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Int. J. Mol. Sci. 2016, 17(8), 1366; doi:10.3390/ijms17081366

Synthesis and Evaluation of Novel Oxyalkylated Derivatives of 2′,4′-Dihydroxychalcone as Anti-Oomycete Agents against Bronopol Resistant Strains of Saprolegnia sp.

1
Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile
2
Escuela de Obstetricia y Puericultura, Facultad de medicina, Campus de la Salud, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, Chile
3
Centro de Investigaciones Biomédicas (CIB), Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso 2340000, Chile
4
Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso 2340000, Chile
5
Departamento De Ciencias Básicas, Campus Fernando May Universidad del Biobío, Avda. Andrés Bello s/n casilla 447, Chillán 3780000, Chile
6
Instituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Los Laureles s/n, Isla Teja, Valdivia 5090000, Chile
*
Author to whom correspondence should be addressed.
Academic Editor: Yujiro Hayashi
Received: 21 July 2016 / Revised: 5 August 2016 / Accepted: 16 August 2016 / Published: 22 August 2016
(This article belongs to the Section Green Chemistry)
View Full-Text   |   Download PDF [899 KB, uploaded 22 August 2016]   |  

Abstract

A series of novel oxyalkylchalcones substituted with alkyl groups were designed and synthesized, and the antioomycete activity of the series was evaluated in vitro against Saprolegnia strains. All tested O-alkylchalcones were synthesized by means of nucleophilic substitution from the natural compound 2′,4′-dihydroxychalcone (1) and the respective alkyl bromide. The natural chalcone (1) and 10 synthetic oxyalkylchalcones (211) were tested against Saprolegnia parasitica and Saprolegnia australis. Among synthetic analogs, 2-hydroxy,4-farnesyloxychalcone (11) showed the most potent activity against Saprolegnia sp., with MIC and MOC values of 125 µg/mL (similar to bronopol at 150 µg/mL) and 175 µg/mL, respectively; however, 2′,4′-dihydroxychalcone (1) was the strongest and most active molecule, with MIC and MOC values of 6.25 µg/mL and 12.5 µg/mL. View Full-Text
Keywords: oxyalkylchalcones; fish pathogen; Saprolegnia parasitica; Saprolegnia australis oxyalkylchalcones; fish pathogen; Saprolegnia parasitica; Saprolegnia australis
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MDPI and ACS Style

Flores, S.; Montenegro, I.; Villena, J.; Cuellar, M.; Werner, E.; Godoy, P.; Madrid, A. Synthesis and Evaluation of Novel Oxyalkylated Derivatives of 2′,4′-Dihydroxychalcone as Anti-Oomycete Agents against Bronopol Resistant Strains of Saprolegnia sp.. Int. J. Mol. Sci. 2016, 17, 1366.

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