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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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Published in: | Bioorganic & medicinal chemistry letters 2004-02, Vol.14 (3), p.585-589 |
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Main Authors: | , , , , , , |
Format: | Article |
Language: | English |
Subjects: | |
Citations: | Items that this one cites Items that cite this one |
Online Access: | Get full text |
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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. |
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ISSN: | 0960-894X 1464-3405 |
DOI: | 10.1016/j.bmcl.2003.11.064 |