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KMID : 0617319940040010072
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Journal of Pharmacetical Sceiences Ewha Womans University
1994 Volume.4 No. 1 p.72 ~ p.77
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The Synthesis of 6-(N-Arylamino)-7-Chloro-5,8-Quinolinedione Derivatives for Evaluation of Antifungal Activities
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Ryu Chung-Kyu
Kim Hee-Jeong
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Abstract
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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 KCIO_3 in HCI to give 6,7-dichloro-5,8-quinolinediones (Ⅲ). 6-(N-Arylamino)-7-chloro-5,8-quinolinediones 1-12 were prepared by regioselective nucleophilic substitution of Ⅲ with arylamines. In the presence of CeCl_3, the N-aiylamino groups were introduced at the 6-position of 5,8-quinolinedione ring by the regioselective substitution. These derivatives 1-12 were tested for antifungal and also antibacterial activities, in vitro, against Candida albicans, Aspergillus niger, Tricophyton mentagrophytes, Bacillus subtilis, Pseudomonas aeruginosa, Staphylococcus aureus and Escherichia 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 and 9 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 and 7 showed the very potent antifungal activities. 1 was the most effective in preventing the growth of Candida albicans, Aspergillus niger, Tricophyton mentagrophytes, Bacillus subtilis and Staphylococcus aureus at MIC 1.6 ㎍/㎖.
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