Síntese de bis-1,2,3-triazóis 1,4-dissubstituídos aromáticos simétricos via reação CuAAC com potencial atividade leishmanicida.

Abstract

The azide-alkaline cycloaddition reaction catalyzed by Cu (I) is a highly regioselectivity reaction since it forms only the 1,4-disubstituted 1,2,3-triazole and is an adaptation of the 1,3- Huisgen dipolar that forms both regioisomers. In addition, CuAAC is within the precepts of click chemistry, which makes it very accessible in several syntheses due to the possibility of obtaining highly complex molecules, in mild conditions, using solvents that are not aggressive to the environment and without the need for methods chromatographic for purification. Previously in the group, leishmanicidal tests were performed and it was observed that the symmetrical aromatic 1,4-disubstituted bis-1,2,3-triazoles showed considerable leishmanicidal activity, so a second generation of symmetrical aromatic bis-triazoles has been proposed since it is proven in the literature that triazoles have leishmanicidal activity in addition to others. This biological activity is justified mainly due to the planar shape of the triazolic ring that allows it to perform π-stacking interactions in addition to the possibility of hydrogen bonds. Thus, for the synthesis of the symmetrical 1,4-disubstituted aromatic bis-1,2,3-triazoles, organic azides were obtained first and some alkynes were of commercial origin while another was obtained through the Sonogashira cross-coupling reaction. An in silico study was also carried out to evaluate the potential leishmanicidal activity of the compounds and some presented promising results. During the research, a parallel work was also carried out that generated an article entitled "Use of biomass in undergraduate classes in experimental organic chemistry: Extraction of flavonoids from citrus peel residues"