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Cytotoxic activities of 6-arylamino-7-halo-5,8-quinolinediones against human tumor cell lines

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Abstract

6-Arylamino-7-halo-5,8-quinolinediones (4a-4k, 5a-5b) were tested forin vitro cytotoxicity against human solid tumor cell lines such as A 549 (non-small cell lung), SK-OV-3 (ovarian), SK-MEL-2 (melanoma), HCT-15 (colon) and XF 498 (CNS) by SRB assay. The arylamino-7-chloro-5,8-quinolinediones4 were also evaluated for cyclin-dependent kinase (CDK2 and CDK4) inhibitory effect. Among them, the 5,8-quinolinediones4a and5a with 7-(4-fluorophenyl)amino group were found to be potent cytotoxic against HCT 15, SKOV-3 and XF 498, and the compounds4f and4i showed inhibitory activities for the CDK4.

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References

  • Boger, D. L., Yasuda, M., Mitscher, L. A., Drake, S. D., Kitos, P. A. and Thomson, S. C., Streptonigrin and lavandamycin partial structure. A probe for the minimum potent pharmacophore of streptonigrin, lavandamycin and synthetic quinoline-5,8-diones.J. Med. Chem., 30, 1918–1928 (1987).

    Article  PubMed  CAS  Google Scholar 

  • Collins, K., Jacks, T. and Pavletich, N. P., The cell cycle and cancer.Proc. Natl. Acad. Sci. USA, 94 2776–2778 (1997).

    Article  PubMed  CAS  Google Scholar 

  • Dunphy, W. G.,Methods in Enzymology; Cell Cycle Control. Academic Press, San Diego, pp 1–205, 1997; Phelps, D. E. and Xiong, Y. Assay for activity of mammalian cyclin D-dependent kinases CDK4 and CDK6, 194–205; Meijer, L. and Kim, S-.H. Chemical inhibitors of cyclin-dependent kinases, 113–128.

    Google Scholar 

  • Jeschke, P., Linder, W., Mueller, N. Harder, A. and Mencke, N., New 6(7)amino-substituted-5,8-quinolinediones to combat endoparasites.Eur. Patent., Appl. EP 519, 290 (Cl. C07D215/38) (1992).

  • Lown, J. W. and Sim, S. K., Studies related to antitumor antibiotics. Synthesis of streptonigrin analogues and their single strand scission of DNA.Can. J. Chem., 54, 2563–2572 (1976).

    Article  CAS  Google Scholar 

  • Rao, K. V. and Beach, J. W., Streptonigrin and related compounds 5. Synthesis and evaluation of some isoquinolin analogues.J. Med. Chem., 34, 1871–1879 (1991).

    Article  PubMed  CAS  Google Scholar 

  • Rao, K. V. and Rock, C. P., Streptonigrin and related compounds. 6. Synthesis and activity of some quinoxaline analogues.J. Heterocycl. Chem., 33, 447–458 (1996).

    Article  CAS  Google Scholar 

  • 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).

    Article  CAS  Google Scholar 

  • Ryu, C. K., Lee, I. K., Jung, S. H. and Lee, C. O., Synthesis and cytotoxic activities 6-chloro-7-arylamino-5,8-isoquinolinediones.Bioorg. Med. Chem. Lett., 9(8), 1075–1080 (1999a).

    Article  PubMed  CAS  Google Scholar 

  • Ryu, C. K., Jung, S. H., Lee, J. A., Kim, H. J., Lee, S. H. and Chung, J. H., 6-Arylamino-5,8-quinolinediones and 7-arylamino-5,8-isoquinolinediones as inhibitors of endothelium-dependent vasorelaxation.Bioorg. Med. Chem. Lett., 9(17), 2466–2472 (1999b).

    Article  Google Scholar 

  • Sausville, E. A., Zahararevitz, D., Gussio, R., Meijer, L., Louarn-Leost, M., Kunick, C., Schultz, R., Lahusen, T., Headlee, D., Stinson, S., Arbuck, S. G. and Senderowicz, A., Cyclin-dependent kinases: Initial approaches to exploit a novel therapeutic target.Pharmacol. Ther., 82 285–292 (1999).

    Article  PubMed  CAS  Google Scholar 

  • Schellhammer, C. W. and Petersen, S., Ueber Derivatives des 5,8-Chinolinchinone.Ann. der Chem., 624, 108–119 (1959).

    CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • 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).

    Article  PubMed  CAS  Google Scholar 

  • Webster, K. R., The therapeutic potential of targeting the cell cycle.Exp. Opin. Invest. Drugs, 7(6), 865–887, (1998).

    Article  CAS  Google Scholar 

  • Yasuda, M. and Boger, D. L., Streptonigrin and lavandamycin partial structure. A probe for the minimum potent pharmacophore of the natural occurring antitumor-anitibiotics.J. Heterocycl. Chem., 24, 1253–1259 (1987).

    CAS  Google Scholar 

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Correspondence to Chung-Kyu Ryu.

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Ryu, CK., Kang, HY., Yi, YJ. et al. Cytotoxic activities of 6-arylamino-7-halo-5,8-quinolinediones against human tumor cell lines. Arch Pharm Res 23, 42–45 (2000). https://doi.org/10.1007/BF02976464

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