Please use this identifier to cite or link to this item: http://hdl.handle.net/10316/33717
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dc.contributor.authorMachado, Nelson F. L.-
dc.contributor.authorCalheiros, Rita-
dc.contributor.authorFiuza, Sónia M.-
dc.contributor.authorBorges, Fernanda-
dc.contributor.authorGaspar, Alexandra-
dc.contributor.authorGarrido, Jorge-
dc.contributor.authorMarques, M. Paula M.-
dc.date.accessioned2016-12-20T10:40:52Z-
dc.date.available2016-12-20T10:40:52Z-
dc.date.issued2007-
dc.identifier10.1007/s00894-007-0174-y-
dc.identifier.urihttp://hdl.handle.net/10316/33717-
dc.description.abstractThe conformational preferences of several potential anticancer dihydroxycinnamic esters with a variable length alkyl chain were studied by quantum-mechanical (DFT) calculations (both for the isolated molecule and for aqueous solutions). The orientation of the hydroxyl ring substituents and of the alkyl ester moiety relative to the carbonyl group showed these to be the most determinant factors for the overall stability of this type of phenolic systems, strongly dependent on an effective pi-electron delocalization. Compared to the parent caffeic acid (dihydroxycinnamic acid), esterification was found to lead to a higher conformational freedom, and to affect mainly the energy barrier corresponding to the (O=)C-OR internal rotation. No particular differences were verified to occur upon lengthening of the ester alkyl chain, except when this is branched instead of linear. The vibrational spectra of the whole series of compounds were simulated, based on their calculated harmonic vibrational frequencies, and a preliminary assignment was performed.por
dc.language.isoengpor
dc.rightsopenAccesspor
dc.subjectAntineoplastic Agentspor
dc.subjectCoumaric Acidspor
dc.subjectEsterspor
dc.subjectModels, Molecularpor
dc.subjectMolecular Conformationpor
dc.subjectPhenolpor
dc.titlePhenolic esters with potential anticancer activity - the structural variablepor
dc.typearticle-
degois.publication.firstPage865por
degois.publication.lastPage877por
degois.publication.issue8por
degois.publication.titleJournal of Molecular Modelingpor
dc.peerreviewedyespor
degois.publication.volume13por
item.grantfulltextopen-
item.languageiso639-1en-
item.fulltextCom Texto completo-
Appears in Collections:FCTUC Ciências da Vida - Artigos em Revistas Internacionais
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