Synthesis of 2-Prenylated Alkoxylated Benzopyrans by Horner-Wadsworth-Emmons Olefination with PPARa/? Agonist Activity.

Fecha de publicación: 11/11/2021 Fecha Ahead of Print: 06/10/2021

Autores de INCLIVA

• 

  Laura Vila Dasí

  Autor

• Carlos Villarroel Vicente

  Autor

• 

  Nuria Cabedo Escrig

  Autor

• 

  Diego Cortes Martinez

  Autor

Participantes ajenos a INCLIVA

• Garcia, A
• Marin, P
• Bernabeu, A
• Hennuyer, N
• Staels, B
• Franck, X
• Figadere, B

Grupos y Plataformas de I+D+i

• Grupo de Investigación en Inflamación

  

  Leading Researcher

  Maria Jesus Sanz Ferrando

• Unidad de Cromatografía Líquida Analítica

  

  Responsable de Plataforma

  Nuria Cabedo Escrig

Abstract

We have synthesized series of 2-prenylated benzopyrans as analogues of the natural polycerasoidol, a dual PPARa/? agonist with anti-inflammatory effects. The prenylated side chain consists of five or nine carbons with an a-alkoxy-a,ß-unsaturated ester moiety. Prenylation was introduced via the Grignard reaction, followed by Johnson-Claisen rearrangement, and the a-alkoxy-a,ß-unsaturated ester moiety was introduced by the Horner-Wadsworth-Emmons reaction. Synthetic derivatives showed high efficacy to activate both hPPARa and hPPAR? as dual PPARa/? agonists. These prenylated benzopyrans emerge as lead compounds potentially useful for preventing cardiometabolic diseases.

© 2021 American Chemical Society.