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 α-glucose configured oxabicyclo[4.1.0] heptanes, based on this hypothesis, bearing an amine substituent on the propyl ring an...

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Veröffentlicht in:	Bioorganic & medicinal chemistry letters 2009-12, Vol.19 (23), p.6600-6603
Hauptverfasser:	Risseeuw, Martijn D.P., van den Berg, Richard J.B.H.N., Donker-Koopman, Wilma E., van der Marel, Gijs A., Aerts, Johannes M.F.G., Overhand, Mark, Overkleeft, Herman S.
Format:	Artikel
Sprache:	eng
Schlagworte:	Amines - chemical synthesis Amines - chemistry Amines - pharmacology Biological and medical sciences Bridged Bicyclo Compounds, Heterocyclic - chemical synthesis Bridged Bicyclo Compounds, Heterocyclic - chemistry Bridged Bicyclo Compounds, Heterocyclic - pharmacology Cyclopropylamines Drug Evaluation, Preclinical Enzyme Inhibitors - chemical synthesis Enzyme Inhibitors - chemistry Enzyme Inhibitors - pharmacology General and cellular metabolism. Vitamins Glucosidase inhibitors Glucosidases - antagonists & inhibitors Medical sciences Molecular Conformation Oxabicyclo[4.1.0] heptanes Pharmacology. Drug treatments Structure-Activity Relationship
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Zusammenfassung:	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 α-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.
ISSN:	0960-894X 1464-3405
DOI:	10.1016/j.bmcl.2009.10.022