Synthesis and evaluation of 9-deoxy analogues of (-)-thysanone, an inhibitor of HRV 3C protease

Eur J Med Chem. 2014 Nov 24;87:220-7. doi: 10.1016/j.ejmech.2014.09.063. Epub 2014 Sep 22.

Abstract

9-Deoxy analogues of the HRV 3C protease inhibitor (-)-thysanone display better inhibitory properties than the natural product, inferring the C9-OH hinders binding to the enzyme.

Keywords: C–H activation; HRV 3C protease; Inhibitor; Pyranonaphthoquinone; Thysanone.

MeSH terms

  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Chemistry Techniques, Synthetic
  • Cysteine Endopeptidases / metabolism
  • Drug Design*
  • Naphthoquinones / chemical synthesis*
  • Naphthoquinones / chemistry
  • Naphthoquinones / pharmacology*
  • Protease Inhibitors / chemical synthesis*
  • Protease Inhibitors / chemistry
  • Protease Inhibitors / pharmacology*
  • Rhinovirus / enzymology*
  • Viral Proteins / antagonists & inhibitors*
  • Viral Proteins / metabolism

Substances

  • Benzopyrans
  • Naphthoquinones
  • Protease Inhibitors
  • Viral Proteins
  • thysanone
  • Cysteine Endopeptidases
  • 3C proteases