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Bioorg Med Chem Lett. 2014 Aug 1;24(15):3426-9. doi: 10.1016/j.bmcl.2014.05.079. Epub 2014 Jun 2.

Synthesis of bi-/tricyclic azasugars fused thiazinan-4-one and their HIV-RT inhibitory activity.

Author information

1
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China.
2
Key Laboratory of Chemical Biology of Hebei Province, College of Chemistry and Environmental Science, Hebei University, Baoding 071002, China. Electronic address: lixl@hbu.cn.

Abstract

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 0.49 μM. Structure-activity relationship analysis suggested that the phenyl group in the tricyclic azasugars was benefit for their anti-HIV RT activity.

KEYWORDS:

Anti-HIV RT activity; Bi-/tricyclic azasugar; Microwave radiation; Staudinger/aza-Wittig; Thiazinan-4-one

PMID:
24953602
DOI:
10.1016/j.bmcl.2014.05.079
[Indexed for MEDLINE]

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