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. 2016 Aug 22;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

Susana Flores  1 , Iván Montenegro  2 , Joan Villena  3 , Mauricio Cuellar  4 , Enrique Werner  5 , Patricio Godoy  6 , Alejandro Madrid  7
Affiliations

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

Susana Flores et al. Int J Mol Sci. .

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 (2-11) 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.

Keywords: Saprolegnia australis; Saprolegnia parasitica; fish pathogen; oxyalkylchalcones.

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Figures

Scheme 1
Scheme 1
General procedure for the synthesis of O-alkylated chalcones.
Figure 1
Figure 1
Most important correlations 2D 1H–13C HMBC, compound 4.
Figure 2
Figure 2
Most important correlations 2D 1H–13C HMBC, compound 5.
Figure 3
Figure 3
Most important correlations 2D 1H–13C HMBC, compounds 7 and 8.
See this image and copyright information in PMC

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