3-(1H-pyrrol-1-yl)-2-oxazolidinones as reversible, highly potent, and selective inhibitors of monoamine oxidase type A

3-(1H-Pyrrol-1-yl)-2-oxazolidinones 1a-i have been synthesized as pyrrole analogues of toloxatone (Humoryl), an antidepressant agent belonging to the 3-phenyl-2-oxazolidinone class, and their monoamine oxidase (MAO) type A and B inhibitory activities have been evaluated. The majority of la-i showed inhibitory activity against the A isoform of the enzyme higher than that exerted against the MAO-B, the sole exception being the (S)-5-aminomethylderivative 1d. (R)-5-Methoxymethyl-3-(1-H-pyrrol-1-yl)-2-oxazolidinone 1b, the most potent among test derivatives, was 78-fold more potent than toloxatone.