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Molecules 2017, 22(4), 516; doi:10.3390/molecules22040516

Synthesis of Novel Saccharin Derivatives

Griffith Institute for Drug Discovery, Griffith University, Don Young Road, Nathan, Queensland 4111 Australia
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Received: 3 March 2017 / Revised: 20 March 2017 / Accepted: 20 March 2017 / Published: 23 March 2017
(This article belongs to the Special Issue Women in Organic Chemistry)
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Abstract

The 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. View Full-Text
Keywords: sulfonamide; metal binding group; zinc binding group; click chemistry; Cu(I)-catalyzed azide alkyne cycloaddition; saccharin; triazole; glycoconjugate sulfonamide; metal binding group; zinc binding group; click chemistry; Cu(I)-catalyzed azide alkyne cycloaddition; saccharin; triazole; glycoconjugate
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Rankin, G.M.; Poulsen, S.-A. Synthesis of Novel Saccharin Derivatives. Molecules 2017, 22, 516.

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