Síntese e avaliação biológica de 1,2,3-triazóis-1,4-dissubstituídos derivados de benzocalcogenoanilinas e 2-aril-4-(azidometil)-1,3-calcogenazóis

Abstract

In the present work two new series of 1,2,3-triazoles-1,4-disubstituted 20-33 obtained by the reaction of 1,3-dipolar cycloaddition, Click-type, were synthesized between the alkaloids derived from benzocalcogenoanilines and the azides of 1,3-chalcogenazoles-2-substituted with the objective of joining three classes of interesting heterocyclic compounds and to explore the biological properties of these molecules in question. Compounds 17-19 were obtained from the bimolecular nucleophilic substitution reaction (SN2) in yields ranging from 55-90% and the alkynes 7, 8 and 26, 27 were also synthesized by SN2 reaction and demonstrated yields ranging from 30-55%. For the synthesis of 1,2,3-triazoles-1,4-disubstituted 25-33, the 1,3-dipolar cycloaddition reaction, which involves azides 17-19 and alkynes in the presence of copper catalyst (CuI) and a mixture of solvents t-BuOH/H2O to obtain the triazole 20-25, whereas for the synthesis of the triazoles 28-33 water was used as the solvent. Yields for the obtained compounds ranged from 75-98% and 72-98%, respectively. According to the tests of antimicrobial activity, a considerable number of compounds were active against the tested microorganisms. The compounds were evaluated for in vitro antimicrobial activity against Gram-positive and Gram-negative bacteria, as well as antifungal activity, with 25a-d compounds showing promising results both in terms of antimicrobial and antioxidant activity.