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Synthesis of 2-Prenylated Alkoxylated Benzopyrans by Horner-Wadsworth-Emmons olefination with PPARα/γ Agonist Activity

Abstract : 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.
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https://hal-normandie-univ.archives-ouvertes.fr/hal-03373981
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Submitted on : Monday, October 11, 2021 - 5:51:23 PM
Last modification on : Wednesday, December 1, 2021 - 2:42:25 PM

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Ainhoa García, Laura Vila, Paloma Marín, Álvaro Bernabeu, Carlos Villarroel-Vicente, et al.. Synthesis of 2-Prenylated Alkoxylated Benzopyrans by Horner-Wadsworth-Emmons olefination with PPARα/γ Agonist Activity. ACS Medicinal Chemistry Letters, American Chemical Society, 2021, ⟨10.1021/acsmedchemlett.1c00400⟩. ⟨hal-03373981⟩

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