Archives of Pharmacal Research

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

  • Published : 2002.12.01
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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

References

  1. 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)
  2. 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) https://doi.org/10.1016/S0966-842X(97)01206-7
  3. 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)
  4. 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) https://doi.org/10.1007/BF02976570
  5. 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
  6. 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) https://doi.org/10.1021/jo00361a014
  7. Pratt, Y. T. and Drake, N. L., Synthesis of 6,7-dichloroquinoline- 5,8- quinone. J. Am. Chem. Soc., 82, 1155-1160 (1960) https://doi.org/10.1021/ja01490a035
  8. 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) https://doi.org/10.1016/0003-9861(78)90093-0
  9. 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) https://doi.org/10.1007/BF02974640
  10. 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) https://doi.org/10.1007/BF02974248
  11. 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) https://doi.org/10.1016/S0960-894X(00)00301-2
  12. Tkacz, J. S. and DiDomenico, B., Antifungals: what's in the pipeline. Curr. Opin. Microbiol., 4(5), 540-545 (2001) https://doi.org/10.1016/S1369-5274(00)00248-4