Síntese de triazóis com potencial atividade biológica através de reações Click

Abstract

This dissertation's Graduate Chemistry course is an approach of the synthesis of substances with potential biological activity, using as key step the reaction of CuAAC - azide-alkyne cycloaddition employing copper as a catalyst for reaction - following the precepts of Click Chemistry, introduced by K. Barry Sharpless in 2001. The work was divided into two main parts: the first was the synthesis of substances with similar potential antileishmania activity that were presented in the work of Silva and coworkers in 2010, employing CuAAC reactions, but presenting innovation as the insertion of the triazole unit. This synthetic route was the precursor of dimethyl 3-oxo-glutarate in synthetic routes A and B. Synthetic routes (C and D) were also developed, in addition to the reaction of transketalization and complementary reactions, culminating in the synthesis of 22 substances. The second part, in turn, was to synthesize a family of chiral triazoles from chiral azides by kinetic resolution and terminal alkynes, also using the CuAAC reaction, being possible to obtain a variety of chiral triazoles (7 in total) with potential fungicidal activity. Most of the triazoles synthesized in this dissertation were submitted to biological tests at the Federal University of Lavras (UFLA) in Minas Gerais. However, only triazole 78 was active for both breeds 65 and 89 of the Colletotrichum lindemunthianum agricultural fungus and in the subsequent test to verify fungicidal activity, the value found in the MIC was 250 μg / mL.The results, discussions about these experiments, beyond any characterization of the products obtained from analytical techniques such as 1H and 13C NMR, FTIR, melting point and biolocical tests will be presented in this paper.