Biological activities of 3,4,5-trihydroxypiperidines and their N- and O-derivatives

Kate Prichard, David Campkin, Nicholas O'Brien, Atsushi Kato, George W.J. Fleet, Michela I. Simone*

*Corresponding author for this work

Research output: Contribution to journalReview articlepeer-review

31 Scopus citations

Abstract

3,4,5-Trihydroxypiperidines belong to the family of 1,5-dideoxy-1,5-iminosugar natural products and are structural analogues of pentose monosaccharides in the pyranose form. The biological activities of these apparently structurally simple molecules and their N- and O-alkylated and -arylated derivatives are no less remarkable than their C-6 hydroxymethyl counterparts of the hexoses (such as 1-deoxynojirimycin, DNJ). Their biological profiles indicate that the hydroxymethyl branch is crucial to neither potency nor selectivity, with O-alkylation demonstrated to produce exquisite selectivity extending beyond glycosidase inhibition, to immunosuppressant and antibacterial activities.

Original languageEnglish
Pages (from-to)1171-1197
Number of pages27
JournalChemical Biology and Drug Design
Volume92
Issue number1
DOIs
StatePublished - 2018/07

Keywords

  • anti-bacterial
  • anti-diabetes
  • glycosidase
  • iminosugar
  • immunosuppressant
  • lysosomal disease
  • piperidine

ASJC Scopus subject areas

  • Biochemistry
  • Molecular Medicine
  • Pharmacology
  • Drug Discovery
  • Organic Chemistry

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