87075-33-0Relevant academic research and scientific papers
Synthesis of 4'-Hydroxypropranolol Sulfate, a Major Non-β-Blocking Propranolol Metabolite in Man
Oatis, John E.,Walle, T.,Daniell, H. B.,Gaffney, T. E.,Knapp, D. R.
, p. 822 - 824 (2007/10/02)
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 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.
