Portal de Periódicos da CAPES

Efficient synthesis and antioxidant activity of novel N-propargyl tetrahydroquinoline derivatives through the cationic Povarov reaction

2019; Elsevier BV; Volume: 5; Issue: 8 Linguagem: Inglês

10.1016/j.heliyon.2019.e02174

2405-8440

Yeray A. Rodríguez‐Núñez, Maximiliano Norambuena, Arnold R. Romero Bohórquez, Alejandro Morales‐Bayuelo, Margarita Gutiérrez,

Synthesis and biological activity

New N-propargyl tetrahydroquinolines 6a-g have been synthesized efficiently through the cationic Povarov reaction (a domino Mannich/Friedel-Crafts reaction), catalyzed by Indium (III) chloride (InCl3), from the corresponding N-propargylanilines preformed, formaldehyde and N-vinylformamide, with good to moderate yields. All tetrahydroquinoline derivatives obtained were evaluated in vitro as free radical scavengers. Results showed that compound 6c presents a potent antioxidant effect compared with ascorbic acid, used as a reference compound. ADME predictions also revealed favorable pharmacokinetic parameters for the synthesized compounds, which warrant their suitability as potentials antioxidant. Additionally, a theoretical study using Molecular Quantum Similarity and reactivity indices were developed to discriminate different reactive sites in the new molecules in which the oxidative process occurs.