Abstract
9-Ethyl-6-hydroxycarbazolequinone (9) was synthesized and submitted to a hetero Diels−Alder reaction towards azadienes 10a or 10b to afford the hydroxypyridocarbazole-5,11-diones 11 or 12a,b. A Bracher cyclization applied to compound 12b led to the 9-hydroxyquinoneimine 15 admixed with its 9-methyl ether 16. These compounds as well as other carbazolequinone derivatives were evaluated towards a purine nucleoside phosphorylase isolated from two strains of Toxoplasma gondii (a virulent strain RH and a cystic strain ME 49). The carbazolequinones 1a, 1b, 1d, 9 and pyridocarbazolequinones 2a, 4 and 5 have shown inhibitory activities similar or better than those observed with the reference compound 8-aminoguanosine. (© Wiley-VCH Verlag GmbH, 69451 Weinheim, Germany, 2002)
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