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Synthesis and pharmacology of 6-substituted benztropines: discovery of novel dopamine uptake inhibitors possessing low binding affinity to the dopamine transporter

  • Autori: Simoni, D.; Rossi, M.; Bertolasi, V.; Roberti, M.; Pizzirani, D.; Rondanin, R.; Baruchello, R.; Invidiata, F.; Tolomeo, M.; Grimaudo, S.; Merighi, S.; Varani, K.; Gessi, S.; Borea, P.; Marino, S.; Cavallini, S.; Bianchi, C.; Siniscalchi, A.
  • Anno di pubblicazione: 2005
  • Tipologia: Articolo in rivista (Articolo in rivista)
  • Parole Chiave: Dopamine Plasma Membrane Transport Proteins; Cocaine; triple reuptake
  • OA Link:


A series of 6α- and 6β-substituted benztropines were synthesized. A marked enantioselectivity was observed for the 6β-methoxylated benztropines, the (1R)-isomers being more potent than the corresponding (1S) compounds. The racemic 6α-methoxy-3-(4′,4″- difluorodiphenylmethoxy)-tropane (5g) was the most potent compound. It has been found that modifications at the 6-position of benztropine might reduce the DAT binding affinity, maintaining otherwise a significant dopamine uptake inhibitory activity. A reinvestigation of the absolute configuration of 6β-methoxytropinone proved the 6R configuration for the (+)-enantiomer.