Cargando…

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

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-alkyla...

Descripción completa

Detalles Bibliográficos
Autores principales: Montenegro, Iván, Muñoz, Ociel, Villena, Joan, Werner, Enrique, Mellado, Marco, Ramírez, Ingrid, Caro, Nelson, Flores, Susana, Madrid, Alejandro
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2018
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100462/
https://www.ncbi.nlm.nih.gov/pubmed/29875340
http://dx.doi.org/10.3390/molecules23061377
_version_ 1783348879698165760
author Montenegro, Iván
Muñoz, Ociel
Villena, Joan
Werner, Enrique
Mellado, Marco
Ramírez, Ingrid
Caro, Nelson
Flores, Susana
Madrid, Alejandro
author_facet Montenegro, Iván
Muñoz, Ociel
Villena, Joan
Werner, Enrique
Mellado, Marco
Ramírez, Ingrid
Caro, Nelson
Flores, Susana
Madrid, Alejandro
author_sort Montenegro, Iván
collection PubMed
description 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.
format Online
Article
Text
id pubmed-6100462
institution National Center for Biotechnology Information
language English
publishDate 2018
publisher MDPI
record_format MEDLINE/PubMed
spelling pubmed-61004622018-11-13 Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis Montenegro, Iván Muñoz, Ociel Villena, Joan Werner, Enrique Mellado, Marco Ramírez, Ingrid Caro, Nelson Flores, Susana Madrid, Alejandro Molecules Article 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. MDPI 2018-06-07 /pmc/articles/PMC6100462/ /pubmed/29875340 http://dx.doi.org/10.3390/molecules23061377 Text en © 2018 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Montenegro, Iván
Muñoz, Ociel
Villena, Joan
Werner, Enrique
Mellado, Marco
Ramírez, Ingrid
Caro, Nelson
Flores, Susana
Madrid, Alejandro
Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis
title Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis
title_full Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis
title_fullStr Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis
title_full_unstemmed Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis
title_short Structure-Activity Relationship of Dialkoxychalcones to Combat Fish Pathogen Saprolegnia australis
title_sort structure-activity relationship of dialkoxychalcones to combat fish pathogen saprolegnia australis
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6100462/
https://www.ncbi.nlm.nih.gov/pubmed/29875340
http://dx.doi.org/10.3390/molecules23061377
work_keys_str_mv AT montenegroivan structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT munozociel structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT villenajoan structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT wernerenrique structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT melladomarco structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT ramirezingrid structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT caronelson structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT floressusana structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis
AT madridalejandro structureactivityrelationshipofdialkoxychalconestocombatfishpathogensaprolegniaaustralis