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Bioorg Med Chem. 1999 Nov;7(11):2465-71.

Studies on 6-aminoquinolones: synthesis and antibacterial evaluation of 6-amino-8-ethyl- and 6-amino-8-methoxyquinolones.

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Istituto di Chimica e Tecnologia del Farmaco, Università di Perugia, Italy.


From our quantitative structure-activity relationship (QSAR) study on a large set of 6-aminoquinolones, which indicated that a group larger than methyl could be allocated at C-8 position, we have synthesized two new series of 6-aminoquinolones characterized by the presence of an ethyl or a methoxy group at C-8 position. The antibacterial evaluation shows that, while the 8-ethyl derivatives were devoid of any antibacterial activity, the introduction of methoxy group gave compounds with good antibacterial activity, especially against gram-positive bacteria. A tentative explanation of the different behaviours among the 8-substituted analogues is given taking into account both the length and electronic properties of the C-8 groups.

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