Substituted furans as potent lipoxygenase inhibitors: Synthesis, in vitro and molecular docking studies

Bioorg Chem. 2017 Apr:71:97-101. doi: 10.1016/j.bioorg.2017.01.016. Epub 2017 Jan 24.

Abstract

A number of 2-methyl-4-(2-oxo-2-phenyl-ethyl)-5-phenyl-furan-3-carboxylic acid alkyl ester derivatives (3a-j) were synthesized and evaluated for their in vitro inhibitory activity on soybean lipoxygenase enzyme. Among the screened compounds, 5-(4-bromo-phenyl)-4-[2-(4-bromo-phenyl)-2-oxo-ethyl]-2-methyl-furan-3-carboxylic acid methyl ester (3g) has been found to exhibit potent inhibitory activity with IC5012.8μM using nordihydroguaiaretic acid (NDGA) as standard. Molecular modeling was employed for better understanding of the binding between compounds and soybean lipoxygenase enzyme. The predicted binding energy values correlated well with the observed in vitro data.

Keywords: Anti-inflammatory; Binding energy; Furan-3-carboxylic acid ester; Molecular docking; Soybean lipoxygenase.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Furans / chemistry*
  • Furans / pharmacology*
  • Glycine max / drug effects
  • Glycine max / enzymology*
  • Lipoxygenase / chemistry
  • Lipoxygenase / metabolism*
  • Lipoxygenase Inhibitors / chemistry*
  • Lipoxygenase Inhibitors / pharmacology*
  • Molecular Docking Simulation

Substances

  • Furans
  • Lipoxygenase Inhibitors
  • 2-methylfuran
  • Lipoxygenase