RGD Reference Report - Synthesis and pharmacology of 6-substituted benztropines: discovery of novel dopamine uptake inhibitors possessing low binding affinity to the dopamine transporter. - Rat Genome Database

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Synthesis and pharmacology of 6-substituted benztropines: discovery of novel dopamine uptake inhibitors possessing low binding affinity to the dopamine transporter.

Authors: Simoni, D  Rossi, M  Bertolasi, V  Roberti, M  Pizzirani, D  Rondanin, R  Baruchello, R  Invidiata, FP  Tolomeo, M  Grimaudo, S  Merighi, S  Varani, K  Gessi, S  Borea, PA  Marino, S  Cavallini, S  Bianchi, C  Siniscalchi, A 
Citation: Simoni D, etal., J Med Chem. 2005 May 5;48(9):3337-43.
RGD ID: 1625660
Pubmed: PMID:15857139   (View Abstract at PubMed)
DOI: DOI:10.1021/jm0490235   (Journal Full-text)

A series of 6alpha- and 6beta-substituted benztropines were synthesized. A marked enantioselectivity was observed for the 6beta-methoxylated benztropines, the (1R)-isomers being more potent than the corresponding (1S) compounds. The racemic 6alpha-methoxy-3-(4',4' '-difluorodiphenylmethoxy)tropane (5 g) was the most potent compound. It has been found that modifications at the 6-position of benztropine might reduce the DAT binding affinity, maintaining otherwise a significant dopamine uptake inhibitory activity. A reinvestigation of the absolute configuration of 6beta-methoxytropinone proved the 6R configuration for the (+)-enantiomer.

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Gene Slc6a3 solute carrier family 6 member 3 Rattus norvegicus

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