Abstract
A series of 6-(N-arylamino)-7-chloro-5,8-quinolinedione derivatives was newly synthesized for the evaluation of antifungal activities. 5-Amino-8-hydroxy-quinoline (II) was treated with KClO3 in HCl to give 6,7-dichloro-5,8-quinolinediones (III). 6-(N-arylamino)-7-chloro-5,8-quinolinediones1–12 were prepared by regioselective nucleophilic substitution of III with arylamines. In the presence of CeCl3, the N-arylamino groups were introduced at the 6-position of 5,8-quinolinedione ring by the regioselective substitution. These derivatives1–12 were tested for antifungal and also antibacterial activities,in vitro, againstCandida albicans, Aspergillus niger, Tricophyton mentagrophytes, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus andEscherichia coli. The MIC values were determined by the two-fold agar/streak dilution method. Newly obtained 6-(N-arylamino)-7-chloro-5,8-quinolinedione derivatives showed potent antifungal and antibacterial activities. Among these derivatives,1, 3, 5, 7, 8 and9 showed more potent antifungal activities than fluconazole and griseofulvin. Also most of derivatives were found to be more active than ampicillin against gram-positive bacteria.1 and7 showed the very potent antifungal activities.1 was the most effective in preventing the growth ofCandida albicans, Aspergillus niger, Tricophyton mentagrophytes, Bacillus subtilis andStaphylococcus aureus at MIC 1.6 μg/ml.
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Ryu, CK., Kim, HJ. The synthesis of 6-(N-Arylamino)-7-chloro-5,8-quinolinedione derivatives for evaluation of antifungal activities. Arch. Pharm. Res. 17, 139–144 (1994). https://doi.org/10.1007/BF02974248
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DOI: https://doi.org/10.1007/BF02974248