Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity.
Bioorganic & Medicinal Chemistry Letters(2014)
摘要
Novel bi-/tricyclic azasugars fused thiazinan-4-one were conveniently synthesized by the tandem Staudinger/aza-Wittig/cyclization reaction under microwave radiation. The aryl group (phenyl or pyridyl) in mercaptan acid had an important effect on the formation of the diastereomers of the tricyclic hybrids 12b–15b. The new bi/tricyclic azasugars 3a–8a, 4b, 6b, 8b and the known ones 2a, 2b were examined for their HIV reverse transcriptase (RT) inhibitory activities. The result showed that compounds 2a–b, 4a, 4b, 5a, and 6a could effectively inhibit RT activity. Among them, the tricyclic azasugar 5a was the best one with the IC50 value of 0.49μM. Structure–activity relationship analysis suggested that the phenyl group in the tricyclic azasugars was benefit for their anti-HIV RT activity.
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关键词
Bi-/tricyclic azasugar,Thiazinan-4-one,Staudinger/aza-Wittig,Anti-HIV RT activity,Microwave radiation
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