Synthesis of Benzofuran-2-One Derivatives and Evaluation of Their Antioxidant Capacity by Comparing DPPH Assay and Cyclic Voltammetry

Molecules

M. Antonietta Loreto¹  Marta Feroci²  Paolo Rosa³  Tecla Gasperi⁴  Martina Miceli⁴  Daniela Tofani⁴  Elia Roma⁴ 

[1] Dipartimento di Chimica, Sapienza Università di Roma, p.le A. Moro 5, I-00185 Roma, Italy;Dipartimento di Scienze di Base e Applicate per l’Ingegneria, Sapienza Università di Roma, via Castro Laurenziano 7, I-00161 Roma, Italy;Dipartimento di Scienze e Biotecnologie Medico-Chirurgiche, Sapienza Università di Roma—Polo Pontino, Corso della Repubblica 79, 04100 Latina, Italy;Dipartimento di Scienze, Sezione di Nanoscienze e Nanotecnologie, Università degli Studi di Roma Tre, via della Vasca Navale 79, I-00146 Roma, Italy;

关键词: antioxidant activity;    cyclic voltammetry;    DPPH;    domino reaction;    benzofuran-2-ones;   

DOI  :  10.3390/molecules23040710

来源: DOAJ

【 摘 要 】

The present work aimed to synthesise promising antioxidant compounds as a valuable alternative to the currently expensive and easily degradable molecules that are employed as stabilizers in industrial preparation. Taking into account our experience concerning domino Friedel-Crafts/lactonization reactions, we successfully improved and extended the previously reported methodology toward the synthesis of 3,3-disubstituted-3H-benzofuran-2-one derivatives 9–20 starting from polyphenols 1–6 as substrates and either diethylketomalonate (7) or 3,3,3-trifluoromethyl pyruvate (8) as electrophilic counterpart. The antioxidant capacity of the most stable compounds (9–11 and 15–20) was evaluated by both DPPH assay and Cyclic Voltammetry analyses performed in alcoholic media (methanol) as well as in aprotic solvent (acetonitrile). By comparing the recorded experimental data, a remarkable activity can be attributed to few of the tested lactones.

【 授权许可】

Unknown