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Pyrroloquinolones and pyrazoloquinolones as potential antibacterial agents. Synthesis and antibacterial activity

Authors
Journal
European Journal of Medicinal Chemistry
0223-5234
Publisher
Elsevier
Publication Date
Volume
31
Issue
12
Identifiers
DOI: 10.1016/s0223-5234(97)86177-6
Keywords
  • Quinolone
  • 1H-Pyrrolo[2
  • 3-F]Quinolone
  • 2H-Pyrrolo[3
  • 4-F]Quinolone
  • 1H-Pyrazolo[3
  • 4-F]Quinolone
  • Antibacterial Activity

Abstract

Summary 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. 1 H-Pyrrolo[2,3- f]quinolone 17a and 2 H-pyrrolo[3,4- f]quinolone 21a exhibited a potent in vitro antibacterial activity.

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