Synthesis and chromatographic separation of the glucuronides of R-and S-propranolol

JE Oatis Jr, JP Baker, JR McCarthy…

Index: Oatis, J. E.; Baker, J. P.; McCarthy, J. R.; Knapp, D. R. Journal of Medicinal Chemistry, 1983 , vol. 26, # 12 p. 1687 - 1691

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Citation Number: 18

Abstract

One of the major metabolites of propranolol (Inderal) is the 0-glucuronide. In order to further study its disposition, possible metabolism, and contribution to the antihypertensive effect of propranolol, we have synthesized and separated the two diastereomeric propranolol 0-/3-D- glucuronides (9a, b). These compounds were prepared by reaction of naphthol with epichlorohydrin and treatment of the resulting (2RS)-1'-(2, 3-epoxypropoxy) naphthalene ( ...