Synthesis of functionalized heterocycles by palladium-catalyzed reactions, metathesis and acid mediated cycloisomerization
Keywords:
Sonogashira, Suzuki, metathesis, cycloisomerization, heterocycleAbstract
Introduction: Nitrogenous heterocyclic compounds, specifically those derived from pyridine, are widely used in different branches of science, with special interest in the field of materials science and the pharmaceutical industry, where they have reached their maximum application due to their antimalarial properties. muscle relaxant, cardiac depressant and anticancer. The objectives of this work were to synthesize new pyridine and quinoline derivatives of interest in materials science and in the pharmaceutical industry through palladium-catalyzed reactions, metathesis and acid-mediated cycloisomerization, to isolate, purify and structurally characterize these compounds, as well as to evaluate the selective inhibitory activities against ecto-5'-nucleotidase and the optical properties of the selected promising compounds.
Methods: They were established novel methodologies for the synthesis, using selective cross-coupling reactions of Suzuki, Sonogashira and Buchwald-Hartwig amination reactions, carbonyl-alkyne metathesis and acid-mediated cycloisomerization. These compounds were purified and characterized using chromatographic, spectroscopic, and spectrometric techniques. The optical properties were evaluated by ultraviolet-visible and fluorescence spectroscopy while the selective inhibitory activity against ecto-5'-nucleotidase was determined by capillary electrophoresis.
Results: The results of this work allowed to obtain 231 new compounds with good yields. It was evaluated in vitro the selective inhibitory activity against ecto-5'-nucleotidase of 25 aryl derivatives of quinoline, with good results, demonstrating its potential as an anticancer agent. In addition, the alkynylated pyridines derivatives obtained showed excellent optical properties with quantum yields that reached 55 % while 6-azaindoles reached 44 %. Conclusions: The palladium-catalyzed reactions, metathesis and acid-mediated cycloisomerization used, allowed the synthesis of new functionalized heterocyclic compounds derived from pyridine and quinoline with good yields. They were isolated, purified and structurally characterized all the compounds and they were determined the selective inhibitory activity against ecto-5'-nucleotidase and the optical properties of the selected compounds with excellent results.
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