Bicyclo[2.2-1]heptanes as novel triple re-uptake inhibitors for the treatment of depression

A series of substituted naphthyl containing chiral [2.2.1] bicycloheptanes were prepared utilizing asymmetric Diels-Alder chemistry. This paper describes structure-activity relationships in this series. The N-methyl 2-naphthyl analogue (16d) and its desmethyl analogue (17d) are active triple re-uptake inhibitors both in vivo and in vitro. (C) 2003 Elsevier Ltd. All rights reserved.