Iminecalix[4]arenes: microwave-assisted synthesis, x-ray crystal structures, and anticandidal activity

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dc.creatorCleiton Moreira da Silva
dc.creatorDanielle Letícia da Silva
dc.creatorThaís Furtado Ferreira Magalhães
dc.creatorRosemeire Brondi Alves
dc.creatorMaria Aparecida Resende Stoianoff
dc.creatorFelipe Terra Martins
dc.creatorÂngelo de Fátima
dc.date.accessioned2023-12-22T14:33:20Z
dc.date.accessioned2025-09-09T01:32:05Z
dc.date.available2023-12-22T14:33:20Z
dc.date.issued2019
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.doihttps://doi.org/10.1016/j.arabjc.2016.06.013
dc.identifier.issn1878-5352
dc.identifier.urihttps://hdl.handle.net/1843/62135
dc.languageeng
dc.publisherUniversidade Federal de Minas Gerais
dc.relation.ispartofArabian Journal of Chemistry
dc.rightsAcesso Aberto
dc.subjectCalixarenos
dc.subjectAntimicóticos
dc.subjectCristalografia de raio X
dc.subjectCandida
dc.subjectEspectrometria de massa
dc.subject.otherCalix[4]arene
dc.subject.otherAldimine
dc.subject.otherIminecalix[4]arenes microwave-assisted synthesis
dc.subject.otherAntifungal activity
dc.subject.otherX-ray crystal structure
dc.subject.otherPinched cone conformation
dc.titleIminecalix[4]arenes: microwave-assisted synthesis, x-ray crystal structures, and anticandidal activity
dc.typeArtigo de periódico
local.citation.epage4376
local.citation.issue8
local.citation.spage4365
local.citation.volume12
local.description.resumoIn this study, six iminecalix[4]arenes were synthesized and the crystal structures of two of the iminecalix[4]arenes were also determined. Iminecalix[4]arene adopts a strongly pinched cone conformation with two upper rim substituents pointing toward and the other two pointing away from the aromatic cavity. This uncommon conformation is stabilized by an intramolecular π…π interaction between the phenyl rings from the upper rim substituents pointing inwards the cone. In addition, phenyl rings from the substituent groups are not coplanar with respect to the calixarene phenyl rings holding them. The compounds, as well as their respective monomeric units, were evaluated for their antifungal activities against Candida strains. All the synthesized iminecalix[4]arenes were found to cause higher inhibition of all tested Candida strains than their respective monomers. The ratio between the minimal inhibitory concentration (MIC) of a monomer and the corresponding iminecalix[4]arene ranged from 2.05 to 36.50. Furthermore, the iminecalix[4]arene bearing nitrofuran group exhibited low MIC values comparable to that of fluconazole. Thus, this compound was twice more active than fluconazole against Candida krusei.
local.identifier.orcidhttps://orcid.org/0000-0001-9913-8971
local.identifier.orcidhttps://orcid.org/0000-0002-1447-6670
local.identifier.orcidhttps://orcid.org/0000-0003-0546-2549
local.identifier.orcidhttps://orcid.org/0000-0002-6220-1321
local.identifier.orcidhttps://orcid.org/0000-0003-2344-5590
local.publisher.countryBrasil
local.publisher.departmentICX - DEPARTAMENTO DE QUÍMICA
local.publisher.initialsUFMG
local.url.externahttp://www.sciencedirect.com/science/article/pii/S1878535216300910

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