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- Title
Synthesis of rel-(3 RS,3a SR,7a SR)-3-(4-Chlorophenyl)-3a,4,5,6,7,7a-hexahydro-1-methylindolin-6-one, the Main Metabolite of the Analgesic Ro 15-8081: A Potent Amine-Uptake Inhibitor.
- Authors
Bös, Michael; Burkard, Willy P.; Moreau, Jean-Luc; Schönholzer, Peter
- Abstract
The synthesis of the title compound 2 and its diastereoisomer 3 was accomplished using tricarbonyl[1-5- n-(4-methoxycyclohexa-2,4-dien-1-yl)]iron tetrafluoroborate ( 4) as a precursor to the cyclohexanone ring. The assignments of the relative configurations of 2 and 3 are based on the X-ray analysis of compound 3. Both compounds 2 and 3 are potent inhibitors of neuronal noradrenaline uptake in rats with similar potencies in vitro as compared to amitriptyline and desipramine. Compounds 2 and 3 are less potent as serotonin-uptake inhibitors, very weak inhibitors of dopamine uptake, and virtually devoid of antinociceptive activity.
- Publication
Helvetica Chimica Acta, 1990, Vol 73, Issue 4, p932
- ISSN
0018-019X
- Publication type
Article
- DOI
10.1002/hlca.19900730421