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Synthesis and Antifungal Activity of 6,7-Bis-[S-(Aryl)thio]-5,8-Quinolinediones  

Ryu, Chung-Kyu (College of Pharmacy, Ewha Womans University)
Sun, Yang-Jung (College of Pharmacy, Ewha Womans University)
Shim, Ju-Yeon (College of Pharmacy, Ewha Womans University)
You, Hea-Jung (College of Pharmacy, Ewha Womans University)
Choi, Ko-Un (College of Pharmacy, Ewha Womans University)
Lee, Hee-Soon (College of Pharmacy, Chungbuk National University)
Publication Information
Archives of Pharmacal Research / v.25, no.6, 2002 , pp. 795-800 More about this Journal
Abstract
6,7-Bis-[S-(aryl)thio]-5,8-quinolinediones 4 and 5 were synthesized by the substitution of 6,7-dichloro-5,8-quinolinediones with appropriate arylthiols. Their antifungal activity were tested in vitro for their growth inhibitory activities against pathogenic fungi in comparison with flucytosine. The antifungal activities were significantly improved by S-(aryl)thio moieties of the compounds 4 and 5. The all tested compounds 4 and 5 showed generally good activities against C. albicans and A. niger ranging from 0.8 to 25 $\mu\textrm{g}$/ml. Among them, compounds 4d-4h and 5a-5c exhibited also good activities against C. krusei and C. tropicalis. The activities of compounds 4j and 4I were comparable to those of flucytosine against all tested fungi.
Keywords
6,7-Bis-[S-(aryl)thio]-5,8-quinolinediones; Antifungal activity; MIC minimum inhibitory concentration; Candida species; A. niger;
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1 Pratt, Y. T. and Drake, N. L., Synthesis of 6,7-dichloroquinoline- 5,8- quinone. J. Am. Chem. Soc., 82, 1155-1160 (1960)   DOI
2 Roberts, H., Choo, W. M., Smith, S. C., Marzuki, S., Linnane, A. W., Porter, T. H. and Folkers, K., The site of inhibition of mitochondrial electron transfer by coenzyme Q analogs. Arch. Biochem. Biophys., 191, 306-315 (1978)   DOI   ScienceOn
3 Potts, K. T., Bhattacharjee, D. and Walsh, E. B., Cycloaddition routes to azaanthraquinone derivatives. Use of azadieno- phlles, J. Org. Chem., 51, 2011-2021 (1986)   DOI
4 Groll, A. H., De Lucca, A. J. and Walsh. T. J., Emerging targets for the development of novel antifungal therapeutics. Trend Microbiol. 6 (3), 117-124. (1998)   DOI   ScienceOn
5 Ryu, C.-K., Kang, H. Y., Yi, Y. J., Shin, K. H. and Lee, B. H., Synthesis and antifungal activities of 5/6-arylamino-4,7-dioxobenzothiazoles. Bioorg. Med. Chem. Lett., 10(14), 1589-1591 (2000)   DOI   ScienceOn
6 Mcginnis M. R. and Rindali, M. G., Antifungal drug. In Lorian, V.(Eds.), Antibiotics in Laboratory Medicine (4th ed.). Williams and Wilkins, Baltimore, pp. 176-211, 1996
7 Ryu, C.-K, Choi, J. A. and Kim, S. H., Synthesis and antifungal evaluation of 6-(N-arylamino)-7-methylthio-5,8-quinolinediones. Arch. Pharm. Res., 21(4), 440-444 (1998)   DOI   ScienceOn
8 Tkacz, J. S. and DiDomenico, B., Antifungals: what's in the pipeline. Curr. Opin. Microbiol., 4(5), 540-545 (2001)   DOI   ScienceOn
9 Ryu, C.-K. and Kim, H. J., The synthesis of 6-(N-arylamino)-7chloro- 5,8-quinolinedione derivatives for evaluation of antifungal activities. Arch. Pharm. Res., 17(2), 139-144 (1994)   DOI   ScienceOn
10 Jeschke, P., Linder, W., Mueller, N. and Dehne, H. W., Fungicides based on amino-substituted quinolinequinones. Ger. Offen., DE 4,208,874 (1993); Chem. Abstr., 1'8, 233893 (1993)
11 Chang, E.-E., Cheng, H.-H., Lai, J.-E. and Kuo, H.-S., Heteroquinone with biological activity-Synthesis and antimicrobial activity of alkylmercapto-5,8-quinolinediones. Chinese Pharmaceut. J., 47, 531-538 (1995)
12 Lee, H., Lee, J., Hong, S. S., Yang, S. I., Jung, S. H., Jahng, Y. and Cho, J. S., Synthesis and in vitro cytotoxicity of 2-alky-laminosubstituted quinoline derivatives. Arch. Pherm. Res., 23 (5), 450-454 (2000)   DOI   ScienceOn