Cyclization-activated prodrugs. Basic carbamates of 4-hydroxyanisole

…, JE Schwering, PA Lyle, SJ Smith…

Index: Saari, Walfred S.; Schwering, John E.; Lyle, Paulette A.; Smith, Steven J.; Engelhardt, Edward L. Journal of Medicinal Chemistry, 1990 , vol. 33, # 1 p. 97 - 101

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Citation Number: 109

Abstract

A series of basic carbamates of 4-hydroxyanisole was prepared and evaluated as progenitors of this melanocytotoxic phenol. All of the carbamates were relatively stable at low pH but released 4-hydroxyanisole cleanly at pH 7.4 at rates that were structure dependent. A detailed study of the N-methyl-N-[2-(methylamino) ethyl] carbamate showed that generation of the parent phenol followed first-order kinetics with tll2= 36.3 min at pH ...