Synthesis of 6.alpha.-methyldigitoxigenin 3-acetate

In order to determine the influence of a 6alpha-methyl group activity, the 6alpha-methyl derivative of digitoxigenin 3-acetate 14 was prepared and pharmacologically tested in comparison with digitoxigenen 3-acetate. The synthesis of 6alpha-methyldigitoxigenin 3-acetate (14) was performed starting fr...

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Bibliographic Details
Published in:Journal of medicinal chemistry 1975-12, Vol.18 (12), p.1258-1261
Main Authors: Valcavi, Umberto, Corsi, Bruno, Caponi, Roberto, Innocenti, Sergio, Martelli, Paola
Format: Article
Language:English
Subjects:
Animals
Cardanolides - chemical synthesis
Cats
Digitoxigenin - analogs & derivatives
Digitoxigenin - chemical synthesis
Digitoxigenin - pharmacology
Guinea Pigs
In Vitro Techniques
Molecular Conformation
Myocardial Contraction - drug effects
Stimulation, Chemical
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Summary:In order to determine the influence of a 6alpha-methyl group activity, the 6alpha-methyl derivative of digitoxigenin 3-acetate 14 was prepared and pharmacologically tested in comparison with digitoxigenen 3-acetate. The synthesis of 6alpha-methyldigitoxigenin 3-acetate (14) was performed starting from 21-hydroxy-4-pregnene-3,20-dione (1). According to the cardiac activity determined on guinea-pig isolated heart and by slow infusion in the cat, the 6alpha-methyldigitoxigenin 3-acetate (14) is not more active than digitoxigenin 3-acetate.
ISSN:0022-2623
1520-4804
DOI:10.1021/jm00246a020