A new series of 3-phenylcoumarins as potent and selective MAO-B inhibitors.
6-Methyl-3-phenylcoumarins 3-6 were designed, synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. The synthesis of these new compounds (resveratrol-coumarin hybrids) was carried out with good yield by a Perkin reaction, from the 5-methylsalicylaldehyde and the corresponding phenylacetic acid. They show high selectivity to the MAO-B isoenzyme, with IC(50) values in the nanomolar range. Compound 5 is the most active compound and is several times more potent and selective than the reference compound, R-(-)-deprenyl.
Departamento de Química Orgánica, Facultad de Farmacia, 15782 Santiago de Compostela, Spain. mariacmatos@gmail.com
Maria Joao
MJ
Matos
Dolores
D
Viña
Elias
E
Quezada
Carmen
C
Picciau
Giovanna
G
Delogu
Francisco
F
Orallo
Lourdes
L
Santana
Eugenio
E
Uriarte
D000975:Antioxidants; D003374:Coumarins / Q000138:chemical synthesis / Q000737:chemistry* / Q000494:pharmacology*; D015195:Drug Design; D006801:Humans; D020128:Inhibitory Concentration 50; D008995:Monoamine Oxidase / Q000187:drug effects; D008996:Monoamine Oxidase Inhibitors / Q000138:chemical synthesis / Q000737:chemistry*; D000077185:Resveratrol; D012642:Selegiline / Q000494:pharmacology; D013267:Stilbenes / Q000737:chemistry*; D013329:Structure-Activity Relationship
D000975:Antioxidants; D003374:Coumarins; D008996:Monoamine Oxidase Inhibitors; D013267:Stilbenes; D012642:Selegiline; D008995:Monoamine Oxidase; D000077185:Resveratrol