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The Structure of Diastereomeric Oxaprotiline Metabolites. An NMR Study
Author(s) -
Winkler Tammo,
Dieterle Walter,
Hung Paul,
Rihs Grety,
Kriemler HansPeter
Publication year - 1984
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.19840670809
Subject(s) - chemistry , diastereomer , stereochemistry , metabolite , biochemistry
The structure of phenolic metabolites of oxaprotiline, obtained from a study with rats and dogs, are assigned with NMR‐spectroscopic methods in combination with MS data and an X‐ray structure analysis of synthetic (9 R *,2′ S *)‐2‐chlorooxaprotiline, the metabolites are shown to be (9 R *,2′ R *)‐2‐hydroxy, 3‐hydroxy‐, and 2‐hydroxy‐3‐methoxyoxaprotiline, and (9 R *,2′ S *)‐2‐hydroxy‐, 3‐hydroxy‐, and 3‐hydroxy‐2‐methoxyoxaprotiline, as well as 2,6‐dihydroxyoxaprotiline.