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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
Author(s) -
Bös Michael,
Burkard Willy P.,
Moreau JeanLuc,
Schönholzer Peter
Publication year - 1990
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/hlca.19900730421
Subject(s) - chemistry , desipramine , stereochemistry , tricyclic , amitriptyline , diastereomer , cyclohexanone , ring (chemistry) , tetrafluoroborate , in vitro , medicinal chemistry , pharmacology , biochemistry , antidepressant , organic chemistry , catalysis , medicine , ionic liquid , hippocampus
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.