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Resolution, EPC‐Syntheses, Absolute Stereochemistry, and Pharmacology of the ( S )‐(+)‐ and ( R )‐(—)‐Isomers of the MAO‐A Inhibitor Tetrindole Hydrochloride
Author(s) -
Bös Michael,
Canesso Rolf,
Kettler Rolf,
Keller Hans H.,
Schönholzer Peter
Publication year - 1995
Publication title -
archiv der pharmazie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.468
H-Index - 61
eISSN - 1521-4184
pISSN - 0365-6233
DOI - 10.1002/ardp.19953280710
Subject(s) - chemistry , stereochemistry , amide , absolute configuration , in vivo , hydrochloride , imine , enantioselective synthesis , resolution (logic) , enantiomer , stereoisomerism , molecule , organic chemistry , microbiology and biotechnology , biology , catalysis , artificial intelligence , computer science
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‐inhibiton, levels of monoamines and their respective metabolites in rat brain), 4 was identified as the eutomer.