Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>)
The azo-azomethine imines, R<sup>1</sup>-N=N-R<sup>2</sup>-CH=N-R<sup>3</sup>, are a class of active pharmacological ligands that have been prominent antifungal, antibacterial, and antitumor agents. In this study, four new azo-azomethines, R<sup>1</sup>...
| Main Authors: | , , , , , , , |
|---|---|
| Format: | Article |
| Language: | English |
| Published: |
MDPI AG
2021-12-01
|
| Series: | Molecules |
| Subjects: | |
| Online Access: | https://www.mdpi.com/1420-3049/26/24/7435 |
| _version_ | 1797502203953414144 |
|---|---|
| author | Dorancelly Fernandez Andrés Restrepo-Acevedo Cristian Rocha-Roa Ronan Le Lagadec Rodrigo Abonia Susana A. Zacchino Jovanny A. Gómez Castaño Fernando Cuenú-Cabezas |
| author_facet | Dorancelly Fernandez Andrés Restrepo-Acevedo Cristian Rocha-Roa Ronan Le Lagadec Rodrigo Abonia Susana A. Zacchino Jovanny A. Gómez Castaño Fernando Cuenú-Cabezas |
| author_sort | Dorancelly Fernandez |
| collection | DOAJ |
| description | The azo-azomethine imines, R<sup>1</sup>-N=N-R<sup>2</sup>-CH=N-R<sup>3</sup>, are a class of active pharmacological ligands that have been prominent antifungal, antibacterial, and antitumor agents. In this study, four new azo-azomethines, R<sup>1</sup> = Ph, R<sup>2</sup> = phenol, and R<sup>3</sup> = pyrazol-Ph-R’ (R = H or NO<sub>2</sub>), have been synthesized, structurally characterized using X-ray, IR, NMR and UV–Vis techniques, and their antifungal activity evaluated against certified strains of <i>Candida albicans</i> and <i>Cryptococcus neoformans</i>. 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 “<i>meta</i>” and “<i>para</i>” positions was found, making them promising building blocks for the development of new Schiff bases with high antifungal activity. |
| first_indexed | 2024-03-10T03:29:36Z |
| format | Article |
| id | doaj.art-bfdaf89b90d5430ea8c6c1f89a02e183 |
| institution | Directory Open Access Journal |
| issn | 1420-3049 |
| language | English |
| last_indexed | 2024-03-10T03:29:36Z |
| publishDate | 2021-12-01 |
| publisher | MDPI AG |
| record_format | Article |
| series | Molecules |
| spelling | doaj.art-bfdaf89b90d5430ea8c6c1f89a02e1832023-11-23T09:43:58ZengMDPI AGMolecules1420-30492021-12-012624743510.3390/molecules26247435Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>)Dorancelly Fernandez0Andrés Restrepo-Acevedo1Cristian Rocha-Roa2Ronan Le Lagadec3Rodrigo Abonia4Susana A. Zacchino5Jovanny A. Gómez Castaño6Fernando Cuenú-Cabezas7Laboratorio de Química Inorgánica y Catálisis, Programa de Química, Universidad del Quindío, Carrera 15, Calle 12 Norte, Armenia 630004, ColombiaInstituto de Química UNAM, Circuito Exterior s/n, Ciudad Universitaria, Ciudad de México 04510, MexicoGrupo GEPAMOL, Centro de Investigaciones Biomédicas, Universidad del Quindío, Carrera 15, Calle 12 Norte, Armenia 630004, ColombiaInstituto de Química UNAM, Circuito Exterior s/n, Ciudad Universitaria, Ciudad de México 04510, MexicoDepartamento de Química, Universidad del Valle, Calle 13 No. 100-00, A.A. 25360, Cali 76001, ColombiaÁrea Farmacognosia, Facultad de Ciencias Bioquímicas y Farmacéuticas, Universidad Nacional de Rosario (UNR), Suipacha 531, Rosario S2002LRK, ArgentinaGrupo Química-Física Molecular y Modelamiento Computacional (QUIMOL®), Facultad de Ciencias, Universidad Pedagógica y Tecnológica de Colombia (UPTC), Avenida Central del Norte, Tunja, Boyacá 050030, ColombiaLaboratorio de Química Inorgánica y Catálisis, Programa de Química, Universidad del Quindío, Carrera 15, Calle 12 Norte, Armenia 630004, ColombiaThe azo-azomethine imines, R<sup>1</sup>-N=N-R<sup>2</sup>-CH=N-R<sup>3</sup>, are a class of active pharmacological ligands that have been prominent antifungal, antibacterial, and antitumor agents. In this study, four new azo-azomethines, R<sup>1</sup> = Ph, R<sup>2</sup> = phenol, and R<sup>3</sup> = pyrazol-Ph-R’ (R = H or NO<sub>2</sub>), have been synthesized, structurally characterized using X-ray, IR, NMR and UV–Vis techniques, and their antifungal activity evaluated against certified strains of <i>Candida albicans</i> and <i>Cryptococcus neoformans</i>. 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 “<i>meta</i>” and “<i>para</i>” positions was found, making them promising building blocks for the development of new Schiff bases with high antifungal activity.https://www.mdpi.com/1420-3049/26/24/7435Schiff basesazomethine compounds<i>Candida albicans</i><i>Cryptococcus neoformans</i>in silico studiesmolecular docking |
| spellingShingle | Dorancelly Fernandez Andrés Restrepo-Acevedo Cristian Rocha-Roa Ronan Le Lagadec Rodrigo Abonia Susana A. Zacchino Jovanny A. Gómez Castaño Fernando Cuenú-Cabezas Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>) Molecules Schiff bases azomethine compounds <i>Candida albicans</i> <i>Cryptococcus neoformans</i> in silico studies molecular docking |
| title | Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>) |
| title_full | Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>) |
| title_fullStr | Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>) |
| title_full_unstemmed | Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>) |
| title_short | Synthesis, Structural Characterization, and In Vitro and In Silico Antifungal Evaluation of Azo-Azomethine Pyrazoles (PhN<sub>2</sub>(PhOH)CHN(C<sub>3</sub>N<sub>2</sub>(CH<sub>3</sub>)<sub>3</sub>)PhR, R = H or NO<sub>2</sub>) |
| title_sort | synthesis structural characterization and in vitro and in silico antifungal evaluation of azo azomethine pyrazoles phn sub 2 sub phoh chn c sub 3 sub n sub 2 sub ch sub 3 sub sub 3 sub phr r h or no sub 2 sub |
| topic | Schiff bases azomethine compounds <i>Candida albicans</i> <i>Cryptococcus neoformans</i> in silico studies molecular docking |
| url | https://www.mdpi.com/1420-3049/26/24/7435 |
| work_keys_str_mv | AT dorancellyfernandez synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT andresrestrepoacevedo synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT cristianrocharoa synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT ronanlelagadec synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT rodrigoabonia synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT susanaazacchino synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT jovannyagomezcastano synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub AT fernandocuenucabezas synthesisstructuralcharacterizationandinvitroandinsilicoantifungalevaluationofazoazomethinepyrazolesphnsub2subphohchncsub3subnsub2subchsub3subsub3subphrrhornosub2sub |