Title :

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

Author(s) :

García, Ainhoa [Auteur]
Universitat de València = University of Valencia [UV]
Vila, Laura [Auteur]
Universitat de València = University of Valencia [UV]
Marín, Paloma [Auteur]
Universitat de València = University of Valencia [UV]
Bernabeu, Álvaro [Auteur]
Universitat de València = University of Valencia [UV]
Villarroel-Vicente, Carlos [Auteur]
Universitat de València = University of Valencia [UV]
Hennuyer, Nathalie [Auteur]
Récepteurs Nucléaires, Maladies Métaboliques et Cardiovasculaires - U 1011 [RNMCD]
Staels, Bart [Auteur]
Récepteurs Nucléaires, Maladies Métaboliques et Cardiovasculaires - U 1011 [RNMCD]
Franck, Xavier [Auteur]
Chimie Organique et Bioorganique : Réactivité et Analyse [COBRA]
Figadère, Bruno [Auteur]
Biomolécules : Conception, Isolement, Synthèse [BioCIS]
Cabedo, Nuria [Auteur]
Universitat de València = University of Valencia [UV]
Cortes, Diego [Auteur]
Universitat de València = University of Valencia [UV]

Journal title :

ACS Medicinal Chemistry Letters

Publisher :

American Chemical Society

Publication date :

2021-10-06

ISSN :

1948-5875

English keyword(s) :

Prenylated benzopyrans
Horner-Wadsworth-Emmons reaction
PPARα/γ activity

HAL domain(s) :

Chimie/Chimie organique

English abstract : [en]

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 ...
Show more >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.Show less >

Language :

Anglais

Peer reviewed article :

Oui

Audience :

Internationale

Popular science :

Non

ANR Project :

EGID Diabetes Pole

Collections :

• Récepteurs nucléaires, Maladies Cardiovasculaires et Diabète (RNMCD) - U1011

Source :

Harvested from HAL