Synthesis and trypanocidal activity of ent-kaurane glycosides.

• Autor(a) principal: Batista, Ronan
• Data de Publicação: 2007
• Outros Autores: Humberto, Jorge Luiz, Chiari, Egler, Oliveira, Alaíde Braga de
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da UFOP
• dARK ID: ark:/61566/00130000056hk
• Texto Completo: http://www.repositorio.ufop.br/handle/123456789/5089; https://doi.org/10.1016/j.bmc.2006.09.048
• topic: Kaurenoic acid; Koenigs–Knorr reaction; Trypanosoma cruzi

Novel ent-kaurane glucosides were synthezised by a Koenigs–Knorr reaction between C17 and C19 alcohols derived from kaurenoic acid and 2,3,4,6-tetra-O-acetyl-glucopyranosyl bromide, followed by the hydrolysis of the acetates. Main products were assayed in vitro and in vivo against blood trypomastigote forms of Trypanosoma cruzi, the aetiological agent of Chagas’ disease (American trypanosomiasis). The results allowed to establish structure–activity relationships among these derivatives, as well as pointed out the C19-methylester-C17-O-glucoside as a potential trypanocidal agent, whose trypanocidal profile was shown to be comparable to those of gentian violet and benznidazole.