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Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity

Authors :
Paula Regina Elias
Gleicekelly Silva Coelho
Viviane Flores Xavier
Policarpo Ademar Sales Junior
Alvaro José Romanha
Silvane Maria Fonseca Murta
Claudia Martins Carneiro
Nilton Soares Camilo
Flaviane Francisco Hilário
Jason Guy Taylor
Source :
Molecules, Vol 21, Iss 10, p 1342 (2016)
Publication Year :
2016
Publisher :
MDPI AG, 2016.

Abstract

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.

Details

Language :
English
ISSN :
14203049
Volume :
21
Issue :
10
Database :
Directory of Open Access Journals
Journal :
Molecules
Publication Type :
Academic Journal
Accession number :
edsdoj.f3c4f9968b334497ab80a6da4c5440bf
Document Type :
article
Full Text :
https://doi.org/10.3390/molecules21101342