title: Difluoromethylenated polyhydroxylated pyrrolidines: facile synthesis, crystal structure and biological evaluation.
abstract: In our ongoing program aimed at the design, synthesis and biological evaluation of novel gem-difluoromethylenated glycosidase inhibitors, the gem-difluoromethylenated polyhydroxylated pyrrolidines as analogues of 2,5-dideoxy-2,5-imino-D-mannitol (DMDP) were designed and prepared. The crystal structure of gem-difluoromethylenated polyhydroxylated pyrrolidine 17 contains an N-H…F intermolecular hydrogen bond. The biological assessment of gem-difluoromethylenated polyhydroxylated pyrrolidines showed that the modification by the gem-difluoromethylene group decreased the inhibitory activities of DMDP.
authors.affiliation: Key Laboratory of Organofluorine Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Science, 345 lingling Lu, Shanghai 200032, China.
authors.forename: Ruo-Wen
authors.initials: RW
authors.lastname: Wang
authors.forename: Jun
authors.initials: J
authors.lastname: Xu
authors.forename: Oscar
authors.initials: O
authors.lastname: Lopez
authors.forename: Mikael
authors.initials: M
authors.lastname: Bols
authors.forename: Feng-Ling
authors.initials: FL
authors.lastname: Qing
mesh_terms: D018360:Crystallography, X-Ray; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005461:Fluorine / Q000737:chemistry; D006860:Hydrogen Bonding; D050112:Imino Pyranoses / Q000737:chemistry; D008353:Mannitol / Q000031:analogs & derivatives / Q000737:chemistry; D008968:Molecular Conformation; D011759:Pyrrolidines / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology; D000519:alpha-Galactosidase / Q000037:antagonists & inhibitors / Q000378:metabolism
chemical_list: C494911:2,5-dideoxy-2,5-imino-D-mannitol; D004791:Enzyme Inhibitors; D050112:Imino Pyranoses; D011759:Pyrrolidines; D005461:Fluorine; D008353:Mannitol; D000519:alpha-Galactosidase