Synthesis and Biological Evaluation of Hyperforin Analogues. Part I. Modification of the Enolized Cyclohexanedione Moiety

Modification of the St. John's wort acylphloroglucinol constituent, hyperforin (<BO>1</BO>), by acylation, alkylation, and oxidation resulted in detrimental effects on the inhibition of the synaptosomal accumulation of serotonin, showing the existence of definite structure−activity relationships in this in vitro test system and highlighting the role of the enolized cyclohexanedione moiety for activity on neurotransmitter reuptake.