Pyrroloquinolones and pyrazoloquinolones as potential antibacterial agents. Synthesis and antibacterial activity |
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Authors: | M Fujita H Egawa T Miyamoto J Nakano J Matsumoto |
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Affiliation: | aExploratory Research Laboratories, Dainippon Pharmaceutical Company Ltd, Enoki 33-94, Suita, Osaka 564, Japan |
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Abstract: | Diethyl 1-cyclopropyl-5,7,8-trifluoro-1,4-dihydro-4-oxoquinoline-3,6-dicarboxylate 4 as a key-intermediate was synthesized via the Dieckmann reaction. The reaction of 4 with nucleophiles proceeded regioselectively at C-5. Facile cyclization between the C-5 and C-6 side chains of the resulting products gave novel pyrroloquinolones 10 and 12 and pyrazoloquinolones 15. They were converted into a series of cyclic amino-substituted pyrroloquinolones 17–21 and pyrazoloquinolones 22–24, and their in vitro antibacterial activities were tested. 1H-Pyrrolo[2,3-f]quinolone 17a and 2H-pyrrolo[3,4-f]quinolone 21a exhibited a potent in vitro antibacterial activity. |
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Keywords: | quinolone 1H-pyrrolo[2,3-f]quinolone 2H-pyrrolo[3,4-f]quinolone 1H-pyrazolo[3,4-f]quinolone antibacterial activity |
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