Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN2(PhOH)CHN(C3N2(CH3)3)PhR, R = H or NO2)

Fernandez, Dorancelly; Restrepo-Acevedo, Andrés; Rocha-Roa, Cristian; Le Lagadec, Ronan; Abonia, Rodrigo; Zacchino, Susana; Gómez Castaño, Jovanny A.; Cuenú-Cabezas, Fernando

Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN2(PhOH)CHN(C3N2(CH3)3)PhR, R = H or NO2)

dc.citation.title	Molecules	es
dc.citation.volume	26
dc.creator	Fernandez, Dorancelly
dc.creator	Restrepo-Acevedo, Andrés
dc.creator	Rocha-Roa, Cristian
dc.creator	Le Lagadec, Ronan
dc.creator	Abonia, Rodrigo
dc.creator	Zacchino, Susana
dc.creator	Gómez Castaño, Jovanny A.
dc.creator	Cuenú-Cabezas, Fernando
dc.date.accessioned	2022-04-07T19:02:23Z
dc.date.available	2022-04-07T19:02:23Z
dc.date.issued	2021-12-08
dc.description	The azo-azomethine imines, R1-N=N-R2-CH=N-R3, are a class of active pharmacological ligands that have been prominent antifungal, antibacterial, and antitumor agents. In this study, four new azo-azomethines, R1 = Ph, R2 = phenol, and R3 = pyrazol-Ph-R’ (R = H or NO2), have been synthesized, structurally characterized using X-ray, IR, NMR and UV–Vis techniques, and their antifungal activity evaluated against certified strains of Candida albicans and Cryptococcus neoformans. The antifungal tests revealed a high to moderate inhibitory activity towards both strains, which is regulated as a function of both the presence and the location of the nitro group in the aromatic ring of the series. These biological assays were further complemented with molecular docking studies against three different molecular targets from each fungus strain. Molecular dynamics simulations and binding free energy calculations were performed on the two best molecular docking results for each fungus strain. Better affinity for active sites for nitro compounds at the “meta” and “para” positions was found, making them promising building blocks for the development of new Schiff bases with high antifungal activity.	es
dc.description.fil	Fil: Fernandez, Dorancelly. Universidad del Quindío. Programa de Química. Laboratorio de Química Inorgánica y Catálisis; Colombia.	es
dc.description.fil	Fil: Restrepo-Acevedo, Andrés. Universidad Nacional Autónoma de México. Instituto de Química; México.	es
dc.description.fil	Fil: Rocha-Roa, Cristian. Universidad del Quindío. Centro de Investigaciones Biomédicas. Grupo GEPAMOL; Colombia.	es
dc.description.fil	Fil: Rocha-Roa, Cristian. Universidad de Antioquia. Biophysics of Tropical Diseases. Max Planck Tandem Group; Colombia.	es
dc.description.fil	Fil: Le Lagadec, Ronan. Universidad Nacional Autónoma de México. Instituto de Química; México.	es
dc.description.fil	Fil: Abonia, Rodrigo. Universidad del Valle. Departamento de Química; Colombia.	es
dc.description.fil	Fil: Zacchino, Susana. Universidad Nacional de Rosario. Facultad de Ciencias Bioquímicas y Farmacéuticas. Área Farmacognosia; Rosario.	es
dc.description.fil	Fil: Gómez Castaño, Jovanny A. Universidad Pedagógica y Tecnológica de Colombia. Facultad de Ciencias. rupo Química-Física Molecular y Modelamiento Computacional (QUIMOL®); Colombia.	es
dc.description.fil	Fil: Cuenú-Cabezas, Fernando. Universidad del Quindío. Programa de Química. Laboratorio de Química Inorgánica y Catálisis; Colombia.	es
dc.description.sponsorship	Universidad del Quindío
dc.description.sponsorship	Institute of Chemistry at UNAM
dc.description.sponsorship	Universidad Pedagógica y Tecnológica de Colombia (UPTC)
dc.format	application/pdf
dc.format.extent	1-25	es
dc.identifier.issn	1420-3049	es
dc.identifier.uri	http://hdl.handle.net/2133/23341
dc.language.iso	eng	es
dc.publisher	MDPI	es
dc.relation.publisherversion	https://doi.org/10.3390/molecules26247435
dc.relation.publisherversion	https://www.mdpi.com/1420-3049/26/24/7435
dc.rights	openAccess	es
dc.rights.holder	Fernandez, Dorancelly	es
dc.rights.holder	Restrepo-Acevedo, Andrés	es
dc.rights.holder	Rocha-Roa, Cristian	es
dc.rights.holder	Le Lagadec, Ronan	es
dc.rights.holder	Abonia, Rodrigo	es
dc.rights.holder	Zacchino, Susana	es
dc.rights.holder	Gómez Castaño, Jovanny A.	es
dc.rights.holder	Cuenú-Cabezas, Fernando	es
dc.rights.text	Attribution 4.0 International (CC BY 4.0)	es
dc.rights.uri	http://creativecommons.org/licenses/by/2.5/ar/	*
dc.subject	Schiff bases	es
dc.subject	Azomethine compounds	es
dc.subject	Candida albicans	es
dc.subject	Cryptococcus neoformans	es
dc.subject	In silico studies	es
dc.subject	Molecular docking	es
dc.subject	QTAIM-C	es
dc.title	Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN2(PhOH)CHN(C3N2(CH3)3)PhR, R = H or NO2)	es
dc.type	publishedVersion
dc.type	article
dc.type	artículo
dc.type.collection	articulo
dc.type.version	publishedVersion

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