Journal of Medicinal Chemistry p. 822 - 824 (1985)
Update date:2022-08-03
Topics:
Oatis, John E.
Walle, T.
Daniell, H. B.
Gaffney, T. E.
Knapp, D. R.
4'-Hydroxypropranolol sulfate (8) was recently identified as a major metabolite of propranolol (Inderal).In order to confirm the structure and to further study disposition and biological activity, he have synthesized 8 with use of 1,4-naphthoquinone (1) as the starting material.Reduction and alkylation with benzyl iodide gave 4-(benzyloxy)naphthol (3).Sulfation and chlorosulfuric acid in N,N-dimethylaniline gave potassium 1-(benzyloxy)-4-naphthol sulfate (4).Catalytic hydrogenation, alkylation with <<<(trifluoromethyl)sulfonyl>oxy>methyl>oxirane (6), and amination in isopropylamine gave 8.Racemic 8 was found to be 100-1000 times less potent than racemic propranolol as a β-adrenergic receptor blocking agent in the dog.
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