Synthesis of 4'- and 5'-hydroxyoxprenolol: pharmacologically active ring-hydroxylated metabolites of oxprenolol

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Abstract
Synthesis and preliminary pharmacological activity data for 4''- and 5''-hydroxyoxprenolol are reported. The synthetic routes make use of the isomeric 2-pyranyl monoether derivatives of 4-hydroxysalicylaldehyde and 2,5-dihydroxyacetophenone. The corresponding O-allyl ethers were converted to substituted phenols by Baeyer-Villiger oxidation and the propanolamine side chain elaborated using epichlorohydrin, followed by oxirane ring opening with isopropylamine. Each hydroxylated metabolite is .apprx. 10 times less potent than oxprenolol as an antagonist to the isoproterenol-induced relaxation of guinea pig tracheal strips.