期刊
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
卷 2011, 期 36, 页码 7390-7399出版社
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201100859
关键词
Medicinal chemistry; Antiviral agents; Nucleosides; Metathesis; Glycosylation; Nitrogen heterocycles
资金
- Centre National de la Recherche Scientifique (CNRS)
- Universite de Nantes
- US National Institutes of Health (NIH) [2P30-AI-050409, 5R37-AI-025899, 5R37-AI-041980]
- Department of Veterans Affairs
A set of pyrimidine nucleosides fused with a 4'-C,3'-O-propylene bridge was successfully synthesised in 12 steps from 1,2:5,6-di-O-isopropylidene-alpha-D-glucofuranose, an inexpensive starting material, based on a ring-closing metathesis (RCM) reaction followed by Vorbruggen-type nucleobase coupling. Antiviral and cytotoxicity activities of the targeted modified nucleosides, as well as their phosphoramidate prodrugs, are described.
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