Archives of Pharmacal Research

The Pharmaceutical Society of Korea (대한약학회)
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Synthesis and Antifungal Activity of 5,8-Quinazolinedione Derivatives Modified at Positions 6 and 7

  • Ryu, Chung-Kyu (College of Pharmacy, Ewha Womans University) ;
  • Shim, Ju-Yeon (College of Pharmacy, Ewha Womans University) ;
  • Yi, You-Jin (College of Pharmacy, Ewha Womans University) ;
  • Choi, Ik Hwa (College of Pharmacy, Ewha Womans University) ;
  • Chae, Mi-Jin (College of Pharmacy, Ewha Womans University) ;
  • Han, Ja-Young (College of Pharmacy, Ewha Womans University) ;
  • Jung , Ok-Jai (College of Pharmacy, Ewha Womans University)
  • Published : 2004.01.01
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Abstract

5,8-Quinazolinediones modified at positions 6 and 7 were synthesized and tested for in vitro antifungal activities against Candida species and Aspergillus niger. Most of 5,8-quinazolinediones 3-5 generally exhibited potent antifungal activity. 6-Arylamino-7-chloro-5,8-quinazolinediones (3) generally showed more potent antifungal activity than 7-arylthio-5,8-quinzolinediones (4) and 6,7-bis-(arylthio)-5,8-quinazolinediones (5).

Keywords

References

  1. Giorgi-Renault, S., Renault, J., Gebel-Servolles, P., Baron, M., Paoletti, C., Cros, S., Bissery, M. C., Lavelle, F., and Atassi, G., Heterocyclic quinones 17. A new in vivo active antineoplastic drug. J. Med, Chem., 34, 38-46 (1991) https://doi.org/10.1021/jm00105a007
  2. Jeschke, P., Linder, W., Mueller, N., and Dehne, H. W., Fungicides based on amino-substituted quinohnequinones. Ger. Offen., DE 4,208,874 (1993); Chem. Abstr., 118, 233893 (1993)
  3. 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)
  4. Melesani, G., Marcolin, F., and Rodighiero, G., Synthesis of 5,8quinazolinedione. J. Med. Chem., 13, 161-162 (1970) https://doi.org/10.1021/jm00295a054
  5. Middleton, R. W. and Parrick, J., Heterocyclic quinones: Patai, S., Rappoport, Z.(Eds), The Chemistry of The Quinonoid Compounds. John Wiley & Sons: London, vol 2, pp 1019-1066 (1988)
  6. Park, H. J., Kim, Y.-S., Kim, J. S., Lee, H.-J., Lee, E.-J., Hwang, H. J., Suh, M.-E., Ryu, C.-K., and Lee, S. K., 6-Arylamino-7-chloro-quinazoline-5,8-diones as novel cytotoxic and DNA toposiomerase inhibitory agents. Bioorg. Med. Chem. Lett., 14, 3385-3388 (2004) https://doi.org/10.1016/j.bmcl.2004.04.094
  7. Renault, J., Giorgi-Renault, S., Baron, M., Mailliet, P., Paoletti, C., Cros, S., Viosin, E., and Renault, J., Heterocyclic quinone 4. A new highly cytotoxic drug: 6,7-bis(1-aziridinyl)-5,8quinazolinedione. J. Med. Chem., 26, 1715-1719 (1983) https://doi.org/10.1021/jm00366a011
  8. Roberts, H., Choo, W. M., Smith, S. C., Marzuki, S., Linnane, A. W, Porter, I. 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. and Kim, H. J., 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
  10. Ryu, C.-K., Shin, K.H., Seo, J. H., and Kim, H. J., 6-Arylamino5,8- quinazolinediones as potent inhibitors of endotheliumdependent vasorelaxation. European J. Med. Chem., 37, 77-82 (2002a) https://doi.org/10.1016/S0223-5234(01)01290-9
  11. Ryu, C.-K., Sun, Y. J., Shim, J.Y., You, H. J., Choi, K.U., and Lee, H., Synthesis and antifungal activities of 6,7-bis-[S(aryl)thio]-5,8-quinolinediones. Arch. Pharm. Res., 25, 784-789 (2002b).
  12. Ryu, C.-K., Yi, Y.-J., Choi, I. H., Chae, M. J., Han, J.-Y, Jung, O.J., and Lee, C.-O., Synthesis and cytotoxic activity of 6(substituted-phenyl)amino-5,8-quinazolinediones. Med. Chem. Res., 13 in press (2004)
  13. Shaikh, I. A., Johnson, F., and Grollman, A P., Structure-activity relationship among simple bicyclic analogues. Rate dependent of DNA degradation on quinone reduction potential. J. Med. Chem., 29, 1329-1340 (1986) https://doi.org/10.1021/jm00158a002
  14. Skehan, P., Storeng, R., Scudiero, D., Monks, A., McMahon, J., Vistica, D., Warren, T. W., Bokesch, H., Kenney, S., and Boyd, M. R., New colorimetric cytotoxicity assay for anticancer-drug screening. J. Natl. Cancer Inst., 82,1107-1112 (1990) https://doi.org/10.1093/jnci/82.13.1107