Síntese, Caracterização, Estudo Conformacional e Biológico das 2’-Nitro e 3’-Nitro-4-Hidroxi-3-Metoxichalconas

Abstract

This study presents a conformational analysis of the isomers 2'-nitro-4-hydroxy-3- methoxychalcone (o-CHAL) and 3'-nitro-4-hydroxy-3-methoxychalcone (m-CHAL). Using theoretical calculations, the conformers present in conformational equilibrium of compounds were obtained, since the s-cis conformations represent the most stable forms for the two isomers performed. The analyzes of the natural bond orbitals (NBO) carried out density functional theory (DFT), in combination with M06-2X method and basis set 6-311 ++ G (2d, dp), revealed greater electronic delocation in the s-cis conformers. However, the stability of the s-trans conformers was influenced by the position of the nitro group in ring A of chalcones. The antioxidant potential was evaluated by DPPH method and Ferrous ion chelating activity, the chalcone o-CHAL presented promising results, probably will be the focus for further evaluations in the future.