title: Gem-difluoromethylated and trifluoromethylated derivatives of DMDP-related iminosugars: synthesis and glycosidase inhibition.
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.
authors.affiliation: 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. yucy@iccas.ac.cn.
authors.forename: Yi-Xian
authors.initials: YX
authors.lastname: Li
authors.forename: Kyoko
authors.initials: K
authors.lastname: Kinami
authors.forename: Yuki
authors.initials: Y
authors.lastname: Hirokami
authors.forename: Atsushi
authors.initials: A
authors.lastname: Kato
authors.forename: Jia-Kun
authors.initials: JK
authors.lastname: Su
authors.forename: Yue-Mei
authors.initials: YM
authors.lastname: Jia
authors.forename: George W J
authors.initials: GW
authors.lastname: Fleet
authors.forename: Chu-Yi
authors.initials: CY
authors.lastname: Yu
mesh_terms: D005617:Chlorofluorocarbons, Methane / Q000138:chemical synthesis / Q000737:chemistry*; D003500:Cyclization; D006026:Glycoside Hydrolases / Q000037:antagonists & inhibitors*; D006845:Hydrocarbons, Fluorinated / Q000138:chemical synthesis / Q000737:chemistry*; D050113:Imino Furanoses / Q000138:chemical synthesis / Q000737:chemistry*; D015394:Molecular Structure; D009589:Nitrogen Oxides / Q000737:chemistry*
chemical_list: D005617:Chlorofluorocarbons, Methane; D006845:Hydrocarbons, Fluorinated; D050113:Imino Furanoses; D009589:Nitrogen Oxides; C015388:nitrones; C102075:difluoromethane; D006026:Glycoside Hydrolases; C009554:fluoroform