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Record number 438234
Title The Development of an Aza-C-Glycoside Library Based on a Tandem Staudinger/Aza-Wittig/Ugi Three-Component Reaction
Author(s) Wennekes, T.; Bonger, K.M.; Vogel, K.; Berg, S.A. van den; Strijland, A.; Donker-Koopman, W.E.; Aerts, J.; Marel, A. van der; Overkleeft, H.S.
Source European Journal of Organic Chemistry 2012 (2012)32. - ISSN 1434-193X - p. 6420 - 6454.
DOI https://doi.org/10.1002/ejoc.201200923
Department(s) Laboratory for Organic Chemistry
VLAG
Publication type Refereed Article in a scientific journal
Publication year 2012
Keyword(s) ugi 4-component condensation - gaucher-disease - multicomponent reactions - nonlysosomal glucosylceramidase - functionalized pyrrolidines - pharmacological chaperones - n-butyldeoxynojirimycin - combinatorial libraries - bicyclic scaffolds - storage disorders
Abstract We report the tandem Staudinger/aza-Wittig/Ugi three-component reaction mediated synthesis of a 64-member compound library of aza-C-glycosides. The library is composed of four pyrrolidine and three piperidine scaffolds, onto which a number of functional groups is grafted to form seven sublibraries. Variation in the library is achieved by transformation of two pentoses and a hexose into the corresponding 4-azidopentanal and 5-azidohexanal derivatives as precursors for the Staudinger/aza-Wittig process. Further variation is achieved by using different isocyanides as well as protective- and functional-group manipulations on the fully protected Ugi-3CR intermediates. Preliminary biological evaluation of the compound library revealed several low micromolar inhibitors of human acid glucosylceramidase
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