Rapid synthesis of triazole-modified resveratrol analogues via click chemistry

  • J Med Chem. 2006 Jan 26;49(2):467-70. doi: 10.1021/jm051118z.
Francesca Pagliai  1 ,  Tracey Pirali ,  Erika Del Grosso ,  Riccardo Di Brisco ,  Gian Cesare Tron ,  Giovanni Sorba ,  Armando A Genazzani
Affiliations
  • 1. Dipartimento di Scienze Chimiche, Alimentari, Farmaceutiche e Farmacologiche, Università degli Studi del Piemonte Orientale A. Avogadro, 28100 Novara, Italy.
PMID: 16420033 DOI: 10.1021/jm051118z
Abstract

Resveratrol is a phytoalexin able to display an array of biological activities. We decided to replace the double bond with a triazole ring using the archetypical click reaction: the Huisgen [3 + 2] cycloaddition. Seventy-two triazole derivatives were synthesized via a parallel combinatorial approach. Preliminary data suggest that this procedure can lead to the synthesis of compounds that display some, but not all, of resveratrol's actions with increased potency.