Browsing by Author "Zacchino, Susana"
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Item Synthesis and antifungal activity of nitrophenyl-pyrazole substituted Schiff bases(Elsevier B.V., 2022-04-05) Restrepo Acevedo, Andrés; Osorio, Nicolas; Giraldo López, Luis E.; D'Vries, Richard F.; Zacchino, Susana; Abonia, Rodrigo; Le Lagadec, Ronan; Cuenú Cabezas, FernandoThree new pyrazole-based azomethine isomers (2a-c) bearing a 2-, 3- or 4-nitrophenyl substituent were prepared in almost quantitative yields using environmentally friendly techniques such as solvent-free and microwave-assisted procedures. The compounds were fully characterized by standard analytical methods, including single-crystal X-ray diffraction crystallography for two of the three synthesized compounds. The calculated molecular orbitals distributions of the HOMO and LUMO show that the band gap energy can be tuned by the addition of a nitrophenyl group on the pyrazole moiety and therefore the electrophilic character and the reactivity of the Schiff bases. The relative position of the nitro group plays an important role on the antifungal activity against C. albicans as compound bearing the 2-nitrophenyl substituent (2a) was considerably more active than the other derivatives. In contrast, all three isomers presented a similar, limited, activity against C. neoformans. Molecular docking simulations showed that the most active compound 2a presented the lowest binding energy with 3PVK model protein. © 2021 Elsevier B.V.Item Synthesis of novel quinoline–based 4,5–dihydro–1H–pyrazoles as potential anticancer, antifungal, antibacterial and antiprotozoal agents(Elsevier Masson SAS, 2017-03-16) Ramírez Prada, Jonathan; Robledo, Sara M.; Velez, Ivan D.; Crespo, María del Pilar; Quiroga, Jairo; Abonia, Rodrigo; Montoya, Alba; Svetaz, Laura; Zacchino, Susana; Insuasty, BraulioA new series of Nesubstituted 2epyrazolines 9aef, 10aef, 11aef, 12aef and 13aef were obtained from the cyclocondensation reaction of [(7echloroquinoline4eyl)amino]chalcones 8aef 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 mM (0.13e6.05 mg/ mL) and LC50 values ranging from 2.6 to > 100 mM (1.2 to > 51.7 mg/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 mg/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 ¼ 7.8 mg/mL. For antiePlasmodium falciparum activity the 2epyrazoline 11b was the most active with EC50 ¼ 5.54 mg/mL. Regarding the activity against Trypanosoma cruzi, compound 10a was highly active with EC50 ¼ 0.70 mg/mL. Chalcone 8a had good activity against Leishmania panamensis amastigotes with EC50 ¼ 0.79 mg/mL.