Synthesis of 2-Prenylated Alkoxylated Benzopyrans by Horner-Wadsworth-Emmons olefination with PPARα/γ Agonist Activity
Résumé
We have synthesized series of 2-prenylated benzopyrans as analogs of the natural polycerasoidol, a dual PPARα/γ agonist with anti-inflammatory effect. The prenylated side chain consists of five-or nine-carbons with an α-alkoxy-α,β-unsaturated ester moiety. Prenylation was introduced via Grignard reaction, followed by Johnson-Claisen rearrangement, and the α-alkoxy-α,βunsaturated ester moiety by the Horner-Wadsworth-Emmons reaction. Synthetic derivatives showed high efficacy to activate both hPPARα and hPPARγ as dual PPARα/γ agonists. These prenylated benzopyrans emerge as lead compounds potentially useful for preventing cardiometabolic diseases.
Domaines
Chimie organiqueOrigine | Fichiers produits par l'(les) auteur(s) |
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