Bioorganic & Medicinal Chemistry Letters 2006-01-01

Synthesis and monoamine transporter affinity of new 2beta-carbomethoxy-3beta-[aryl or heteroaryl]phenyltropanes.

Gilles Tamagnan, David Alagille, Xing Fu, Nora S Kula, Ross J Baldessarini, Robert B Innis, Ronald M Baldwin

Index: Bioorg. Med. Chem. Lett. 16(1) , 217-20, (2006)

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Abstract

A series of 16 new 2beta-carbomethoxy-3beta-[aryl or heteroaryl]phenyltropane derivatives was synthesized and evaluated for binding to monoamine transporters. Most of the compounds exhibited nanomolar affinity for the serotonin transporter (SERT). Four compounds presented a particularly attractive pharmacological profile, with very high SERT affinity (K(i) 0.15-0.5 nM) and selectivity versus the dopamine transporter of 25- to 77-fold.