Synthesis of polyhydroxy 7- and N-alkyl-azepanes as potent glycosidase inhibitors

Tzenge Lien Shih*, Ming Tsung Liang, Kuen Da Wu, Chun Hung Lin

*Corresponding author for this work

Research output: Contribution to journalJournal Article peer-review

16 Scopus citations

Abstract

An effective synthetic method for polyhydroxylated azepanes that contain an alkyl group (Me or Bu) at either the 7- or N-positions is developed. The synthetic routes are accomplished in eight to ten steps from d-(-)-quinic acid. Among the compounds synthesized, the polyhydroxy 7-butyl azepane (compound 3), which possessed the R-configuration at C-7 position, is shown to give potent inhibition against β-galactosidase (IC50 = 3 μM). Preliminary biological data indicate that the length of alkyl groups along with the proper stereochemistry at the C-7 position is essential for acquiring extra binding affinity. Using similar synthetic routes, the polyhydroxy N-methyl and N-butyl azepanes are synthesized for the comparison of their biological activities.

Original languageEnglish
Pages (from-to)183-190
Number of pages8
JournalCarbohydrate Research
Volume346
Issue number2
DOIs
StatePublished - 01 02 2011
Externally publishedYes

Keywords

  • Azepane
  • Glycosidase inhibitor
  • d-(-)-Quinic acid
  • β-Galactosidase

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