Synthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities

dc.creatorTeixeira, Róbson Ricardo
dc.creatorGazolla, Poliana Aparecida Rodrigues
dc.creatorSilva, Adalberto Manoel da
dc.creatorBorsodi, Maria Paula Gonçalves
dc.creatorBergmann, Bartira Rossi
dc.creatorFerreira, Rafaela Salgado
dc.creatorVaz, Boniek Gontijo
dc.creatorVasconcelos, Géssica Adriana
dc.creatorLima, Wallace Pacienza
dc.date2018-04-24T16:45:44Z
dc.date2018-04-24T16:45:44Z
dc.date2018-01-15
dc.date.accessioned2023-09-27T21:13:43Z
dc.date.available2023-09-27T21:13:43Z
dc.identifier0223-5234
dc.identifierhttps://doi.org/10.1016/j.ejmech.2018.01.046
dc.identifierhttp://www.locus.ufv.br/handle/123456789/19082
dc.identifier.urihttps://repositorioslatinoamericanos.uchile.cl/handle/2250/8956937
dc.descriptionIn this paper, it is described the synthesis and the evaluation of the leishmanicidal activity of twenty-six eugenol derivatives bearing 1,2,3-triazole functionalities. The evaluation of the compounds on promastigotes of Leishmania amazonensis (WHOM/BR/75/Josefa) showed that eugenol derivatives present leishmanicidal activities with varying degrees of effectiveness. The most active compound, namely 4-(3-(4-allyl-2-methoxyphenoxy)propyl)-1-(4-methylbenzyl)-1H-1,2,3-triazole (7k) (IC50 = 7.4 ± 0.8 μmol L−1), also targeted Leishmania parasites inside peritoneal macrophages (IC50 = 1.6 μmol L−1) without interfering with cell viability. The cytotoxicity of 7k against macrophage cells presented IC50 of 211.9 μmol L−1 and the selective index was equal to 132.5. Under similar conditions, compound 7k was more effective than glucantime and pentamidine, two drugs currently in the clinic. In addition, theoretical calculations showed that this compound also presents most physicochemical and pharmacokinetic properties within the ranges expected for orally available drugs. It is believed that eugenol bearing 1,2,3-triazole functionalities may represent a scaffold to be explored toward the development of new agents to treat leishmaniasis.
dc.formatpdf
dc.formatapplication/pdf
dc.languageeng
dc.publisherEuropean Journal of Medicinal Chemistry
dc.relationv. 146, p. 274-286, February 2018
dc.rightsElsevier Masson SAS
dc.subjectEugenol
dc.subjectLeishmaniasis
dc.subjectAntileishmanial
dc.subjectLeishmanicidal
dc.subjectTriazole
dc.titleSynthesis and leishmanicidal activity of eugenol derivatives bearing 1,2,3-triazole functionalities
dc.typeArtigo


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