Aminocyclopentanols as sugar mimics. Synthesis from unsaturated bicyclic lactones by Overman rearrangement.
Bicyclic cyclopentane lactones, prepared from bromodeoxyaldonolactones, were transformed into aminocyclopentanols with an Overman rearrangement as the key step. Two of the compounds prepared, 7 and 19, were found to be good inhibitors of jack bean alpha-mannosidase and beta-D-N-acetylglucosaminidase, respectively.
Bøjstrup
Marie
M
Department of Chemistry, Technical University of Denmark, Building 201, DK-2800, Kgs Lyngby, Denmark.
Fanefjord
Mette
M
Lundt
Inge
I
D000118:Acetylglucosaminidase / Q000037:antagonists & inhibitors*; D003517:Cyclopentanes / Q000138:chemical synthesis* / Q000494:pharmacology; D004791:Enzyme Inhibitors / Q000138:chemical synthesis*; D007783:Lactones / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D043323:alpha-Mannosidase / Q000037:antagonists & inhibitors*
D003517:Cyclopentanes; D004791:Enzyme Inhibitors; D007783:Lactones; C016327:cyclopentanol; D043323:alpha-Mannosidase; D000118:Acetylglucosaminidase