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dc.contributor.authorSardella, R
dc.contributor.authorIanni, F
dc.contributor.authorDi Michele, A
dc.contributor.authorDi Capua, A
dc.contributor.authorCarotti, A
dc.contributor.authorAnzini, M
dc.contributor.authorNatalini, B
dc.date.accessioned2017-08-11T12:30:48Z
dc.date.available2017-08-11T12:30:48Z
dc.date.issued2017
dc.identifier.issn0899-0042
dc.identifier.doi10.1002/chir.22724
dc.identifier.urihttp://hdl.handle.net/10072/343842
dc.description.abstractThe capacity of nonsteroidal antiinflammatory drugs (NSAIDs) to prevent prostanoids biosynthesis through the inhibition of COX-2 enzyme is related to their structural backbone, based on the fusion of a cis-stilbene unit with a variety of heterocyclic and carbocyclic rings. By this route, a series of new selective COX-2 inhibitors was developed, by maintaining the 4-methylsulfone or 4-methylsulfonamide substituent on the phenyl moiety, essential for their activity. In this frame, two novel propyl sulfoxide derivatives were synthesized, which proved selective and sufficiently potent COX-2 inhibition activity when tested as racemates. In the present study, the use of a cellulose tris(3,5-dichlorophenylcarbamate)-based chiral stationary phase, in a polar-organic mode of elution, enabled the successful enantioseparation of the investigated compounds. The developed chromatography method reveals a useful tool of monitoring in view of a proper forthcoming enantioselective synthetic protocol. Moreover, the optimized chromatographic conditions allowed the isolation of appropriate amounts of single enantiomers for the electronic circular dichroism studies that, coupled with in silico simulations, allowed assessing the absolute configuration of each species.
dc.description.peerreviewedYes
dc.languageEnglish
dc.language.isoeng
dc.publisherWiley-Blackwell
dc.relation.ispartofpagefrom1
dc.relation.ispartofpageto5
dc.relation.ispartofjournalChirality
dc.subject.fieldofresearchAnalytical chemistry
dc.subject.fieldofresearchOrganic chemistry
dc.subject.fieldofresearchOrganic chemistry not elsewhere classified
dc.subject.fieldofresearchPhysical chemistry
dc.subject.fieldofresearchcode3401
dc.subject.fieldofresearchcode3405
dc.subject.fieldofresearchcode340599
dc.subject.fieldofresearchcode3406
dc.titleEnantioresolution and stereochemical characterization of two chiral sulfoxides endowed with COX-2 inhibitory activity
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
gro.description.notepublicThis publication has been entered into Griffith Research Online as an Advanced Online Version.
gro.hasfulltextNo Full Text
gro.griffith.authorDi Capua, Angela


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