Please use this identifier to cite or link to this item: https://doi.org/10.3390/molecules24081453
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dc.titleFused heterocyclic systems with an s-triazine ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines
dc.contributor.authorJunaid, A.
dc.contributor.authorLim, F.P.L.
dc.contributor.authorZhou, Y.P.
dc.contributor.authorChui, W.K.
dc.contributor.authorDolzhenko, A.V.
dc.date.accessioned2021-12-09T03:05:06Z
dc.date.available2021-12-09T03:05:06Z
dc.date.issued2019
dc.identifier.citationJunaid, A., Lim, F.P.L., Zhou, Y.P., Chui, W.K., Dolzhenko, A.V. (2019). Fused heterocyclic systems with an s-triazine ring. 34. Development of a Practical Approach for the Synthesis of 5-Aza-isoguanines. Molecules 24 (8) : 1453. ScholarBank@NUS Repository. https://doi.org/10.3390/molecules24081453
dc.identifier.issn1420-3049
dc.identifier.urihttps://scholarbank.nus.edu.sg/handle/10635/209983
dc.description.abstractPurine isosteres present excellent opportunities in drug design and development. Using isosteres of natural purines as scaffolds for the construction of new therapeutic agents has been a valid strategy of medicinal chemistry. Inspired by the similarity to isoguanine, we attempted to develop a practical method for the preparation of 5-aza-isoguanines. Several synthetic approaches were explored to establish a robust general protocol for the preparation of these compounds. The significant difference in the reactivity of the C-5 and C-7 electrophilic centers of 1,2,4-triazolo[1,5-a][1,3,5]triazines (5-azapurines) towards nucleophiles was demonstrated. The most practical and general method for the preparation of 5-aza-isoguanines involved a regioselective reaction of ethoxycarbonyl isothiocyanate with a 5-aminotriazole. The intramolecular ring closure of the resulted product followed by the S-methylation afforded 7-methylthio-2-phenyl-1,2,4-triazolo[1,5-a][1,3,5]triazin-5-one, which could be effectively aminated with various amines. The resulted 5-aza-isoguanines resemble a known purine nucleoside phosphorylase inhibitor and could be interesting for further investigations as potential anticancer agents. © 2019 by the authors.
dc.publisherMDPI AG
dc.rightsAttribution 4.0 International
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.sourceScopus OA2019
dc.subjectAzapurine
dc.subjectPurine isostere
dc.subjectTriazine
dc.subjectTriazole
dc.typeArticle
dc.contributor.departmentDEPT OF PHARMACY
dc.description.doi10.3390/molecules24081453
dc.description.sourcetitleMolecules
dc.description.volume24
dc.description.issue8
dc.description.page1453
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