Synthesis and Evaluation of Novel Oxyalkylated Derivatives of 2',4'-Dihydroxychalcone As Anti-Oomycete Agents Against Bronopol Resistant Strains of Saprolegnia Sp

Overview

Journal Int J Mol Sci

Publisher MDPI

Specialties Biochemistry
Chemistry
Molecular Biology

Date 2016 Aug 25

PMID 27556457

Citations 10

Authors

Susana Flores

Ivan Montenegro

Joan Villena

Mauricio Cuellar

Enrique Werner

Patricio Godoy

Alejandro Madrid

Affiliations

Soon will be listed here.

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.

Citing Articles

Structure-Activity Relationship of Natural Dihydrochalcones and Chalcones, and Their Respective Oxyalkylated Derivatives as Anti- Agents.

Madrid A, Munoz E, Silva V, Martinez M, Flores S, Valdes F Plants (Basel). 2024; 13(14).

PMID: 39065502 PMC: 11281103. DOI: 10.3390/plants13141976.

Chemical Analysis and Bioactivity of Essential Oil of and Safrole Derivatives against Oomycete Fish Pathogens.

Madrid A, Morales A, Saffirio V, Cuellar M, Werner E, Said B Molecules. 2021; 26(21).

PMID: 34770960 PMC: 8588113. DOI: 10.3390/molecules26216551.

Identification of Growth Inhibitors of the Fish Pathogen Using Subtractive Proteomics, Computational Modeling, and Biochemical Validation.

Kumar S, Mandal R, Bulone V, Srivastava V Front Microbiol. 2020; 11:571093.

PMID: 33178154 PMC: 7596660. DOI: 10.3389/fmicb.2020.571093.

Sonochemical Synthesis of 2'-Hydroxy-Chalcone Derivatives with Potential Anti-Oomycete Activity.

Lopez G, Mellado M, Werner E, Said B, Godoy P, Caro N Antibiotics (Basel). 2020; 9(9).

PMID: 32899705 PMC: 7560025. DOI: 10.3390/antibiotics9090576.

Synthesis and Anti- Activity of New 2',4'-Dihydroxydihydrochalcone Derivatives.

Werner E, Montenegro I, Said B, Godoy P, Besoain X, Caro N Antibiotics (Basel). 2020; 9(6).

PMID: 32532060 PMC: 7344530. DOI: 10.3390/antibiotics9060317.

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