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Synthesis of deuterated optically active verapamil and gallopamil, and of N ‐ 13 C‐methyl‐verapamil
Author(s) -
Theodore Louis J.,
Nelson Wendel L.
Publication year - 1987
Publication title -
journal of labelled compounds and radiopharmaceuticals
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.432
H-Index - 47
eISSN - 1099-1344
pISSN - 0362-4803
DOI - 10.1002/jlcr.2580241007
Subject(s) - chemistry , gallopamil , verapamil , isopropyl , moiety , deuterium , ring (chemistry) , stereochemistry , medicinal chemistry , alkyl , methyl group , pyridazine , calcium , organic chemistry , physics , quantum mechanics
Deuterated (‐)‐verapamil, (2S)‐(‐)‐2‐(2,5,6‐ 2 H 3 ‐3,4‐dimethoxyphenyl)‐2‐isopropyl‐5‐[(2,5,6‐ 2 H 3 ‐3,4‐dimethoxyphenethyl)methylamino]valeronitrile, and its analog (‐)‐ 2 H 5 ‐gallopamil, (2S)‐(‐)‐2‐(2,6‐ 2 H 2 ‐3,4,5‐trimethoxyphenyl)‐2‐isopropyl‐5‐[(2,5,6‐ 2 H 3 ‐3,4‐dimethoxyphenethyl)methylamino]valeronitrile, were prepared. (‐)‐Gallopamil readily incorporated five atoms of deuterium into the available positions in the aromatic rings. (‐)‐ 2 H 6 ‐Verapamil was prepared from ring trideuterated 3,4‐dimethoxyphenylacetic acid and (2S)‐(+)‐triphenyl‐methoxy‐2‐[(methanesulfonyl)oxy]propane. Three additional atoms of deuterium were incorporated into the aromatic ring of the N ‐methyl‐3,4‐dimethoxyphenethylamine moiety incorporated as the the short N ‐alkyl side chain. N ‐ 13 C‐Methylverapamil was prepared from N ‐ 13 C‐methyl‐3,4‐dimethoxyphenethylamine.