Síntese de novos heterociclos híbridos 1,2,3- triazóis-furânicos e estudo da atividade anti- Trypanosoma cruzi

Abstract

The presente work consisted of the synthesis and evaluation of 17 previously unknown 1,2,3-triazoles attached to a furanic group and subsequent analysis of the inhibitory capacity of the molecules against T.cruzi agents. To obtain the proposed products the synthetic route initially involved the terminal alkyne derived from the furfural and the formation of an azide’s family derivative from aromatic anilines and the D-ribose. The obtainment process of the aromatic azides started with the addition of a sodium nitrite solution in acidic medium to form de diazonium salt, followed by the addition of a sodium azide solution to obtain the azide group. The azide derived from the D-ribose was synthesized in three steps, the first was the protection of the free hydroxyls groups of the D-ribose, subsequently, a tosilation reaction was carried out with the para-toluenesulfonyl chloride in order to improve the leavind group to obtain the azide derivative in the third step. The formation of the hybrid heterocycle 1,2,3-triazoles-furan was carried out by the copper-catalyzed 1,3-dipolar cycloaddition reaction from the aromatic azide and from the terminal alkyne. The new derivatives were obtained in yelds between 67-93%. The structural elucidation of the synthesized compounds was performed by infrared spectroscopy, 1H and 13C nuclear magnetic resonance spectroscopy and high-resolution mass spectrometry. The final products were sent for evaluation of their inhibitory activity again T. cruzi in colaboration with de Cell Biology Laboratory at Oswaldo Cruz Institute, Fiocruz, in the care of Drª Nazaré Soeiro and the technician Roberson Girão.