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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...
Autores principales: | , , , , , , , , , |
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Formato: | Online Artículo Texto |
Lenguaje: | English |
Publicado: |
MDPI
2016
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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. |
format | Online Article Text |
id | pubmed-6273285 |
institution | National Center for Biotechnology Information |
language | English |
publishDate | 2016 |
publisher | MDPI |
record_format | MEDLINE/PubMed |
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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