A series of compounds, whose structure are analogs to that of commercial antidepressant duloxetine, were designed and prepared by means of a one-pot copper-catalyzed aziridinization and ring opening.. These were modified attaching thiophen-2-yl-methoxy and furan-2-yl-methoxy moieties and employing o-nitrobenzenesulfonyl iminophenyliodinane as both nitrogen source and oxidant. For primary amines, the nosyl group was removed directly from the obtained compounds. In addition, the nitrogen was then sequentially methylated and deprotected to obtain secondary amines. Tertiary amines were obtained using the classical reductive amination (Figure 1). Yields of reactions ranged 50-70%. Figure 1. General structure of compounds synthesized. 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-heteroarylmethoxy-N-phenethylamines as possible monoamine neurotransmitter transporter blockers

2019 Spring National Meeting

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