Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates

MARTÍN-ACOSTA, PEDRO; PEÑA, ROSALYN; FERESIN, GABRIELA; TAPIA, ALEJANDRO; LORENZO-CASTRILLEJO, ISABEL; MACHÍN, FÉLIX; AMESTY, ÁNGEL; ESTÉVEZ-BRAUN, ANA

MOLECULES

MOLECULAR DIVERSITY PRESERVATION INTERNATIONAL-MDPI

Año: 2020 vol. 25

1420-3049

A library of embelin derivatives has been synthesized through a multicomponentreaction from embelin (1), aldehydes and privileged structures such as 4-hydroxycoumarin,4-hydroxy-2H-pyran-2-one and 2-naphthol, in the presence of InCl3 as catalyst. This multicomponentreaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization anddehydration. Many of the synthesized compounds were active and selective against Gram-positivebacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was foundhow the conjugation of diverse privileged substructure with embelin led to adducts having enhancedantibacterial activities.