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Molecules 2016, 21(11), 1483; doi:10.3390/molecules21111483

Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol

1
Laboratório de Síntese Orgânica Medicinal da Paraíba (LASOM-PB), Departamento de Química, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, Brazil
2
Programa de Pós-graduação em Biologia Molecular and Departamento de Biologia Molecular, Centro de Ciências Exatas and da Natureza, Universidade Federal da Paraíba, João Pessoa, Paraíba CEP 58059-900, Brazil
3
Departamento de Biotecnologia, Universidade Federal da Paraíba, Campus I, João Pessoa, Paraíba CEP 58059-900, Brazil
*
Authors to whom correspondence should be addressed.
Academic Editor: Diego Muñoz-Torrero
Received: 11 October 2016 / Revised: 1 November 2016 / Accepted: 1 November 2016 / Published: 8 November 2016
(This article belongs to the Section Medicinal Chemistry)
View Full-Text   |   Download PDF [1580 KB, uploaded 8 November 2016]   |  

Abstract

Leishmaniasis represents a series of severe neglected tropical diseases caused by protozoa of the genus Leishmania and is widely distributed around the world. Here, we present the syntheses of Morita-Baylis-Hillman adducts (MBHAs) prepared from eugenol, thymol and carvacrol, and their bioevaluation against promastigotes of Leishmania amazonensis. The new MBHAs are prepared in two steps from essential oils in moderate to good yields and present IC50 values in the range of 22.30–4.71 μM. Moreover, the selectivity index to the most potent compound is very high (SIrb > 84.92), far better than that of Glucantime® (SIrb 1.39) and amphotericin B (SIrb = 22.34). Conformational analysis were carried out at the M062X//6-31+G(d,p) level of theory to corroborate a hypothesis about the nitroaromatic bioreduction mechanism. View Full-Text
Keywords: Morita-Baylis-Hillman adducts; Leishmania amazonensis; eugenol; thymol; carvacrol Morita-Baylis-Hillman adducts; Leishmania amazonensis; eugenol; thymol; carvacrol
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MDPI and ACS Style

Xavier, F.J.S.; Rodrigues, K.A.F.; de Oliveira, R.G.; Lima Junior, C.G.; Rocha, J.C.; Keesen, T.S.L.; de Oliveira, M.R.; Silva, F.P.L.; Vasconcellos, M.L.A.A. Synthesis and In Vitro Anti Leishmania amazonensis Biological Screening of Morita-Baylis-Hillman Adducts Prepared from Eugenol, Thymol and Carvacrol. Molecules 2016, 21, 1483.

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