Abstract
A series of 6α- and 6β-substituted benztropines were synthesized. A marked enantioselectivity was observed for the 6β-methoxylated benztropines, the (1R)-isomers being more potent than the corresponding (1S) compounds. The racemic 6α-methoxy-3-(4′,4″- difluorodiphenylmethoxy)-tropane (5g) 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 6β-methoxytropinone proved the 6R configuration for the (+)-enantiomer.
Lingua originale | English |
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pagine (da-a) | 3337-3343 |
Numero di pagine | 7 |
Rivista | Journal of Medicinal Chemistry |
Volume | 48 |
Stato di pubblicazione | Published - 2005 |
All Science Journal Classification (ASJC) codes
- Molecular Medicine
- Drug Discovery