Chromenylchalcones with inhibitory effects on monoamine oxidase B

Bioorg Med Chem. 2013 Dec 15;21(24):7890-7. doi: 10.1016/j.bmc.2013.10.004. Epub 2013 Oct 16.


Structure-activity relationship (SAR) calculations were used to find monoamine oxidase-B (MAO-B) inhibitors by identifying pharmacophores exhibiting high inhibitory activities. Several such chromenylchalcones were designed and synthesized accordingly. Their inhibitory effects on MAO-B were determined using an HPLC-based method and an MAO-B enzyme assay kit. (E)-3-(6-Methoxy-2H-chromen-3-yl)-1-(2-methoxyphenyl)prop-2-en-1-one exhibited a half-maximal inhibitory concentration of 320 nM. Its molecular-level binding mode with the three-dimensional structure of MAO-B was elucidated using an in silico docking study. The chromenylchalcone scaffold, which is derived from natural products including isoflavonoids and chalcones, had not been previously reported as an MAO-B inhibitor.

Keywords: Chromenylchalcone; Flavonoid; In silico docking; Monoamine oxidase B.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Benzopyrans / chemistry
  • Benzopyrans / pharmacology*
  • Chalcones / chemistry
  • Chalcones / pharmacology*
  • Dose-Response Relationship, Drug
  • Humans
  • Models, Molecular
  • Molecular Structure
  • Monoamine Oxidase / chemistry
  • Monoamine Oxidase / metabolism*
  • Monoamine Oxidase Inhibitors / chemistry
  • Monoamine Oxidase Inhibitors / pharmacology*
  • Structure-Activity Relationship


  • 1-(5-hydroxy-2,2-dimethyl-2H-chromen-6-yl)-3-(2,3,4-trimethoxyphenyl)prop-2-en-1-one
  • Benzopyrans
  • Chalcones
  • Monoamine Oxidase Inhibitors
  • Monoamine Oxidase