Synthesis, antileishmanial activity and spin labeling EPR studies of novel β-carboline-oxazoline and β-carboline-dihydrooxazine derivatives

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dc.creatorBaréa, Paula
dc.creatorRomoli, Jéssica Cristina Zoratto
dc.creatorAlonso, Lais
dc.creatorOliveira, Aline R. de
dc.creatorCosta, Willian Ferreira da
dc.creatorAlonso, Antonio
dc.creatorNakamura, Celso Vataru
dc.creatorSarragiotto, Maria Helena
dc.date.accessioned2023-04-17T11:25:10Z
dc.date.available2023-04-17T11:25:10Z
dc.date.issued2020
dc.description.abstractA series of novel 1-(substituted-phenyl)-3-(4,5-dihydro-1,3-oxazol-2-yl)-9H-β-carboline (8a-8i) and 1-(substituted-phenyl)-3-(5,6-dihydro-4H-1,3-oxazin-2-yl)-9H-β-carboline (9a-9h) derivatives, as well as their respective N-(chloroalkyl)-1-(substituted-phenyl)-9H-β-carboline-3-carboxamide precursors (6a-6i and 7a-7h), were synthesized and evaluated for their in vitro antileishmanial activity against promastigote and intracellular amastigote forms of Leishmania amazonensis. Compounds 8d, 8i, 9e and 9h exhibited significant activity for both promastigote and amastigote forms, with IC50 (50% inhibitory concentration) values ranging from 2.9 to 23.0 μM. In addition, spin label electron paramagnetic resonance (EPR) spectroscopy studies were carried out for the most active compounds against L. amazonensis promastigotes. The studies indicated that the tested compounds cause strong stiffness in the parasite plasma membrane and are capable of inducing internal metalloproteins oxidation of the parasite, resulting in their cross-linking to skeletal proteins. Compounds 8d and 8i produced the largest effect, showing that the presence of oxazoline group at C-3 of β-carboline nucleus is important for antileishmanial activity.pt_BR
dc.identifier.citationBARÉA, Paula; PAULA, Jéssica C. de; ALONSO, Laís; OLIVEIRA, Aline R. de; COSTA, Willian F. da; Alonso, Antonio; NAKAMURA, Celso V.; SARRAGIOTTO, Maria H. Synthesis, antileishmanial activity and spin labeling EPR studies of novel β-carboline-oxazoline and β-carboline-dihydrooxazine derivatives. Journal of the Brazilian Chemical Society, Campinas, v. 31, n. 6, p. , 1170-1185, 2020. Disponível em: https://s3.sa-east-1.amazonaws.com/static.sites.sbq.org.br/jbcs.sbq.org.br/pdf/2019-0581AR.pdf. Acesso em: 14 abr. 2023.pt_BR
dc.identifier.issne- 0103-5053
dc.identifier.urihttp://repositorio.bc.ufg.br/handle/ri/22355
dc.language.isoengpt_BR
dc.publisher.countryBrasilpt_BR
dc.publisher.departmentInstituto de Física - IF (RG)pt_BR
dc.rightsAcesso Abertopt_BR
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.subjectβ-carbolinept_BR
dc.subject4,5-dihydro-1,3-oxazolept_BR
dc.subject5,6-dihydro-4H-1,3-oxazinept_BR
dc.subjectElectron paramagnetic resonancept_BR
dc.subjectLeishmania amazonensispt_BR
dc.titleSynthesis, antileishmanial activity and spin labeling EPR studies of novel β-carboline-oxazoline and β-carboline-dihydrooxazine derivativespt_BR
dc.typeArtigopt_BR

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