Structure-activity relationship of dialkoxychalcones to combat fish pathogen saprolegnia Australis

Iván Montenegro, Ociel Mu oz, Joan Villena, Enrique Werner, MARCO ANDRÉS MELLADO GARCÍA, Ingrid Ramírez, Nelson Caro, Susana Flores, Alejandro Madrid

Research output: Contribution to journalArticlepeer-review

6 Scopus citations

Abstract

To investigate the anti-Saprolegnia activities of chalconic compounds, nine dialkoxychalcones 2–10, 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 4–10 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.

Original languageEnglish
Article number1377
JournalMolecules
Volume23
Issue number6
DOIs
StatePublished - 1 Jan 2018

Keywords

  • 2'4'-dihydroxychalcone
  • Chalcones
  • Oomycetes
  • Saprolegnia

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