| Abstract
| - 2β,3β-Diphenyl-(5),2α,3α-diphenyl-(6), and 2α,3β-diphenyltropane(3) as well as 2,3-diphenyltrop-2-ene (4) were prepared in racemic form and assayedfor inhibition of radioligand bindingat the dopamine (DA), serotonin (5-HT), and norepinephrine (NE)transporters. Among allthree transporters, compounds 4−6 bound the DAtransporter with the highest affinity. The2β,3β-diphenyltropane (5) bound the DA transporter withan IC50 value (28 nM) almost identicalto that of 3β-phenyltropane-2β-carboxylic acid methyl ester (WIN35,065-2) and has muchgreater selectivity relative to binding to the serotonin transporter.A comparison of theradioligand data from this study to radioligand data obtained on otherWIN 35,065-2 analogssuggests that hydrophobicity of the C-2 substituent of some analogs ofthe WIN 35,065-2 classmay be an important contributing factor to binding at the DAtransporter.
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