Synthesis and monoamine transporter affinity of 3-aryl substituted trop-2-enes.
A series of new 3-aryl-tropanes have been synthesized, and their affinities and selectivities were evaluated for monoamine transporters. (1RS)-3-(Fluoren-2-yl)-8-methyl-8-azabicyclo[3.2.1]oct-2-ene exhibited the highest affinity for the human serotonin transporter (IC(50)=14.5nM). It is also 52-fold and 230-fold selective over human dopamine and norepinephrine transporters, respectively.
Krunic
Aleksej
A
Department of Biopharmaceutical Sciences, College of Pharmacy MC 865, University of Illinois at Chicago, 833 S. Wood Street, Rm 335, Chicago, IL 60612-7231, USA.
Mariappan
S V Santhana
SV
Reith
Marteen E A
ME
Dunn
William J
WJ
D050483:Dopamine Plasma Membrane Transport Proteins / Q000378:metabolism*; D006801:Humans; D007700:Kinetics; D008024:Ligands; D008958:Models, Molecular; D009284:Naphthols / Q000138:chemical synthesis / Q000493:pharmacokinetics; D050484:Norepinephrine Plasma Membrane Transport Proteins / Q000378:metabolism*; D014326:Tropanes / Q000138:chemical synthesis* / Q000493:pharmacokinetics; D050493:Vesicular Monoamine Transport Proteins / Q000378:metabolism*
D050483:Dopamine Plasma Membrane Transport Proteins; D008024:Ligands; D009284:Naphthols; D050484:Norepinephrine Plasma Membrane Transport Proteins; D014326:Tropanes; D050493:Vesicular Monoamine Transport Proteins