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Updated: Oct 5, 2026

Facile Preparation of 4-Substituted Quinazoline Derivatives
Published on: February 15, 2016
2-Nitro and 4-nitro-quinone-methides are not irreversible inhibitors of bovine beta-glucuronidase
M Azoulay1, F Chalard, J P Gesson
1Section de Recherche, UMR 176, CNRS-Institut Curie, 2 Paris, France.
Abstract:
4-Benzylamino-(and 4-chloromethyl)-2-nitro-beta-D-glucuronides (4, 10) and their 2-substituted-4-nitro regioisomers (7, 13) were prepared by glycosidation of the 3-nitro-4-hydroxy- and the 2-hydroxy-5-nitro-benzylic alcohol, respectively, with a glucuronyl donor. Carbonate activation followed by reaction with benzylamine or methanesulfonyl chloride afforded, after complete deprotection, the target molecules 4, 7, 10 and 13. These compounds have been synthesized to determine whether these molecules are (or not) glucuronidase inhibitors. After incubation with bovine liver beta-glucuronidase, none of the cleavage products (the titled quinone-methides) showed to be irreversible inhibitors of this enzyme.
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