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Synthesis of 1,1-[1-Naphthyloxy-2-thiophenyl]-2-methylaminomethylcyclopropanes and Their Evaluation as Inhibitors of Serotonin, Norepinephrine, and Dopamine Transporters

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journal contribution
posted on 08.10.2009, 00:00 by James D. White, Rajan Juniku, Kun Huang, Jongtae Yang, David T. Wong
Stereodefined trisubstituted cyclopropanes bearing naphthyloxy, thiophenyl, and (N-methylamino)methyl groups were synthesized in enantiopure form employing asymmetric cyclopropanation of (E)- and (Z)-allylic alcohols as the key step. In vitro assays of the synthesized cyclopropanes revealed that the Ki of one of the enantiomers as a dual inhibitor of serotonin and norepinephrine transporters is in the low nanomolar range and is comparable to that of duloxetine.