Resolution, EPC‐Syntheses, Absolute Stereochemistry, and Pharmacology of the ( S )‐(+)‐ and ( R )‐(—)‐Isomers of the MAO‐A Inhibitor Tetrindole Hydrochloride | Zendy

Bös Michael | Zendy; Canesso Rolf | Zendy; Kettler Rolf | Zendy; Keller Hans H. | Zendy; Schönholzer Peter | Zendy

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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.

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