Citation: Hui Zhao, Wu-Bao Wang, Shinpei Nakagawa, Yue-Mei Jia, Xiang-Guo Hu, George W.J. Fleet, Francis X. Wilson, Robert J. Nash, Atsushi Kato, Chu-Yi Yu. Novel 2-aryl-3,4,5-trihydroxypiperidines: Synthesis and glycosidase inhibition[J]. Chinese Chemical Letters, ;2013, 24(12): 1059-1063. shu

Novel 2-aryl-3,4,5-trihydroxypiperidines: Synthesis and glycosidase inhibition

1.
a Beijing National Laboratory for Molecular Science (BNLMS), CAS Key Laboratory of Molecular Recognition and Function, Institute of Chemistry, Chinese Academy of Sciences, Beijing 100190, China;
2.
b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan;
3.
c Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK;
4.
d Summit PLC, 91, Milton Park, Abingdon, Oxon OX14 4RY, UK;
5.
e Phytoquest Limited, IBERS, Plas Gogerddan, Ceredigion, Aberystwyth SY23 3EB, Wales, UK

Corresponding author: Atsushi Kato, Chu-Yi Yu,
Received Date: 19 May 2013
Available Online: 6 June 2013
Fund Project:

Three pairs of novel 2-aryl-3,4,5-trihydroxypiperidines (6-8 and their enantiomers), the piperidine analogues of the pyrrolidine alkaloids radicamine A and radicamine B, were prepared from sixmembered cyclic nitrones through a concise two-step procedure, i.e., Grignard reagent addition and deprotection. These novel polyhydroxylated piperidine iminosugars were assayed against 10 types of enzymes. Only compound 8 exhibited weak inhibition (IC₅₀ 1080 μmol/L) against β-galactosidase from rat intestinal lactases.
- 2-Aryl polyhydroxylated piperidine,
- Iminosugars,
- Radicamine mimics,
- Glycosidase inhibitors
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