Synthesis by Click Reactions and Antiplasmodial Activity of Lupeol 1,2,3-Triazole Derivatives

• Autor(a) principal: Borgati,Tatiane F.
• Data de Publicação: 2017
• Outros Autores: Pereira,Guilherme R., Brandão,Geraldo C., Santos,Juliana O., Fernandes,Dayane Aparecida M., Paula,Renata C. de, Nascimento,Maria Fernanda A. do, Soares,Luciana F., Lopes,Júlio César D., Souza Filho,José D. de, Oliveira,Alaíde B. de
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Journal of the Brazilian Chemical Society (Online)
• Texto Completo: http://old.scielo.br/scielo.php?script=sci_arttext&pid=S0103-50532017001001850
• topic: lupeol; terpenoids; 1,2,3-triazole; click chemistry; antiplasmodial activity

Lupeol, a triterpene frequently found in Asteraceae plant species, showed moderate to low activity in different strains of Plasmodium falciparum, the most virulent malaria etiological agents. In this work, lupeol was isolated from Parahancornia fasciculata, a plant that is used to treat malaria in the Amazonia region. In the search of more activity lupeol derivatives, five new 1,2,3-triazole hybrid molecules were synthetized by copper-catalyzed azide-alkyne cycloaddition. The antiplasmodial activity of the semi-synthetic compounds were evaluated by the lactate dehydrogenase assay; the lupeol propargyl ether was the only one to disclosing increased activity (half maximal inhibitory concentration-IC50-62.0 ± 1.92 µmol L-1) in relation to lupeol (IC50 117.00 µmol L-1). Therefore, this work revealed a new class of interesting lupeol derivatives that can be obtained by linking electron donors to the hydroxy group at C-3.