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EnglishA 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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| Data di pubblicazione: | 2005 | |
| Titolo: | Synthesis and pharmacology of 6-substituted benztropines: Discovery of novel dopamine uptake inhibitors possessing low binding affinity to the dopamine transporter | |
| Autori: | 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 | |
| Rivista: | JOURNAL OF MEDICINAL CHEMISTRY | |
| Abstract: | 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. | |
| Handle: | http://hdl.handle.net/11392/1198100 | |
| Appare nelle tipologie: | 03.1 Articolo su rivista |
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