Gem-difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars: synthesis and glycosidase inhibition. Issue 7 (21st January 2016)

• Record Type: Journal Article
• Authors: Li, Yi-Xian; Kinami, Kyoko; Hirokami, Yuki; Kato, Atsushi; Su, Jia-Kun; Jia, Yue-Mei; Fleet, George W. J.; Yu, Chu-Yi
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 7(2016)
• Page Start: 2249
• Page End: 2263
• Publication Date: 2016-01-21
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c5ob02474a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : Gem -difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars have been synthesized from cyclic nitrones and assayed against various glycosidases. Abstract : Gem -difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars have been synthesized from cyclic nitrones12, 13, 18, ent -18 or23 and nitrone-derived aldehydes20 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.