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

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...

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Autores principales: Elias, Paula Regina, Coelho, Gleicekelly Silva, Xavier, Viviane Flores, Sales Junior, Policarpo Ademar, Romanha, Alvaro José, Murta, Silvane Maria Fonseca, Carneiro, Claudia Martins, Camilo, Nilton Soares, Hilário, Flaviane Francisco, Taylor, Jason Guy
Formato: Online Artículo Texto
Lenguaje:English
Publicado: MDPI 2016
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273285/
https://www.ncbi.nlm.nih.gov/pubmed/27735872
http://dx.doi.org/10.3390/molecules21101342
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author Elias, Paula Regina
Coelho, Gleicekelly Silva
Xavier, Viviane Flores
Sales Junior, Policarpo Ademar
Romanha, Alvaro José
Murta, Silvane Maria Fonseca
Carneiro, Claudia Martins
Camilo, Nilton Soares
Hilário, Flaviane Francisco
Taylor, Jason Guy
author_facet Elias, Paula Regina
Coelho, Gleicekelly Silva
Xavier, Viviane Flores
Sales Junior, Policarpo Ademar
Romanha, Alvaro José
Murta, Silvane Maria Fonseca
Carneiro, Claudia Martins
Camilo, Nilton Soares
Hilário, Flaviane Francisco
Taylor, Jason Guy
author_sort Elias, Paula Regina
collection PubMed
description 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.
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spelling pubmed-62732852018-12-28 Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity Elias, Paula Regina Coelho, Gleicekelly Silva Xavier, Viviane Flores Sales Junior, Policarpo Ademar Romanha, Alvaro José Murta, Silvane Maria Fonseca Carneiro, Claudia Martins Camilo, Nilton Soares Hilário, Flaviane Francisco Taylor, Jason Guy Molecules Article 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. MDPI 2016-10-10 /pmc/articles/PMC6273285/ /pubmed/27735872 http://dx.doi.org/10.3390/molecules21101342 Text en © 2016 by the authors. Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC-BY) license (http://creativecommons.org/licenses/by/4.0/).
spellingShingle Article
Elias, Paula Regina
Coelho, Gleicekelly Silva
Xavier, Viviane Flores
Sales Junior, Policarpo Ademar
Romanha, Alvaro José
Murta, Silvane Maria Fonseca
Carneiro, Claudia Martins
Camilo, Nilton Soares
Hilário, Flaviane Francisco
Taylor, Jason Guy
Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_full Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_fullStr Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_full_unstemmed Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_short Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity
title_sort synthesis of xylitan derivatives and preliminary evaluation of in vitro trypanocidal activity
topic Article
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC6273285/
https://www.ncbi.nlm.nih.gov/pubmed/27735872
http://dx.doi.org/10.3390/molecules21101342
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