Resolution, EPC-syntheses, absolute stereochemistry, and pharmacology of the (S)-(+)- and (R)-(-)-isomers of the MAO-A inhibitor tetrindole hydrochloride.
Resolution of (RS)-tetrindole (3) and enantioselective reductions of the imine 7 yielded (S)-(+)-(4) and (R)-(-)-tetrindole (5). The absolute stereochemistry of 4 was established by X-ray analysis of the corresponding Mosher amide 6. From in vitro as well as in vivo data (MAO-inhibition, levels of monoamines and their respective metabolites in rat brain), 4 was identified as the eutomer.
D000818:Animals; D001921:Brain / Q000187:drug effects; D002227:Carbazoles / Q000737:chemistry* / Q000494:pharmacology*; D008099:Liver / Q000187:drug effects; D015394:Molecular Structure; D008996:Monoamine Oxidase Inhibitors / Q000737:chemistry* / Q000494:pharmacology*; D051381:Rats; D011919:Rats, Inbred Strains; D013237:Stereoisomerism; D013329:Structure-Activity Relationship
D002227:Carbazoles; D008996:Monoamine Oxidase Inhibitors; C082644:tetrindole