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Preparation of radio labeled 3 alpha hydroxy 7 keto 5 beta cholanic acid and its glycine and taurine conjugates

Journal of Labelled Compounds & Radiopharmaceuticals 16(3): 421-434

Preparation of radio labeled 3 alpha hydroxy 7 keto 5 beta cholanic acid and its glycine and taurine conjugates

3.alpha.-Hydroxy-7-keto-5.beta.-cholanic acid was prepared from cholic acid by a route which allowed introduction of 3H into positions 11 and 12 of the steroid C ring. Labeling with 14C was done by halodecarboxylation and resynthesis of the carboxyl function with 14C cyanide. The conjugates of both 3H- and 14C-labeled compounds with glycine and taurine were prepared. 14C-labeled compounds were prepared by degradation of the carboxyl-containing side chain to the norchloride, which was used to prepare the homologous 14C-containing nitrile. Hydrolysis afforded the acid in good yield. 3H was introduced into the C ring of the steroid nucleus by dehydration of 3.alpha.,12.alpha.-dihydroxy-7-keto-5.beta.-cholanic acid to the .DELTA.11-alkene which was catalytically tritiated. Physical and spectral data are presented to characterize the new compounds and TLC methods for purification are reported.

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Accession: 006173766

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