Journal
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
Volume 19, Issue 17, Pages 5053-5055Publisher
PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.bmcl.2009.07.039
Keywords
Phenylcoumarins; MAOIs; Monoamino oxidase; Perkin reaction; Coumarin-resveratrol hybrids
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Funding
- Spanish Ministerio de Sanidad y Consumo [PI061457, PI061537]
- Xunta da Galicia [BTF20303PR, PXIB203022PR, CSA019203PR]
- Fondazione Banco Sardegna (Italy)
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A series of 6-methyl-3-phenylcoumarins 3-6 were synthesized and evaluated as monoamine oxidase A and B (MAO-A and MAO-B) inhibitors. A comparative study between the three possible mono methoxy 3-phenyl derivatives and the p-hydroxy analogue is reported. The synthesis of these new resveratrol-coumarin hybrids was carried out by a Perkin reaction between the 5-methylsalicylaldehyde and the corresponding phenylacetic acids. The p-methoxy substituted compound 3 was hydrolyzed to 6 by a traditional reaction with hydriodic acid. The prepared compounds show high selectivity to the MAO-B isoenzyme, some of them with IC(50) values in the low nanomolar range. Compound 4, with the methoxy group in meta position, is the most active of this series, with an IC(50) against MAO-B of 0.80 nM, and is several times more potent and MAO-B selective than the R-(-)-deprenyl (reference compound). (C) 2009 Elsevier Ltd. All rights reserved.
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