Synthesis of xylitan derivatives and preliminary evaluation of in vitro trypanocidal activity.

• Autor(a) principal: Elias, Paula Regina
• Data de Publicação: 2016
• Outros Autores: Coelho, Gleicekelly Silva, Xavier, Viviane Flores, Sales Júnior, Policarpo Ademar, Romanha, Alvaro José, Murta, Silvane Maria Fonseca, Carneiro, Claudia Martins, Camilo, Nilton Soares, Hilário, Flaviane Francisco, Taylor, Jason Guy
• Tipo de documento: Artigo
• Idioma: eng
• Título da fonte: Repositório Institucional da UFOP
• Texto Completo: http://www.repositorio.ufop.br/handle/123456789/11181; https://doi.org/10.3390/molecules21101342
• topic: Xylitol; Anhydropentitol; Trypomastigote; Chagas disease; Amastigote

A series of novel xylitan derivatives derived from xylitol were synthesized using operationally simple procedures. A xylitan acetonide was the key intermediate used to prepare benzoate, arylsulfonate esters and 1,2,3-triazole derivatives of xylitan. These compounds were evaluated for their in vitro anti-Trypanosoma cruzi activity against trypomastigote and amastigote forms of the parasite in T. cruzi-infected cell lineages. Benznidazole was used as positive control against T. cruzi and cytotoxicity was determined in mammalian L929 cells. The arylsulfonate xylitan derivative bearing a nitro group displayed the best activity of all the compounds tested, and was slightly more potent than the reference drug benznidazole. The importance of the isopropylidene ketal moiety was established and the greater lipophilicity of these compounds suggests enhancement in cell penetration.