Journal
EUROPEAN JOURNAL OF ORGANIC CHEMISTRY
Volume 2016, Issue 7, Pages 1429-1438Publisher
WILEY-V C H VERLAG GMBH
DOI: 10.1002/ejoc.201501453
Keywords
Azasugars; Iminosugar; Fluorine; Inhibitors; Structure-activity relationships; Drug design
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Funding
- National Basic Research Program of China [2012CB822101]
- National Natural Science Foundation of China (NSFC) [21202173, 21272240, 21102149]
- National Science and Technology Major Projects for Major New Drugs Innovation and Development [2013ZX09508104]
- Development Fund for Collaborative Innovation Center of Glycoscience of Shandong University
- National Engineering Research Center for Carbohydrate Synthesis of Jiangxi Normal University
- Leverhulme Emeritus Research Fellowship
- Japanese Society for the Promotion of Science (JSPS) [26460143]
- Grants-in-Aid for Scientific Research [26460143] Funding Source: KAKEN
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Fluorinated derivatives of radicamine A and radicamine B have been synthesized from D-arabinose-derived cyclic nitrone. Structure-activity relationship studies showed that glycosidase inhibition of these fluorinated derivatives was significantly influenced by the position of the fluorine atom. C-7 or C-11 fluorination of the aromatic ring decreased alpha-glucosidase inhibition of the derivatives, whereas C-8 or C-10 fluorination preserved glycosidase inhibitory activities.
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