(FBIOyF) Departamento de Química Orgánica - Artículos

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Examinando (FBIOyF) Departamento de Química Orgánica - Artículos por Autor "Aranaga, Carlos Andrés"

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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 Agents
    (MDPI, 2024-03-23) Moreno, Leydi M.; Quiroga, Jairo; Abonia, Rodrigo; Crespo Ortíz, María del Pilar; Aranaga, Carlos Andrés; Martínez-Martínez, Luis; Sortino, Maximiliano Andrés; Barreto, Mauricio; Burbano, María E.; Insuasty, Braulio; https://orcid.org/0000-0002-9451-3063; https://orcid.org/0000-0003-3256-0961; https://orcid.org/0000-0003-2160-5167; https://orcid.org/0000-0003-1806-657X; https://orcid.org/0000-0002-6091-4045; https://orcid.org/0000-0002-4271-1690; https://orcid.org/0000-0001-5361-4901; https://orcid.org/0000-0001-8371-3310
    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.