis were exhibited by the pyrimido[4,5-b][1,4]diazepines (MICs: 0.25–62.5 µg/mL). The antifungal activity studies showed that triazinylamino-chalcone 29e and triazinyloxy-chalcone 31g were the most active compounds against T. rubrum and T. mentagrophytes and A. fumigatus, respectively (MICs = 62.5 μg/mL). Hemolytic activity studies and in silico toxicity analysis demonstrated that most of the compounds are safe. Fil: Moreno, Leydi M.. Universidad del Valle; Colombia Fil: Quiroga, Jairo. Universidad del Valle; Colombia Fil: Abonia, Rodrigo. Universidad del Valle; Colombia Fil: Crespo, María del P.. Universidad del Valle; Colombia Fil: Aranaga, Carlos. Universidad de Santiago de Cali; Colombia. Universidad de Córdoba; España Fil: Martínez Martínez, Luis. Universidad de Córdoba; España Fil: Sortino, Maximiliano Andrés. Consejo Nacional de Investigaciones Científicas y Técnicas. Centro Científico Tecnológico Conicet - Rosario; Argentina. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Departamento de Química Orgánica. Área Farmacognosia; Argentina Fil: Barreto, Mauricio. Universidad del Valle; Colombia Fil: Burbano, María E.. Universidad del Valle; Colombia Fil: Insuasty, Braulio. Grupo de Investigación de Compuestos Heterocíclicos; Colombia |
| description |
This study presents the synthesis of four series of novel hybrid chalcones (20,21)a–g and (23,24)a–g and six series of 1,3,5-triazine-based pyrimido[4,5-b][1,4]diazepines (28–33)a–g and the evaluation of their anticancer, antibacterial, antifungal, and cytotoxic properties. Chalcones 20b,d, 21a,b,d, 23a,d–g, 24a–g and the pyrimido[4,5-b][1,4]diazepines 29e,g, 30g, 31a,b,e–g, 33a,b,e–g exhibited outstanding anticancer activity against a panel of 60 cancer cell lines with GI50 values between 0.01 and 100 μM and LC50 values in the range of 4.09 μM to >100 μM, several of such derivatives showing higher activity than the standard drug 5-fluorouracil (5-FU). On the other hand, among the synthesized compounds, the best antibacterial properties against N. gonorrhoeae, S. aureus (ATCC 43300), and M. tuberculosis were exhibited by the pyrimido[4,5-b][1,4]diazepines (MICs: 0.25–62.5 µg/mL). The antifungal activity studies showed that triazinylamino-chalcone 29e and triazinyloxy-chalcone 31g were the most active compounds against T. rubrum and T. mentagrophytes and A. fumigatus, respectively (MICs = 62.5 μg/mL). Hemolytic activity studies and in silico toxicity analysis demonstrated that most of the compounds are safe. |
| publishDate |
2024 |
| dc.date.none.fl_str_mv |
2024-03 |
| 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/11336/233592 Moreno, Leydi M.; Quiroga, Jairo; Abonia, Rodrigo; Crespo, María del P.; Aranaga, Carlos; et al.; Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents; Molecular Diversity Preservation International; International Journal of Molecular Sciences; 25; 7; 3-2024; 1-24 1422-0067 CONICET Digital CONICET |
| url |
http://hdl.handle.net/11336/233592 |
| identifier_str_mv |
Moreno, Leydi M.; Quiroga, Jairo; Abonia, Rodrigo; Crespo, María del P.; Aranaga, Carlos; et al.; Synthesis of Novel Triazine-Based Chalcones and 8,9-dihydro-7H-pyrimido[4,5-b][1,4]diazepines as Potential Leads in the Search of Anticancer, Antibacterial and Antifungal Agents; Molecular Diversity Preservation International; International Journal of Molecular Sciences; 25; 7; 3-2024; 1-24 1422-0067 CONICET Digital CONICET |
| dc.language.none.fl_str_mv |
eng |
| language |
eng |
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info:eu-repo/semantics/altIdentifier/url/https://www.mdpi.com/1422-0067/25/7/3623 info:eu-repo/semantics/altIdentifier/doi/10.3390/ijms25073623 |
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info:eu-repo/semantics/openAccess https://creativecommons.org/licenses/by/2.5/ar/ |
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openAccess |
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https://creativecommons.org/licenses/by/2.5/ar/ |
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application/pdf application/pdf |
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Molecular Diversity Preservation International |
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Molecular Diversity Preservation International |
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reponame:CONICET Digital (CONICET) instname:Consejo Nacional de Investigaciones Científicas y Técnicas |
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CONICET Digital (CONICET) |
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CONICET Digital (CONICET) |
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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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12.993085 |