Transformation of quercitols into 4-methylenecyclohex-5-ene-1,2,3-triol derivatives, precursors for the chemical chaperones N-octyl-4-epi-β-valienamine (NOEV) and N-octyl-β-valienamine (NOV)

Bioorg Med Chem Lett. 2011 Dec 1;21(23):7189-92. doi: 10.1016/j.bmcl.2011.09.067. Epub 2011 Sep 24.

Abstract

(+)-proto-Quercitol (1) and (-)-vibo-quercitol (2), both of which could be readily prepared by the bioconversion of myo-inositol, were successfully converted into the corresponding 4-methylenecyclohex-5-ene-1,2,3-triol derivatives. These compounds were demonstrated to be suitable precursors, preserving their configurations, for bioactive carba-aminosugars such as the potent chemical chaperone drug candidates, N-octyl-4-epi-β-valienamine (NOEV, 3) and N-octyl-β-valienamine (NOV, 4).

MeSH terms

  • Aniline Compounds / chemistry
  • Animals
  • Carbohydrate Sequence
  • Cattle
  • Cyclohexanes / chemistry*
  • Ecdysone / analogs & derivatives
  • Ecdysone / chemistry
  • Enzyme Inhibitors / chemistry
  • Hexosamines / chemistry*
  • Inhibitory Concentration 50
  • Inositol / analogs & derivatives*
  • Inositol / chemical synthesis
  • Inositol / chemistry
  • Liver / enzymology
  • Methylene Chloride / chemistry*
  • Molecular Sequence Data
  • Structure-Activity Relationship

Substances

  • Aniline Compounds
  • Cyclohexanes
  • Enzyme Inhibitors
  • Hexosamines
  • N-octyl-beta-valienamine
  • proto-quercitol
  • vibo-quercitol
  • 3,5,14-trihydroxycholest-7-en-6-one
  • Ecdysone
  • Cyclohexane
  • Inositol
  • Methylene Chloride
  • aniline