Síntese e avaliação da atividade citotóxica de derivados do eugenol contendo núcleos 1,2,3-triazólicos
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2018-02-22
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Resumo
Eugenol is an aromatic
compound found in several plant species. It presents important biological activities including cytotoxicity. In this paper, it is
described the synthesis and the evaluation of the cytotoxic activity of eugenol derivatives bearing 1,2,3-triazole functionalities.
Eugenol, extracted via hydrodistillation from dried flower buds of Eugenia caryophyllata (=Syzygium aromaticum), was submitted
to alkylation reactions to afford two terminal alkynes in good yields. The key reaction involved in the preparation of eugenol
derivatives corresponded to the Copper(I)-catalyzed Azide-Alkyne Cycloaddition (CuAAC), between alkynylated eugenol derivatives
and different benzyl azides. The evaluation of the cytotoxicity of twenty seven synthesized derivatives against HL60 leukemia
cell line revealed that at 100 µmol L-1, five of them, namely 4-((4-allyl-2-methoxyphenoxy)methyl)-1-(3-bromobenzyl)-1H-1,2,3-
triazole (6n), 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-benzyl-1H-1,2,3-triazole (7a), 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-
1-(4-chlorobenzyl)-1H-1,2,3-triazole (7c), 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-iodobenzyl)-1H-1,2,3-triazole (7e) and
4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(3-bromobenzyl)-1H-1,2,3-triazole (7m), were capable of significantly decreasing cell
viability. These most active triazolic derivatives were also evaluated against B16F10 melanoma and Nalm6 leukemia cell lines.
While only compound 7a was active against the former, compounds 6n, 7a, and 7m displayed activity against the latter. Derivative
7a was active against all cell lines. It is believed that eugenol derivatives bearing triazole functionalities may represent a scaffold to
be explored toward the development of new agents against cancer.
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Palavras-chave
Eugenol, Triazole, Cytotoxic activity, Click chemistry, CuAAC reaction
Citação
GAZOLLA, Poliana Aparecida Rodrigues et al. Síntese e avaliação da atividade citotóxica de derivados do eugenol contendo núcleos 1,2,3-triazólicos. Química Nova, São Paulo, v. 41, n. 5, p. 497-506, 2018. DOI: 10.21577/0100-4042.20170206. Disponível em: https://quimicanova.sbq.org.br/detalhe_artigo.asp?id=6759. Acesso em: 21 jun. 2023.