Sonochemical synthesis of 2’‐hydroxy‐chalcone derivatives with potential anti‐oomycete activity

Génesis López, MARCO ANDRÉS MELLADO GARCÍA, Enrique Werner, Bastián Said, Patricio Godoy, Nelson Caro, XIMENA ALEJANDRA BESOAIN CANALES, Iván Montenegro, Alejandro Madrid

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Abstract

This work reports on the synthesis of eight new 2′‐hydroxy‐chalcones with potential anti-phytopathogenic applications in agroindustry, AMONG others, via Claisen–Schmidt condensation and ultrasound assisted reaction. Assays showed three chalcones with allyl moieties strongly inhibited growth of phytopathogenic oomycete Phytophthora infestans; moreover, compound 8a had a half maximal effective concentration (EC50) value (32.5 μg/mL) similar to that of metalaxyl (28.6 μg/mL). A software‐aided quantitative structure–activity relationship (QSAR) analysis of the whole series suggests that the structural features of these new chalcones—namely, the fluoride, hydroxyl, and amine groups over the carbon 3′ of the chalcone skeleton—increase anti‐oomycete activity.

Original languageEnglish
Article number576
Pages (from-to)1-12
Number of pages12
JournalAntibiotics
Volume9
Issue number9
DOIs
StatePublished - Sep 2020
Externally publishedYes

Keywords

  • Chalcone
  • Phytophthora infestans
  • Ultrasound

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