Stereoselective synthesis of (2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol derivatives that are highly selective alpha-L-fucosidase inhibitors.
N-Phenylaminomethyl benzimidazolyl moieties attached at C-2 of (2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol increase the potency and selectivity of the inhibitory activity of these systems towards alpha-L-fucosidases.
Moreno-Vargas
Antonio J
AJ
Department of Organic Chemistry, Faculty of Chemistry, University of Seville, P. O. Box 553, E-41071 Seville, Spain.
Carmona
Ana T
AT
Mora
Federico
F
Vogel
Pierre
P
Robina
Inmaculada
I
D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D015394:Molecular Structure; D011759:Pyrrolidines / Q000032:analysis* / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism; D005644:alpha-L-Fucosidase / Q000037:antagonists & inhibitors* / Q000378:metabolism
C517931:(2S,3S,4R,5S)-5-methylpyrrolidine-3,4-diol; D004791:Enzyme Inhibitors; D011759:Pyrrolidines; D005644:alpha-L-Fucosidase