Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine

Citation
Sa. Lomenzo et al., Synthesis, dopamine and serotonin transporter binding affinities of novel analogues of meperidine, BIOORG MED, 9(23), 1999, pp. 3273-3276
Citations number
18
Categorie Soggetti
Chemistry & Analysis
Journal title
BIOORGANIC & MEDICINAL CHEMISTRY LETTERS
ISSN journal
0960894X → ACNP
Volume
9
Issue
23
Year of publication
1999
Pages
3273 - 3276
Database
ISI
SICI code
0960-894X(199912)9:23<3273:SDASTB>2.0.ZU;2-D
Abstract
A series of meperidine analogues was synthesized and the binding affinities for the dopamine and serotonin transporters were determined. The substitue nts on the phenyl ring greatly influenced the potency and selectivity of th ese compounds for the transporter binding sites. In general, meperidine (3) and its analogues were more selective for serotonin transporter binding si tes and the eaters 9 were more potent than the corresponding nitriles 8. Th e 3,4-dichloro derivative 9e was the most potent ligand of the series for d opamine transporter binding sites while the 2-naphthyl derivative 9g exhibi ted the most potent binding affinity and was highly selective for serotonin transporter binding sites. (C) 1999 Elsevier Science Ltd. All rights reser ved.