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Synthesis and Evaluation of Antimalarial Activity of Oxygenated 3-alkylpyridine Marine Alkaloid Analogues

Authors

  • Flaviane F. Hilário,

    1. Departamento de Química, ICEx, UFMG, Av. Pres. Antonio Carlos, 6627, Pampulha, Belo Horizonte, MG, 31270-901, Brazil
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  • Renata Cristina de Paula,

    1. Universidade Federal de São João del Rei - Campus Centro-Oeste, Av. Sebastião Gonçalves Coelho, 400, Divinópolis, MG, 35501-296, Brazil
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  • Mariana L. T. Silveira,

    1. Departamento de Química, ICEx, UFMG, Av. Pres. Antonio Carlos, 6627, Pampulha, Belo Horizonte, MG, 31270-901, Brazil
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  • Gustavo H. R. Viana,

    1. Universidade Federal de São João del Rei - Campus Centro-Oeste, Av. Sebastião Gonçalves Coelho, 400, Divinópolis, MG, 35501-296, Brazil
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  • Rosemeire B. Alves,

    1. Departamento de Química, ICEx, UFMG, Av. Pres. Antonio Carlos, 6627, Pampulha, Belo Horizonte, MG, 31270-901, Brazil
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  • Juliana R. C. S. Pereira,

    1. Universidade Federal de São João del Rei - Campus Centro-Oeste, Av. Sebastião Gonçalves Coelho, 400, Divinópolis, MG, 35501-296, Brazil
    2. Laboratório de Biologia Celular e Inovação Biotecnológica, Fundação Ezequiel Dias, R. Conde Pereira Carneiro, 80, Belo Horizonte, MG, 30535-380, Brazil
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  • Luciana Maria Silva,

    1. Laboratório de Biologia Celular e Inovação Biotecnológica, Fundação Ezequiel Dias, R. Conde Pereira Carneiro, 80, Belo Horizonte, MG, 30535-380, Brazil
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  • Rossimiriam P. de Freitas,

    Corresponding author
    1. Departamento de Química, ICEx, UFMG, Av. Pres. Antonio Carlos, 6627, Pampulha, Belo Horizonte, MG, 31270-901, Brazil
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  • Fernando de Pilla Varotti

    Corresponding author
    1. Universidade Federal de São João del Rei - Campus Centro-Oeste, Av. Sebastião Gonçalves Coelho, 400, Divinópolis, MG, 35501-296, Brazil
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Corresponding authors: Rossimiriam P. de Freitas, rossi@netuno.lcc.ufmg.br and Fernando de Pilla Varotti, varotti@ufsj.edu.br

Abstract

A series of new oxygenated analogues of marine 3-alkylpyridine alkaloids were prepared from 3-pyridinepropanol in few steps and in good yields. The key step for the synthesis of these compounds was a Williamson etherification under phase-transfer conditions. All new compounds were evaluated for their antiplasmodial activity and cytotoxicity. A significant reduction in parasitaemia was observed for some of the prepared compounds, and the majority of them exhibited a selectivity index (SI) ranging from 2.78 to 15.58, which suggests that these compounds may be a promising class of substances with antimalarial activity.

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