Substituent effects on the kinetics of reductively-initiated fragmentation of nitrobenzyl carbamates designed as triggers for bioreductive prodrugs

…, BM Sykes, WA Denny, CJ O'Connor

Index: Hay, Michael P.; Sykes, Bridget M.; Denny, William A.; O'Connor, Charmian J. Journal of the Chemical Society - Perkin Transactions 1, 1999 , # 19 p. 2759 - 2770

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Citation Number: 40

Abstract

4-Nitrobenzyl carbamates are of interest as triggers for bioreductive drugs, particularly in conjunction with the E. coli B nitroreductase, which efficiently reduces them to the corresponding hydroxylamines. These then fragment to release highly toxic amine-based toxins. While many 4-nitrobenzyl carbamate derivatives have been evaluated as bioreductive drugs, there has been no systematic study of substituent effects on the rate of ...