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  • Title: Imidazo- and triazoloquinolones as antibacterial agents. Synthesis and structure-activity relationships.
    Author: Fujita M, Egawa H, Kataoka M, Miyamoto T, Nakano J, Matsumoto J.
    Journal: Chem Pharm Bull (Tokyo); 1995 Dec; 43(12):2123-32. PubMed ID: 8582014.
    Abstract:
    4,5-Disubstituted 6-cyclopropyl-6,9-dihydro-9-oxo-1H-imidazo (30-32) and triazolo[4,5-f]quinoline-8-carboxylic acids (33-35) were synthesized starting from 5,6-diaminoquinolones 25. The imidazoquinolones 30-32 were equal or superior to the corresponding triazoloquinolone analogues 33-35 in in vitro antibacterial activity. As for the C-5 substituents, a fluorine atom was the most favorable of the three groups, H, F, and Cl. Among the compounds prepared, 4-(cyclic amino)-5-fluoro-imidazoquinolones 31 a-d showed potent and well-balanced antibacterial activity against both gram-positive and gram-negative bacteria. Structure-activity relationships for the C-4 substituents (cyclic amino groups) were also examined in detail.
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