Complexos de cobre (II) de bases de Schiff prolínicas aplicados como inibidores e miméticos funcionais da enzima Urease e à formação de 1,2,3-triazóis 1,4-dissubstituídos

Abstract

In this work five Schiff base-type ligands derived from a series of reaction steps were synthesized starting from the amino acid L-proline, in which four of them are novel and were completely characterized by 1H, 13C, HSQC and HMBC 13C – 1H NMR techniques. Five new Cu (II) complexes were synthesized from the coordination of CuCl2 with the Schiff base ligands derived from the amino acid L-proline. These complexes were characterized by mass spectrometry, elemental analysis, conductivity, electron spin resonance, ultraviolet and visible infrared spectroscopy and electrochemical techniques. Based on the techniques discussed, it was possible to verify the tridentate coordination mode of the ligands in the form of phenolate as well as the assumption of only one chloride ion in the coordination sphere. The CuIIL2 complex was initially applied as a urease inhibitor derived from Canavalia ensiformis using the Berthelot method for detecting ammonia formed. It was observed that the complex inhibits urease in the millimolar range, however, the complexes themselves proved to be effective for ammonia formation through urea. The kinetic behavior of these complexes proved to bedependent on the organic solvent, acetonitrile or methanol. Finally, we explored the copper (I) azide - alkyne catalyzed reaction for the production of 1,4-disubstituted 1,2,3-triazoles starting from 1-azido-4-nitrobenzene by modifying terminal alkynes such as phenylacetylene, hex-1-yn and pent-4-yn-1-ol. The complexes were capable of producing the required triazoles in yields of up to 72%.