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Synthesis of carbon 14 labeled and tritium labeled 4 4 nitrophenylaminophenylisothiocyanate go 9333 cgp 4540 amoscanate



Synthesis of carbon 14 labeled and tritium labeled 4 4 nitrophenylaminophenylisothiocyanate go 9333 cgp 4540 amoscanate



Journal of Labelled Compounds and Radiopharmaceuticals 22(4): 313-328



Amoscanate [an antihelminthic antifilarial agent] labeled with 14C on the isothiocyanate carbon atom was prepared in an overall yield of 13% at a specific activity of 4.13 .mu.Ci/mg from potassium [14C]thiocyanate. The 4-nitro[U-14C]phenyl ring labeled compound was synthesized in 20.4% overall yield from [U-14C]aniline at a specific activity of 12.2 .mu.Ci/mg. The corresponding tritiated compound was prepared from 4-amino[2-3H]acetanilide at 112 .mu.Ci/mg. Labeling with tritium in the aromatic ring bearing the isothiocyanate group was achieved by catalyzed halogen-tritium replacement. However, for pharmacokinetic and metabolism studies in experimental animals [rats], the 14C- and 3H-labels associated with the phenylisothiocyanate moiety subsequently proved disadvantageous because of the instability of the labels in vivo.

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