Selective and potent monoamine oxidase type B inhibitors: substituted semicarbazones and acylhydrazones of aromatic aldehydes and ketones

Article abstract of DOI:10.1016/0223-5234(96)88258-4

The synthesis and the evaluation of the monoamine oxidase A and B inhibitory activities of 21 new substituted acylhydrazones of various aromatic aldehydes and 4-(benzyloxy)acetophenone, and four substituted semicarbazones of benzaldehyde and 4-(benzyloxy)benzaldehyde, are described.The 4-(benzyloxy)phenyl group contributing to a high lipophilicity led to the most active compounds.One of these, compound 3g (IC50 = 3 nM, MAO A/MAO B selectivity > 33 000), was found to act as a revervible and probably tight-binding inhibitor.The studied acyclic hydrazones and semicarbazones are structurally related to other reversible and potent inhibitors, eg, heterocyclic compounds such as 1,3,4-oxadiazol-2(3H)-one derivatives in which the hydrazono group is intracyclic.Some of these new inhibitors might find use in the symptomatic treatment of neurodegenerative processes.MAO B inhibitor / hydrazone (aromatic acyl-) / semicarbazone (aromatic)