Browsing by Author "Barreto, Mauricio"
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Item Pyrrolizine- and Indolizine-Derived Spirooxindoles: Synthesis, Antibacterial Activity and Inverse Docking Analysis(Multidisciplinary Digital Publishing Institute (MDPI), 2025-02-01) Romo, Pablo; Crespo, María del Pilar; Barreto, Mauricio; Burbano, María Elena; Mejia Gutierrez, Melissa; Quiroga, Jairo; Abonia, RodrigoSpirooxindoles are a family of heterocyclic compounds which bear the oxindole nucleus in their structures, which have a considerable pharmaceutical potential and which have been linked to various drugs for the treatment of diverse diseases. In this work, a wide variety of spirooxindoles bearing a pyrrolizinic nucleus were obtained by a 1,3-dipolar cycloaddition reaction between substituted isatins, trans-3-benzoyl acrylic acid and L-proline. In this approach, the target products 9a–m were obtained in 40–86% yields under heating to reflux in methanol over 2 h. Similarly, spirooxindoles containing an indolizinic nucleus 11a–j were obtained in 45–69% yields by switching L-proline for pipecolic acid under heating to reflux in acetonitrile for 8 h. The antibacterial activity of the obtained products was evaluated against P. aeruginosa, K. pneumoniae, E. coli, S. aureus, and N. gonorrhoeae, also including an inverse docking analysis. Results show that 9f and 11i, were the most active compounds against S. aureus, while compounds 9d and 9m displayed the higher activity against N. gonorrhoeae. Inverse docking analysis showed that compounds 9b, 11a 11e, and 11i displayed high affinity to the target protein 6TYM and 7Q6S, which are involved in biological pathways of diverse cancer and Parkinson diseases.Item 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) Moreno, Leydi M.; Quiroga, Jairo; Abonia, Rodrigo; Crespo, María del P.; Aranaga, Carlos; Martínez Martínez, Luis; Sortino, Maximiliano; Barreto, Mauricio; Burbano, María E.; Insuasty, BraulioThis 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.