Synthesis of Chromen-4-One-Oxadiazole Substituted Analogs as Potent β-Glucuronidase Inhibitors

Molecules. 2019 Apr 18;24(8):1528. doi: 10.3390/molecules24081528.

Abstract

Chromen-4-one substituted oxadiazole analogs 1-19 have been synthesized, characterized and evaluated for β-glucuronidase inhibition. All analogs exhibited a variable degree of β-glucuronidase inhibitory activity with IC50 values ranging in between 0.8 ± 0.1-42.3 ± 0.8 μM when compared with the standard d-saccharic acid 1,4 lactone (IC50 = 48.1 ± 1.2 μM). Structure activity relationship has been established for all compounds. Molecular docking studies were performed to predict the binding interaction of the compounds with the active site of enzyme.

Keywords: SAR; chromen-4-one; molecular docking; oxadiazole; synthesis; β-glucuronidase inhibition.

MeSH terms

  • Benzopyrans / chemical synthesis*
  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Glucuronidase / chemistry
  • Glucuronidase / metabolism
  • Glycoproteins / chemical synthesis*
  • Glycoproteins / chemistry
  • Glycoproteins / pharmacology*
  • Inhibitory Concentration 50
  • Ligands
  • Molecular Docking Simulation
  • Oxadiazoles / chemical synthesis*
  • Oxadiazoles / chemistry
  • Oxadiazoles / pharmacology*

Substances

  • Benzopyrans
  • Glycoproteins
  • Ligands
  • Oxadiazoles
  • beta-glucuronidase inhibitor
  • Glucuronidase