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Molecules 2016, 21(10), 1342; doi:10.3390/molecules21101342

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

1
Chemistry Department, ICEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto, MG, Brazil
2
Centro de Pesquisas René Rachou, A Fundação Oswaldo Cruz/FIOCRUZ, 30190-002 Belo Horizonte, MG, Brazil
3
Immunopathology Laboratory, NUPEB, Federal University of Ouro Preto, Campus Universitário Morro do Cruzeiro, 35400-000 Ouro Preto-MG, Brazil
4
Instituto de Química, Universidade Estadual de Campinas, C.P. 6154, CEP. 13084-971 Campinas, SP, Brazil
*
Author to whom correspondence should be addressed.
Academic Editor: Maria Emília de Sousa
Received: 4 September 2016 / Revised: 26 September 2016 / Accepted: 30 September 2016 / Published: 10 October 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1126 KB, uploaded 10 October 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. View Full-Text
Keywords: xylitan; xylitol; anhydropentitol; amastigote; trypomastigote; in vitro; chagas disease xylitan; xylitol; anhydropentitol; amastigote; trypomastigote; in vitro; chagas disease
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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MDPI and ACS Style

Elias, P.R.; Coelho, G.S.; Xavier, V.F.; Sales Junior, P.A.; Romanha, A.J.; Murta, S.M.F.; Carneiro, C.M.; Camilo, N.S.; Hilário, F.F.; Taylor, J.G. Synthesis of Xylitan Derivatives and Preliminary Evaluation of in Vitro Trypanocidal Activity. Molecules 2016, 21, 1342.

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