Sintese e atividade biologica de analogos furanicos da goniotalamina / Synthesis and biological activity of furan analogues of goniothalamin

AUTOR(ES)

Cilene Marquissolo

FONTE

IBICT - Instituto Brasileiro de Informação em Ciência e Tecnologia

DATA DE PUBLICAÇÃO

07/07/2009

RESUMO

This work describes the preparation of furan analogues of goniothalamin (compounds 31, 32 and 33) in both enantiomeric forms through the utilization of Keck asymmetric allylation and ring-closing methatesis reaction. These analogues were prepared in good overall yield and excellent enantiomeric ratio. These novel compounds were evaluated as antiproliferative agents against a panel of nine cancer cell lines and in vitro bioassays against the tripomastigote form of Trypanosoma cruzi and promastigote form of Leishmania major and Leishmania brasiliensis. Compounds 31-33 were more potent than the positive control (doxorubicin) in the antiproliferative experiments, except for melanoma and colon cancer cells. Additionally compounds 31-33 were more active than goniothalamin (1), except for breast and ovary cancer cells. Regarding their tripanocidal activity, compound (S)-31 was shown to be very toxic to non-infected cells despite its being highly active. Compound (S)-32 was the most promising one against T. cruzi due to its low toxicity and high insurance level. As to the leishmanicidal activity, the analogue (S)-31 was shown to be the most active for both Leishmania species investigated being 6,5 times more active than the positive control for Leishmania brasiliensis and about 14,6 times for Leishmania major, The citotoxicity assays revealed low toxicity against non-infected cells. For Leishmania brasiliensis and Leishmania major (R)-31 and (S)-31 were shown to be more active one and also displayed the best insurance level. Analogue 33 did not display any significant biological activity in our assays indicating that the nitrofuran moiety is very important for the biological activities investigated.

ASSUNTO(S)

goniotalamina analogos furanicos sintese catalitica assimetrica atividade biologica goniothalamin furan analogues catalytic asymmetric synthesis biological activity

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