Regiospecific route to N9-alkylated thioxanthines

A regiospecific route to N9-alkylated thioxanthines as novel acyclic nucleoside analogues has been developed. This approach is based on a cleavage methodology involving the construction of a target heterocyclic scaffold based on a 1,3,4-2H-thiadiazole moiety, which is subsequently cleaved under basi...

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Bibliographic Details
Published inNew journal of chemistry Vol. 46; no. 36; pp. 17145 - 17148
Main Authors Savateev, Konstantin, Fedotov, Victor V., Slepukhin, Pavel A., Ulomsky, Evgeniy N., Rusinov, Vladimir L.
Format Journal Article
LanguageEnglish
Published CAMBRIDGE Royal Soc Chemistry 20.09.2022
Royal Society of Chemistry
Subjects
Alkylation
Chemistry
Chemistry, Multidisciplinary
Column chromatography
Physical Sciences
Science & Technology
Thiadiazoles
NUCLEOSIDE
DESIGN
PURINE
BIOSYNTHESIS
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Summary:A regiospecific route to N9-alkylated thioxanthines as novel acyclic nucleoside analogues has been developed. This approach is based on a cleavage methodology involving the construction of a target heterocyclic scaffold based on a 1,3,4-2H-thiadiazole moiety, which is subsequently cleaved under basic conditions. The procedure is performed under mild scalable conditions excluding column chromatography purification, with readily available precursors, and results in good to excellent yields of the target thioxanthines along with an analogue of the marketed drug penciclovir.
ISSN:1144-0546
1369-9261
DOI:10.1039/d2nj03002k