Synthesis, antiproliferative activities, and computational evaluation of novel isocoumarin and 3,4-dihydroisocoumarin derivatives

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dc.creatorKeller Guilherme Guimarães
dc.creatorRossimiriam Pereira de Freitas
dc.creatorAna Lúcia Tasca Gois Ruiz
dc.creatorGiovanna Francisco Fiorito
dc.creatorJoão Ernesto de Carvalho
dc.creatorElaine Fontes Ferreira da Cunha
dc.creatorTeodorico de Castro Ramalho
dc.creatorRosemeire Brondi Alves
dc.date.accessioned2024-07-16T18:13:23Z
dc.date.accessioned2025-09-09T00:44:36Z
dc.date.available2024-07-16T18:13:23Z
dc.date.issued2016
dc.description.sponsorshipCNPq - Conselho Nacional de Desenvolvimento Científico e Tecnológico
dc.description.sponsorshipFAPEMIG - Fundação de Amparo à Pesquisa do Estado de Minas Gerais
dc.description.sponsorshipCAPES - Coordenação de Aperfeiçoamento de Pessoal de Nível Superior
dc.description.sponsorshipOutra Agência
dc.identifier.doihttps://doi.org/10.1016/j.ejmech.2016.01.051
dc.identifier.issn1768-3254
dc.identifier.urihttps://hdl.handle.net/1843/70782
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofEuropean Journal of Medicinal Chemistry
dc.rightsAcesso Restrito
dc.subjectQuímica farmacêutica
dc.subjectSintese
dc.subjectHidrogenação
dc.subjectCélulas - Proliferação
dc.subjectCompostos orgânicos
dc.subject.otherIsocoumarin
dc.subject.other3,4-Dihydroisocoumarin
dc.subject.otherCastro–Stephens reaction
dc.subject.otherAntiproliferative
dc.titleSynthesis, antiproliferative activities, and computational evaluation of novel isocoumarin and 3,4-dihydroisocoumarin derivatives
dc.typeArtigo de periódico
local.citation.epage113
local.citation.spage103
local.citation.volume111
local.description.resumoA series of novel isocoumarin derivatives were synthesized using Castro–Stephens cross-coupling. Moreover, novel 3,4-dihydroisocoumarin derivatives were obtained by catalytic hydrogenation of the corresponding isocoumarin precursors. The antiproliferative activity of all compounds was evaluated in vitro in different tumor cells. Furthermore, docking calculations were performed for the kallikrein 5 (KLK5) active site to predict the possible mechanism of action of this series of compounds. Theoretical findings indicate that the 3,4-dihydroisocoumarin derivative 10a forms hydrogen bonds with Ser190 and Gln192 residues of KLK5. This derivative was the most active compound in the series with potent antiproliferative activity and high selectivity index (SI > 378.79) against breast cancer cells (MCF-7, GI50 = 0.66 μg mL−1). This compound represents a promising matrix for developing new antiproliferative agents.
local.identifier.orcidhttps://orcid.org/0000-0001-6974-3724
local.identifier.orcidhttps://orcid.org/0000-0002-0844-8702
local.identifier.orcidhttps://orcid.org/0000-0002-3845-3801
local.identifier.orcidhttps://orcid.org/0000-0002-7324-1353
local.identifier.orcidhttps://orcid.org/0000-0003-0546-2549
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://www.sciencedirect.com/science/article/pii/S0223523416300599

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