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Chemoenzymatic synthesis and binding affinity of novel ( R)- and ( S)-3-aminomethyl-1-tetralones, potential atypical antipsychotics

A series of ( R)- and ( S)-3-aminomethyl-1-tetralones, conformationally constrained analogues of haloperidol, have been obtained by enzymatic resolution of the corresponding racemic 3-hydroxymethyl-1-tetralones using Pseudomonas fluorescens lipase. Their binding affinities at dopamine D 2 and seroto...

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Bibliographic Details
Published in:Bioorganic & medicinal chemistry letters 2004-02, Vol.14 (3), p.585-589
Main Authors: Caro, Yolanda, Torrado, Marı́a, Masaguer, Christian F., Raviña, Enrique, Padı́n, Fernando, Brea, José, Loza, Marı́a I.
Format: Article
Language:English
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Summary:A series of ( R)- and ( S)-3-aminomethyl-1-tetralones, conformationally constrained analogues of haloperidol, have been obtained by enzymatic resolution of the corresponding racemic 3-hydroxymethyl-1-tetralones using Pseudomonas fluorescens lipase. Their binding affinities at dopamine D 2 and serotonin 5-HT 2A and 5-HT 2C receptors were determined showing in some cases an atypical antipsychotic profile with Meltzer's ratio higher than 1.30. The chemoenzymatic preparation and the binding affinities of new ( R)- and ( S)-3-aminomethyl-1-tetralones is described. Some of these compounds [e.g., ( S)-(+)- 8d] showed potential atypical antipsychotic profiles with Meltzer's ratio higher than 1:30.
ISSN:0960-894X
1464-3405
DOI:10.1016/j.bmcl.2003.11.064