Restrepo Acevedo, AndrésOsorio, NicolasGiraldo López, Luis E.D'Vries, Richard F.Zacchino, SusanaAbonia, RodrigoLe Lagadec, RonanCuenú Cabezas, Fernando2025-06-062025-06-062022-04-05Restrepo-Acevedo, A., Osorio, N., Giraldo-López, L. E., D’Vries, R. F., Zacchino, S., Abonia, R., le Lagadec, R., & Cuenú-Cabezas, F. (2022). Synthesis and antifungal activity of nitrophenyl-pyrazole substituted Schiff bases. Journal of Molecular Structure, 1253. https://doi.org/10.1016/j.molstruc.2021.13228900222860https://repositorio.usc.edu.co/handle/20.500.12421/6974Three 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.enAb initio calculationsAntifungal agentsNitrogen heterocyclesNitrophenylSchiff basesArticle