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Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base)

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Center of Applied Nanosciences (CANS), Facultad de Ciencias Exactas, Universidad Andres Bello, República 330, Santiago 8370186, Chile
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FONDECYT de Inicio, Facultad de Ciencias Exactas, Universidad Andres Bello, República 330, Santiago 8370186, Chile
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Instituto de Ciencias Naturales, Facultad de Medicina Veterinaria y Agronomía, Universidad de Las Américas, Sede Providencia, Manuel Montt 948, Santiago 7500972, Chile
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Facultad de Ciencias de la Salud, Universidad Central de Chile, Lord Cochrane 417, Santiago 8330507, Chile
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Laboratorio de Genética y Patogénesis Bacteriana, Facultad de Ciencias de la Vida, Universidad Andres Bello, República 330, Santiago 8370186, Chile
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Facultad de Química y Biología, USACH, Av. L.B. O’Higgins 3363, Santiago 7254758, Chile
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Laboratorio de Análisis de Sólido (LAS), Facultad de Ingeniería y Facultad de Ciencias Exactas, Universidad Andrés Bello, República 330, Santiago 8370186, Chile
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Centro de Biotecnología Vegetal (CBV), Laboratorio de Fitopatógenos Fúngicos, Facultad de Ciencias de la Vida, Universidad Andres Bello, República 330, Santiago 8370186, Chile
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Escuela de Química y Farmacia, Facultad de Medicina, Universidad Andres Bello, República 252, Santiago 8320000, Chile
*
Authors to whom correspondence should be addressed.
Molecules 2020, 25(12), 2741; https://doi.org/10.3390/molecules25122741
Received: 5 May 2020 / Revised: 30 May 2020 / Accepted: 1 June 2020 / Published: 13 June 2020
(This article belongs to the Section Chemical Biology)
Botrytis cinerea is a ubiquitous necrotrophic filamentous fungal phytopathogen that lacks host specificity and can affect more than 1000 different plant species. In this work, we explored L1 [(E)-2-{[(2-aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol], a pyridine Schiff base harboring an intramolecular bond (IHB), regarding their antifungal activity against Botrytis cinerea. Moreover, we present a full characterization of the L1 by NMR and powder diffraction, as well as UV–vis, in the presence of previously untested different organic solvents. Complementary time-dependent density functional theory (TD-DFT) calculations were performed, and the noncovalent interaction (NCI) index was determined. Moreover, we obtained a scan-rate study on cyclic voltammetry of L1. Finally, we tested the antifungal activity of L1 against two strains of Botrytis cinerea (B05.10, a standard laboratory strain; and A1, a wild type strains isolated from Chilean blueberries). We found that L1 acts as an efficient antifungal agent against Botrytis cinerea at 26 °C, even better than the commercial antifungal agent fenhexamid. Although the antifungal activity was also observed at 4 °C, the effect was less pronounced. These results show the high versatility of this kind of pyridine Schiff bases in biological applications. View Full-Text
Keywords: Pyridine Schiff base; intramolecular hydrogen bond; Botrytis cinerea Pyridine Schiff base; intramolecular hydrogen bond; Botrytis cinerea
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MDPI and ACS Style

Carreño, A.; Páez-Hernández, D.; Cantero-López, P.; Zúñiga, C.; Nevermann, J.; Ramírez-Osorio, A.; Gacitúa, M.; Oyarzún, P.; Sáez-Cortez, F.; Polanco, R.; Otero, C.; Fuentes, J.A. Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base). Molecules 2020, 25, 2741. https://doi.org/10.3390/molecules25122741

AMA Style

Carreño A, Páez-Hernández D, Cantero-López P, Zúñiga C, Nevermann J, Ramírez-Osorio A, Gacitúa M, Oyarzún P, Sáez-Cortez F, Polanco R, Otero C, Fuentes JA. Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base). Molecules. 2020; 25(12):2741. https://doi.org/10.3390/molecules25122741

Chicago/Turabian Style

Carreño, Alexander; Páez-Hernández, Dayán; Cantero-López, Plinio; Zúñiga, César; Nevermann, Jan; Ramírez-Osorio, Angélica; Gacitúa, Manuel; Oyarzún, Poldie; Sáez-Cortez, Felipe; Polanco, Rubén; Otero, Carolina; Fuentes, Juan A. 2020. "Structural Characterization, DFT Calculation, NCI, Scan-Rate Analysis and Antifungal Activity against Botrytis cinerea of (E)-2-{[(2-Aminopyridin-2-yl)imino]-methyl}-4,6-di-tert-butylphenol (Pyridine Schiff Base)" Molecules 25, no. 12: 2741. https://doi.org/10.3390/molecules25122741

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