A Mild and Versatile Friedel-Crafts Methodology for the Diversity-Oriented Synthesis of Redox-Active 3-Benzoylmenadiones with Tuneable Redox Potentials.
Fiche publication
Date publication
novembre 2019
Journal
Chemistry (Weinheim an der Bergstrasse, Germany)
Auteurs
Membres identifiés du Cancéropôle Est :
Dr DAVIOUD-CHARVET Elisabeth , Dr ELHABIRI Mourad
Tous les auteurs :
Cotos L, Donzel M, Elhabiri M, Davioud-Charvet E
Lien Pubmed
Résumé
A series of highly diversified 3-aroylmenadiones was prepared by a new Friedel-Crafts acylation variant/oxidative demethylation strategy. A Mild and versatile acylation was performed between 1,4-dimethoxy-2-methylnaphthalene and various activated/deactivated benzoic and heteroaromatic carboxylic acids, in the presence of mixed trifluoroacetic anhydride and triflic acid, at room temperature and air moisture. The 1,4-dimethoxy-2-methylnaphthalene-derived benzophenones were isolated in high yield, and submitted to oxidative demethylation with cerium ammonium nitrate to produce 3-benzoylmenadiones. All 1,4- naphthoquinone derivatives were investigated as redox-active electrophores by cyclic voltammetry. The electrochemical data recorded on 3-acylated menadiones are characterized by a second redox process whose potentials cover a wide range of values (500 mV). These data emphasize the ability of the reached structural diversity at the 3-aroyl chain of these electrophores to fine-tune their corresponding redox potentials. These properties are of significant importance in the context of antimalarial drug development and understanding of the mechanism of bioactivation/action.
Mots clés
Friedel-Crafts, acylation, acyltrifluoroacetate, benzoyl, electrochemistry
Référence
Chemistry. 2019 Nov 20;: