Electrochemistry of potentially bioreductive alkylating quinones : Part 1. Electrochemical properties of relatively simple quinones,as model compounds of mitomycin- and aziridinylquinone-type antitumour agents |
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Authors: | R.J. Driebergen J. Den Hartigh J.J.M. Holthuis A. Hulshoff W.J. van Oort S.J. Postma Kelder W. Verboom D.N. Reinhoudt M. Bos W.E. van der Linden |
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Affiliation: | Department of Chemical Pharmacy, University of Utrecht, Catharijnesingel 60, 3511 GH Utrecht The Netherlands;Department of Chemical Technology, University of Twente, P.O. Box 217, 7500 AE Enschede The Netherlands |
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Abstract: | The influence of methyl-, hydroxy and amino substituents on the electrochemical behaviour of simple 1,4-naphtho-and 1,4-benzoquinones, model compounds of many quinoid antitumour agents, in aqueous media was studied. Significant changes in electrochemical behaviour were observed, potentially the result of a change in the electron density of the quinone moiety, pre- or post-protonation of substituents, hydrogen bond formation, tautomerization reactions and steric interactions between the quinone moiety and substituents. The information obtained was of benefit in the elucidation of the reduction mechanisms of quinoid antitumour agents such as aziridnylquinones and mitomycins. |
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