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Molecules 2018, 23(6), 1377; https://doi.org/10.3390/molecules23061377

Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis

1
Escuela de Obstetricia y Puericultura, Facultad de medicina, Campus de la Salud, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, Chile
2
Institute of Food Science and Technology, University Austral of Chile, Valdivia 5090000, Chile
3
Centro de Investigaciones Biomédicas (CIB), Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso 2340000, Chile
4
Departamento De Ciencias Básicas, Campus Fernando May Universidad del Biobío, Avda. Andrés Bello s/n casilla 447, Chillán 3780000, Chile
5
Instituto de Química, Facultad de Ciencias, Pontificia Universidad Católica de Valparaíso, Av. Universidad #330, Curauma, Valparaíso 2340000, Chile
6
Centro de Biotecnología “Dr. Daniel Alkalay Lowitt”, Universidad Técnica Federico Santa María, Avda. España 1680, Valparaíso 2340000, Chile
7
Centro de Investigación Australbiotech, Universidad Santo Tomás, Avda. Ejército 146, Santiago 8320000, Chile
8
Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile
*
Author to whom correspondence should be addressed.
Received: 7 May 2018 / Revised: 30 May 2018 / Accepted: 3 June 2018 / Published: 7 June 2018
(This article belongs to the Section Organic Chemistry)
Full-Text   |   PDF [820 KB, uploaded 7 June 2018]   |  

Abstract

To investigate the anti-Saprolegnia activities of chalconic compounds, nine dialkoxychalcones 210, along with their key building block 2′,4′-dihydroxychalcone 1, were evaluated for their potential oomycide activities against Saprolegnia australis strains. The synthesis afforded a series of O-alkylated derivatives with typical chalcone skeletons. Compounds 410 were reported for the first time. Interestingly, analogue 8 with the new scaffold demonstrated remarkable in vitro growth-inhibitory activities against Saprolegnia strains, displaying greater anti-oomycete potency than the standard drugs used in the assay, namely fluconazole and bronopol. In contrast, a dramatic loss of activity was observed for O-alkylated derivatives 2, 3, 6, and 7. These findings have highlighted the therapeutic potential of the natural compound 1 scaffold to be exploitable as a drug lead with specific activity against various Saprolegnia strains. View Full-Text
Keywords: 2′,4′-dihydroxychalcone; chalcones; oomycetes; Saprolegnia 2′,4′-dihydroxychalcone; chalcones; oomycetes; Saprolegnia
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Montenegro, I.; Muñoz, O.; Villena, J.; Werner, E.; Mellado, M.; Ramírez, I.; Caro, N.; Flores, S.; Madrid, A. Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis. Molecules 2018, 23, 1377.

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