title: Synthesis and Evaluation of Novel Oxyalkylated Derivatives of 2',4'-Dihydroxychalcone as Anti-Oomycete Agents against Bronopol Resistant Strains of Saprolegnia sp.
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.
authors.affiliation: Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile. s.flore.gonzalez@gmail.com.
authors.forename: Susana
authors.initials: S
authors.lastname: Flores
authors.affiliation: Escuela de Obstetricia y Puericultura, Facultad de medicina, Campus de la Salud, Universidad de Valparaíso, Angamos 655, Reñaca, Viña del Mar 2520000, Chile. ivan.montenegro@uv.cl.
authors.forename: Iván
authors.initials: I
authors.lastname: Montenegro
authors.affiliation: Centro de Investigaciones Biomédicas (CIB), Escuela de Medicina, Universidad de Valparaíso, Av. Hontaneda N° 2664, Valparaíso 2340000, Chile. juan.villena@uv.cl.
authors.forename: Joan
authors.initials: J
authors.lastname: Villena
authors.affiliation: Facultad de Farmacia, Universidad de Valparaíso, Av. Gran Bretaña N° 1093, Valparaíso 2340000, Chile. mauricio.cuellar@uv.cl.
authors.forename: Mauricio
authors.initials: M
authors.lastname: Cuellar
authors.affiliation: Departamento De Ciencias Básicas, Campus Fernando May Universidad del Biobío, Avda. Andrés Bello s/n casilla 447, Chillán 3780000, Chile. ewerner@ubiobio.cl.
authors.forename: Enrique
authors.initials: E
authors.lastname: Werner
authors.affiliation: Instituto de Microbiología Clínica, Facultad de Medicina, Universidad Austral de Chile, Los Laureles s/n, Isla Teja, Valdivia 5090000, Chile. patricio.godoy@uach.cl.
authors.forename: Patricio
authors.initials: P
authors.lastname: Godoy
authors.affiliation: Departamento de Química, Facultad de Ciencias Naturales y Exactas, Universidad de Playa Ancha, Avda. Leopoldo Carvallo 270, Playa Ancha, Valparaíso 2340000, Chile. alejandro.madrid@upla.cl.
authors.forename: Alejandro
authors.initials: A
authors.lastname: Madrid
mesh_terms: D000818:Animals; D000935:Antifungal Agents / Q000494:pharmacology; D047188:Chalcones / Q000494:pharmacology*; D008826:Microbial Sensitivity Tests; D011409:Propylene Glycols / Q000494:pharmacology; D044762:Saprolegnia / Q000187:drug effects*
chemical_list: D000935:Antifungal Agents; D047188:Chalcones; D011409:Propylene Glycols; C059354:2',4'-dihydroxychalcone; C006827:bronopol
keywords: Saprolegnia australis; Saprolegnia parasitica; fish pathogen; oxyalkylchalcones