Síntese e avaliação da atividade citotóxica de derivados do eugenol contendo núcleos 1,2,3-triazólicos

Show simple item record Gazolla, Poliana Aparecida Rodrigues Teixeira, Róbson Ricardo Silva, Adalberto Manoel da Vaz, Boniek Gontijo Vasconcelos, Géssica Adriana Siqueira, Raoni Pais Gonçalves, Victor Hugo Sousa Pereira, Higor Sette Bressan, Gustavo Costa 2019-04-30T18:09:11Z 2019-04-30T18:09:11Z 2018-05
dc.identifier.issn 16787064
dc.description.abstract 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. en
dc.format pdf pt-BR
dc.language.iso por pt-BR
dc.publisher Química Nova pt-BR
dc.relation.ispartofseries v. 41, n. 05, pag. 497-506, mai. 2018 pt-BR
dc.rights Open Access pt-BR
dc.subject Eugenol pt-BR
dc.subject Triazole pt-BR
dc.subject Cytotoxic activity pt-BR
dc.subject Click chemistry pt-BR
dc.subject CuA pt-BR
dc.title Síntese e avaliação da atividade citotóxica de derivados do eugenol contendo núcleos 1,2,3-triazólicos pt-BR
dc.type Artigo pt-BR

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