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Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates.

ABSTRACT: A library of embelin derivatives has been synthesized through a multicomponent reaction 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 multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including one important multiresistant Staphylococcus aureus clinical isolate. It was found how the conjugation of diverse privileged substructure with embelin led to adducts having enhanced antibacterial activities.

SUBMITTER: Martin-Acosta P

PROVIDER: S-EPMC7397138 | biostudies-literature | 2020 Jul

REPOSITORIES: biostudies-literature

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Efficient Multicomponent Synthesis of Diverse Antibacterial Embelin-Privileged Structure Conjugates.

Martín-Acosta Pedro P Peña Rosalyn R Feresin Gabriela G Tapia Alejandro A Lorenzo-Castrillejo Isabel I Machín Félix F Amesty Ángel Á Estévez-Braun Ana A

Molecules (Basel, Switzerland) 20200720 14

A library of embelin derivatives has been synthesized through a multicomponent reaction 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 multicomponent reaction implies Knoevenagel condensation, Michael addition, intramolecular cyclization and dehydration. Many of the synthesized compounds were active and selective against Gram-positive bacteria, including ...[more]

PMID: 32698422

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