title: Selected furanochalcones as inhibitors of monoamine oxidase.
abstract: The validity of the chalcone scaffold for the design of inhibitors of monoamine oxidase has previously been illustrated. In a systematic attempt to investigate the effect of heterocyclic substitution on the monoamine oxidase inhibitory properties of this versatile scaffold, a series of furanochalcones were synthesized. The results demonstrate that these furan substituted phenylpropenones exhibited moderate to good inhibitory activities towards MAO-B, but showed weak or no inhibition of the MAO-A enzyme. The most active compound, 2E-3-(5-chlorofuran-2-yl)-1-(3-chlorophenyl)prop-2-en-1-one, exhibited an IC50 value of 0.174 μM for the inhibition of MAO-B and 28.6 μM for the inhibition of MAO-A. Interestingly, contrary to data previously reported for chalcones, these furan substituted derivatives acted as reversible inhibitors, while kinetic analysis revealed a competitive mode of binding.
authors.affiliation: Pharmaceutical Chemistry, School of Pharmacy, North-West University, Private Bag X6001, Potchefstroom 2520, South Africa.
authors.forename: Sarel J
authors.initials: SJ
authors.lastname: Robinson
authors.forename: Jacobus P
authors.initials: JP
authors.lastname: Petzer
authors.forename: Anél
authors.initials: A
authors.lastname: Petzer
authors.forename: Jacobus J
authors.initials: JJ
authors.lastname: Bergh
authors.forename: Anna C U
authors.initials: AC
authors.lastname: Lourens
mesh_terms: D047188:Chalcones / Q000737:chemistry* / Q000494:pharmacology*; D005663:Furans / Q000737:chemistry / Q000494:pharmacology; D006801:Humans; D008995:Monoamine Oxidase / Q000378:metabolism; D008996:Monoamine Oxidase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D011994:Recombinant Proteins / Q000378:metabolism
chemical_list: D047188:Chalcones; D005663:Furans; D008996:Monoamine Oxidase Inhibitors; D011994:Recombinant Proteins; D008995:Monoamine Oxidase
keywords: Chalcone; Competitive; MAO-B; Monoamine oxidase; Reversible inhibition