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Synthesis of Carbazolequinone Derivatives as Inhibitors of Toxoplasma gondii Purine Nucleoside Phosphorylase
Author(s) -
Bouaziz Zouhair,
Ghérardi Arnaud,
Régnier François,
Sarciron MarieElizabeth,
Bertheau Xavier,
Fenet Bernard,
Walchshofer Nadia,
Fillion Houda
Publication year - 2002
Publication title -
european journal of organic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 1434-193X
DOI - 10.1002/1099-0690(200206)2002:11<1834::aid-ejoc1834>3.0.co;2-k
Subject(s) - chemistry , purine nucleoside phosphorylase , purine , toxoplasma gondii , stereochemistry , strain (injury) , ether , nucleoside , enzyme , biochemistry , organic chemistry , medicine , antibody , immunology , biology
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)