Natural organic acid as green catalyst for xanthenones synthesis: methodology, mechanism and calcium channel blocking activity

dc.creatorBruna Silva Terra Diniz
dc.creatorDaniella Bonaventura
dc.creatorHeitor Avelino de Abreu
dc.creatorAntônio Flávio de Carvalho Alcântara
dc.creatorÂngelo de Fátima
dc.creatorAura María Blandón Osorio
dc.creatorAline de Oliveira
dc.creatorRebeca Priscila de Melo Santos
dc.creatorAndressa Pereira Mouro
dc.creatorNatália Ferreira de Araújo
dc.creatorCameron Capeletti da Silva
dc.creatorFelipe Terra Martins
dc.creatorLuciene Bruno Vieira
dc.date.accessioned2024-07-09T18:30:05Z
dc.date.accessioned2025-09-09T00:24:57Z
dc.date.available2024-07-09T18:30:05Z
dc.date.issued2017
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.format.mimetypepdf
dc.identifier.doihttp://dx.doi.org/10.21577/0103-5053.20170082
dc.identifier.issn0103-5053
dc.identifier.urihttps://hdl.handle.net/1843/69920
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofJournal of the Brazilian Chemical Society
dc.rightsAcesso Aberto
dc.subjectÁcidos orgânicos
dc.subjectAldeídos
dc.subjectFenóis
dc.subjectXantona
dc.subjectSuperfícies de energia potencial
dc.subjectEspectros vibracionais
dc.subject.otherXanthenones
dc.subject.otherNatural organic acid
dc.subject.otherTheoretical calculations
dc.subject.otherCalcium channels blockers
dc.titleNatural organic acid as green catalyst for xanthenones synthesis: methodology, mechanism and calcium channel blocking activity
dc.typeArtigo de periódico
local.citation.epage2325
local.citation.issue12
local.citation.spage2313
local.citation.volume28
local.description.resumoXanthenones were synthesized via one-pot tricomponent reaction, under solvent-free conditions, using aldehydes, phenolic and cyclic 1,3-dicarbonyl compounds. Natural organic acids (NOAs), compounds present in many living metabolisms, were used as potential green catalysts. NOA are considered to be more eco-friendly and user-friendly alternative to traditional methodologies. Optimization studies showed that oxalic acid was the best NOA catalyst for such reaction furnishing the xanthenones with up to 93% of yield. Theoretical calculations were performed to evaluate this reaction mechanism and regioselectivity. The results showed that the regiospecificity of this three-component reaction is kinetically and thermodynamically controlled by the addition of b-naphthol C2, instead of C10, to the aldehyde. Our results also disclosed two xanthenones as novel calcium channels blockers. Eco-friendly reaction conditions, easy workup procedure, short reaction times and good yields are some of the advantages of our methodology.
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.identifier.orcidhttps://orcid.org/0000-0001-5253-4918
local.identifier.orcidhttps://orcid.org/0000-0003-1971-9675
local.identifier.orcidhttps://orcid.org/0000-0001-5175-8370
local.publisher.countryBrasil
local.publisher.departmentICB - DEPARTAMENTO DE FARMACOLOGIA
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttps://jbcs.sbq.org.br/default.asp?ed=260

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