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

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dc.creatorGazolla, Poliana Aparecida Rodrigues
dc.creatorTeixeira, Róbson Ricardo
dc.creatorSilva, Adalberto Manoel da
dc.creatorVaz, Boniek Gontijo
dc.creatorVasconcelos, Géssica Adriana
dc.creatorSiqueira, Raoni Pais
dc.creatorGonçalves, Victor Hugo Sousa
dc.creatorPereira, Higor Sette
dc.creatorBressand, Gustavo Costa
dc.date.accessioned2023-07-03T15:29:07Z
dc.date.available2023-07-03T15:29:07Z
dc.date.issued2018-02-22
dc.description.abstractEugenol 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.pt_BR
dc.identifier.citationGAZOLLA, 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.pt_BR
dc.identifier.doi10.21577/0100-4042.20170206
dc.identifier.issne- 1678-7064
dc.identifier.issn0100-4042
dc.identifier.urihttp://repositorio.bc.ufg.br/handle/ri/22872
dc.language.isoporpt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentInstituto de Química - IQ (RMG)pt_BR
dc.rightsAcesso Abertopt_BR
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectEugenolpt_BR
dc.subjectTriazolept_BR
dc.subjectCytotoxic activitypt_BR
dc.subjectClick chemistrypt_BR
dc.subjectCuAAC reactionpt_BR
dc.titleSíntese e avaliação da atividade citotóxica de derivados do eugenol contendo núcleos 1,2,3-triazólicospt_BR
dc.title.alternativeSynthesis and cytotoxic activity of 1,2,3-triazole derivatives of eugenolpt_BR
dc.typeArtigopt_BR

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