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dc.contributor.authorRankin, Gregory M
dc.contributor.authorPoulsen, Sally-Ann
dc.date.accessioned2017-07-25T12:31:07Z
dc.date.available2017-07-25T12:31:07Z
dc.date.issued2017
dc.identifier.issn1420-3049
dc.identifier.doi10.3390/molecules22040516
dc.identifier.urihttp://hdl.handle.net/10072/342196
dc.description.abstractThe synthesis of saccharin (1,2-benzisothiazol-3-one-1,1-dioxide) derivatives substituted on the benzene ring has seen limited development despite the longevity of this compound’s use as an artificial sweetener. This type of saccharin derivative would however present attractive properties for the development of new bioactive, drug-like small molecule compounds. Here we report the derivatisation of the benzene ring of saccharin using Cu(I)-catalyzed azide alkyne cycloaddition (CuAAC) to synthesise a diverse library of novel saccharin-1,2,3-triazole conjugates. All library compounds retain the capability for interactions with biomolecules via the unmodified sulfonamide and lactam groups of the parent saccharin core heterocycle. The compounds also encompass alternate orientations of the 1,2,3-triazole heterocycle, thus further adding diversity to the potential hydrogen bonding interactions of these compounds with biomolecules of therapeutic interest. Our findings demonstrate that specifically functionalized derivatives of saccharin may be prepared from either saccharin azide or saccharin alkyne building blocks in high yield using CuAAC.
dc.description.peerreviewedYes
dc.languageEnglish
dc.language.isoeng
dc.publisherMDPI AG
dc.relation.ispartofpagefrom516-1
dc.relation.ispartofpageto516-19
dc.relation.ispartofissue4
dc.relation.ispartofjournalMolecules
dc.relation.ispartofvolume22
dc.subject.fieldofresearchOrganic Chemistry not elsewhere classified
dc.subject.fieldofresearchMedicinal and Biomolecular Chemistry
dc.subject.fieldofresearchOrganic Chemistry
dc.subject.fieldofresearchTheoretical and Computational Chemistry
dc.subject.fieldofresearchcode030599
dc.subject.fieldofresearchcode0304
dc.subject.fieldofresearchcode0305
dc.subject.fieldofresearchcode0307
dc.titleSynthesis of Novel Saccharin Derivatives
dc.typeJournal article
dc.type.descriptionC1 - Articles
dc.type.codeC - Journal Articles
dcterms.licensehttp://creativecommons.org/licenses/by/4.0/
dc.description.versionVersion of Record (VoR)
gro.facultyGriffith Sciences, School of Natural Sciences
gro.rights.copyright© 2017 The Author(s). Licensee MDPI, Basel, Switzerland. This article is an open access article distributed under the terms and conditions of the Creative Commons Attribution (CC BY 4.0) license, which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.
gro.hasfulltextFull Text
gro.griffith.authorPoulsen, Sally-Ann
gro.griffith.authorRankin, Gregory


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