Metabolic study of 2-(acetyl-imino)-3-[2-hydroxy-2-(2-thienyl)-ethyl]-thiazoline in chickens. Detection of an active metabolite, 5,6-dihydro-6-(2-thienyl)-imidazo[2,1-b]thiazole
✍ Scribed by Fernand T. N. Allewijn; Paul J. A. Demoen
- Publisher
- John Wiley and Sons
- Year
- 1966
- Tongue
- English
- Weight
- 404 KB
- Volume
- 55
- Category
- Article
- ISSN
- 0022-3549
No coin nor oath required. For personal study only.
✦ Synopsis
After oral treatment of chickens with antazonite (R 6438), six basic products have been found by thin-layer chromatography in extracts of feces, one of them being the parent compound. The most important metabolite (metabolite No. 3) was isolated by column chromatography, and its structure was elucidated by physicochemical methods and confirmed by synthesis and analysis. The new product, 5,6-dihydro-6-(2-thienyl)-imidazo[2,1-b]thiazole (antienite, R 8 141) was about 4 times as active as the original compound. There is some evidence suggesting that the anthelmintic activity of R 6438 is due to this metabolite. Two other metabolites were identified by comparison with existing substances o n thin-layer chromatoplates. Further synthetic and parasitological work has shown that chemical modification of R 8141 may result in still more active substances. The most interesting analog, 2,3,5,6tetrahydro-6-phenyl-imidazo[2,1-b] thiazole (tetramisole, R 8299) has been chosen for further detailed parasitological and pharmacological investigation.