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Synthesis and in vitro anti-hepatitis B virus activity of six-membered azanucleoside analogues

Authors :
Wang, Dan
Li, Yu-Huan
Wang, Yu-Ping
Gao, Rong-Mei
Zhang, Li-He
Ye, Xin-Shan
Source :
Bioorganic & Medicinal Chemistry. Jan2011, Vol. 19 Issue 1, p41-51. 11p.
Publication Year :
2011

Abstract

Abstract: Fifteen novel six-membered azanucleoside derivatives were prepared and evaluated for their anti-hepatitis B virus (HBV) activity and cytotoxicity in human hepatoblastoma-derived liver Hep-G2 cells. The most potent compound 16b with an IC50 value of 2.74μg/mL (lower than 3TC) and a SI value of 13.5 was disclosed. The key synthetic steps involved the rearrangement of lactones (which were readily obtained from monosaccharides) and the Lewis acid-catalyzed condensation of nucleobases with azasugar donors. Using the versatile acetylated azasugar donors, azanucleosides covering three types of azasugars and four types of natural nucleobases were successfully obtained. The experimental results showed that some six-membered azanucleosides may find applications in the discovery of new anti-viral agents. [ABSTRACT FROM AUTHOR]

Details

Language :
English
ISSN :
09680896
Volume :
19
Issue :
1
Database :
Academic Search Index
Journal :
Bioorganic & Medicinal Chemistry
Publication Type :
Academic Journal
Accession number :
57251700
Full Text :
https://doi.org/10.1016/j.bmc.2010.11.063