(Acyloxy) alkyl carbamates as novel bioreversible prodrugs for amines: increased permeation through biological membranes

J Alexander, R Cargill, SR Michelson…

Index: Alexander, Jose; Cargill, Robyn; Michelson, Stuart R.; Schwam, Harvey Journal of Medicinal Chemistry, 1988 , vol. 31, # 2 p. 318 - 322

Full Text: HTML

Citation Number: 68

Abstract

(Acy1oxy) alkyl carbamates of the type R1RzN-CO-O-CHR3-OCO-R4 are described as novel bioreversible prodrugs for primary and secondary amines. These were prepared either by a one-step reaction involving nucleophilic attack on p-nitrophenyl a-(acy1oxy) alkyl carbonates with displacement of p-nitrophenol or by reaction of a-haloalkyl carbamates with silver or mercury salts of carboxylic acids. Enzymatic hydrolysis of the ester bond in these ...