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Combinatorial approach to N-substituted aminocyclitol libraries by solution-phase parallel synthesis and preliminary evaluation as glucocerebrosidase inhibitors

Academic Article
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Overview

authors

  • Serrano-Navarro, Pedro
  • Casas, J.
  • Zucco, M.
  • Emeric, G.
  • Egido-Gabas, M.
  • Llebaria, A.
  • Delgado, A.

publication date

  • January 2007

journal

  • Journal of Combinatorial Chemistry  Journal

abstract

  • Libraries of N-substituted aminocyclitol derivatives of the scyllo and racemic chiro series by means of parallel solution-phase methodology with the help of robotic technology are described. Chemical diversity has been introduced by reaction of selected scaffolds with a set of aldehydes, acyl chlorides, sulfonyl chlorides, chloroformates, and amines to afford the corresponding amines, amides, sulfonamides, carbamates and ureas, respectively. The optimized methodology has proven excellent, in terms of overall purities of the resulting libraries, for the production of amides. Sulfonamides and carbamates have been obtained in slightly lower purities, while amines afforded modest results. Selected library members have been evaluated as inhibitors of recombinant glucocerebrosidase with K(i) values ranging in the low micromolar scale for the most active members.

subject areas

  • Alcohols
  • Carbamates
  • Combinatorial Chemistry Techniques
  • Cyclohexanes
  • Enzyme Inhibitors
  • Glucosylceramidase
  • Hexosamines
  • Humans
  • Inhibitory Concentration 50
  • Magnetic Resonance Spectroscopy
  • Mass Spectrometry
  • Spectrophotometry, Infrared
  • Sulfonamides
  • Urea
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Identity

International Standard Serial Number (ISSN)

  • 1520-4766

Digital Object Identifier (DOI)

  • 10.1021/cc060080o

PubMed ID

  • 17206831
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Additional Document Info

start page

  • 43

end page

  • 52

volume

  • 9

issue

  • 1

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