340699-25-4Relevant articles and documents
Stereoisomeric imidazolo-pentoses - Synthesis, chiroptical properties, and evaluation as glycosidase inhibitors
Tschamber, Theophile,Siendt, Herve,Boiron, Arnaud,Gessier, Francois,Deredas, Dariusz,Frankowski, Andrzej,Picasso, Sylviane,Steiner, Heinz,Aubertin, Anne-Marie,Streith, Jacques
, p. 1335 - 1347 (2007/10/03)
The syntheses of all four imidazolo-piperidino-pentoses in the L-series ent-2 to ent-5, and of three out of the four possible stereomers in the D-series 3, 4, and 5, are reported. The linear imidazolo sugar precursors were prepared, either by double condensation of formamidine with protected aldohexoses, or by nucleophilic addition of a lithiated imidazole derivative to protected aldotetroses. Cyclisation of these linear imidazolo-carbohydrates was performed by intramolecular SN2 reactions. These were followed by deprotection to the target molecules. The four pairs of opposite enantiomers showed pronounced mirror-image-type Cotton effects in their CD spectra. All stereomers of the D-series show a negative rotatory power ([α]D), while the stereomers of the L-series show a positive one. None of the eight imidazolo sugars inhibited the replication of HIV-1. Some of them proved to be rather selective but only moderately potent inhibitors of α-glycosidases, as determined by Michaelis-Menten kinetics.
