Synthesis and evaluation of D-gluco-pyranocyclopropyl amines as potential glucosidase inhibitors.
In the recent past sugar-derived cyclopropylamines were proposed as structurally new glycosidase inhibitors. In this Letter we report our efforts in the synthesis of a set of alpha-glucose configured oxabicyclo[4.1.0] heptanes, based on this hypothesis, bearing an amine substituent on the propyl ring and reveal that their inhibitory potential towards a range of mammalian glucosidases is modest.
Leiden Institute of Chemistry, Leiden University, Gorlaeus Laboratories, Einsteinweg 55, 2300 RA Leiden, The Netherlands.
Martijn D P
MD
Risseeuw
Richard J B H N
RJ
van den Berg
Wilma E
WE
Donker-Koopman
Gijs A
GA
van der Marel
Johannes M F G
JM
Aerts
Mark
M
Overhand
Herman S
HS
Overkleeft
D000588:Amines / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D019086:Bridged Bicyclo Compounds, Heterocyclic / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D004353:Drug Evaluation, Preclinical; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology*; D005959:Glucosidases / Q000037:antagonists & inhibitors*; D008968:Molecular Conformation; D013329:Structure-Activity Relationship
D000588:Amines; D019086:Bridged Bicyclo Compounds, Heterocyclic; D004791:Enzyme Inhibitors; D005959:Glucosidases