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Synthesis of 14 C‐ and 3 H‐labelled 4‐(4‐nitrophenyl)aminophenylisothiocyanate (GO 9333 / CGP 4540; amoscanate
Author(s) -
Anjaneyulu B.,
Maller R. K.,
Nagarajan K.,
Kueng W.,
Wirz B.
Publication year - 1985
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.2580220403
Subject(s) - chemistry , acetanilide , aniline , tritium , yield (engineering) , isothiocyanate , carbon 14 , medicinal chemistry , moiety , ring (chemistry) , potassium thiocyanate , thiocyanate , halogen , radiochemistry , stereochemistry , nuclear chemistry , organic chemistry , materials science , quantum mechanics , nuclear physics , metallurgy , alkyl , physics
Amoscanate labelled with carbon‐14 on the isothiocyanate carbon atom was prepared in an overall yield of 13% at a specific activity of 4.13 μCi/mg from potassium [ 14 C]thiocyanate. The 4‐nitro[U‐ 14 C]phenyl ring labelled compound was synthesized in 20.4% overall yield from [U‐ 14 C]aniline at a specific activity of 12.2 μCi/mg. The corresponding tritiated compound was prepared from 4‐amino[2‐ 3 H]acetanilide at 112 μCi/mg. Labelling with tritium in the aromatic ring bearing the isothiocyanate group was achieved by catalysed halogen‐tritium replacement. However, for pharmacokinetic and metabolism studies in experimental animals, the 14 C‐ and 3 H‐labels associated with the phenylisothiocyanate moiety subsequently proved disadvantageous because of the instability of the labels in vivo.