Synthesis and Antibacterial Evaluation of Model Fluoroquinolone- Benzylidene Barbiturate Hybrids
Kamal Sweidan, Walid Abu Rayyan, Musa Abu Zarga, Mustafa M. El-Abadelah and Hani A. Y. Mohammad
Affiliation: Department of Chemistry, The University of Jordan, Amman 11942, Jordan.
The interaction of 1,3-dimethylbarbituric acid (2) with ethyl 7-chloro-1-cyclopropyl-6-fluoro-8-nitro-4-
oxoquinoline-3-carboxylate (1) in basic medium yielded the respective 7-[5-(1,3-dimethylbarbitutic)]-quinoline hybrid
(3). Substituted 5-bis(thioethyl)methylene barbituric acids (5a,b) underwent cyclocondensation with 7,8-diamino-6-
fluoroquinoline-3-carboxylate (4) to produce the respective fluoroquinolone-benzylidene-barbiturate hybrids (6a,b)
incorporating fused-imidazoline moiety. Saponification of the dimethylated ester (6b) gave the respective acid (7). The
new compounds (3,5-7) show low to moderate antibacterial activity against Staphylococcus aureus and E. coli.
Keywords: Antibacterial activity, barbituric acid, fluoroquinolones, hybrid molecules, solid-state 13C NMR.
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