We designed and prepared a series of β-benzyloxy-<i>N</i>-phenethylamines compounds with potential activity as monoamine transporter uptake inhibitors. The new compounds were based on the structure of an analogue of the commercial antidepressant fluoxetine. These compounds were synthesized using, as the key step, the copper-catalyzed aminooxygenation or aziridinization of styrenes. Taking advantage of this chemical reactivity, we made a new series of compounds varying the aromatic moieties one at a time. See Figure 1. All the new compounds were tested as monoamine neurotransmitter transporter blockers using a fluorescence assay and molecular modeling studies were performed to rationalize possible interactions of our compounds with the different monoamine neurotransmitter transporters.

Synthesis of new β-benzyloxy-<i>N</i>-phenethylamines as biogenic amine neurotransmitter transporter blockers

2019 Spring National Meeting

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Synthesis of new β-benzyloxy-N-phenethylamines as biogenic amine neurotransmitter transporter blockers