Issue 7, 2016
From the journal:

Organic & Biomolecular Chemistry

Gem-difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars: synthesis and glycosidase inhibition†

Yi-Xian Li,a   Kyoko Kinami,b   Yuki Hirokami,b   Atsushi Kato,*b   Jia-Kun Su,a   Yue-Mei Jia,a   George W. J. Fleetcd  and  Chu-Yi Yu*ad  

* Corresponding authors

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
E-mail: yucy@iccas.ac.cn

b Department of Hospital Pharmacy, University of Toyama, 2630 Sugitani, Toyama 930-0194, Japan
E-mail: kato@med.u-toyama.ac.jp

c Chemistry Research Laboratory, Department of Chemistry, University of Oxford, Mansfield Road, Oxford, UK

d National Engineering Research Center for Carbohydrate Synthesis, Jiangxi Normal University, Nanchang 330022, PR China

Abstract

Gem-difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars have been synthesized from cyclic nitrones 12, 13, 18, ent-18 or 23 and nitrone-derived aldehydes 20 or ent-20. The fluorinated iminosugars were assayed against various glycosidases, and ent-8 showed moderate but selective α-L-rhamnosidase inhibition. Difluoro or trifluoro units influenced the inhibitory activities of iminosugars in a more complex manner than single fluoro substitution. This may be correlated with their highly hydrophobic character and strong electron-withdrawing effect.

Graphical abstract: Gem-difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars: synthesis and glycosidase inhibition

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Article information

DOI
https://doi.org/10.1039/C5OB02474A
Article type
Paper
Submitted
04 Dec 2015
Accepted
13 Jan 2016
First published
14 Jan 2016

Org. Biomol. Chem., 2016,14, 2249-2263

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Gem-difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars: synthesis and glycosidase inhibition

Y. Li, K. Kinami, Y. Hirokami, A. Kato, J. Su, Y. Jia, G. W. J. Fleet and C. Yu, Org. Biomol. Chem., 2016, 14, 2249 DOI: 10.1039/C5OB02474A

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