Synthesis and Cytotoxic Activities of 8-Alkyl or 8-Aryl-8,9-dihydro-7H-isoindolo[5,6-g]quinoxaline-7,9-diones

  • Jung Jae-Kyung (College of Pharmacy, Chungbuk National University) ;
  • Jung Eun-Kyung (College of Pharmacy, Chungbuk National University) ;
  • Kwon Nam-Goong (College of Pharmacy, Chungbuk National University) ;
  • Cho Jung-Sook (College of Medicine, Dongguk University) ;
  • Kim Hwan-Mook (Korea Research Institute of Bioscience and Biotechnology) ;
  • Park Sung-Gyu (Korea Research Institute of Bioscience and Biotechnology) ;
  • Yoo Yeong-Ah (Korea Research Institute of Bioscience and Biotechnology) ;
  • Kwon Joo-Hee (Korea Research Institute of Bioscience and Biotechnology) ;
  • Lee Hee-Soon (College of Pharmacy, Chungbuk National University)
  • 발행 : 2006.04.01

초록

A series of 8-alkyl-and 8-aryl-8,9-dihydro-7H-isoindolo[5,6-g]quinoxaline-7,9-diones were synthesized using sultine chemistry as a key step in good yield. These compounds were evaluated for their in vitro cytotoxicity against six human cancer cell lines (HCT15, SK-OV-3, A549, SNB19, MCF7 and MCF7/ADR).

키워드

참고문헌

  1. Atwell, G. J., Rewcastle, G. W., Baguley, B. C., and Denny, W. A., Potential Antitumor Agents. 50. In vivo solid tumor activity of derivatives of N-[2-(dimethylamino)ethyl]acridine-4-carboxamide. J. Med. Chem., 30, 664-669 (1987) https://doi.org/10.1021/jm00387a014
  2. Baguley, B. C., Zhuang, L., and Marshall, E. M., Experimental solid tumor activity of N-[2-(dimethylamino)ethyl]acridine-4- carboxamide. Cancer Chemother. Pharmacol., 36, 244-248 (1995) https://doi.org/10.1007/BF00685854
  3. Bonner, J. A. and Kozelsky, T. F., The significance of the sequence of administration of topotecan and etoposide. Cancer Chemother. Pharmacol., 39, 109-112 (1996) https://doi.org/10.1007/s002800050545
  4. Brana, M. F. and Ramos, A., Naphthalimides as anti-cancer agents: synthesis and biological activity. Curr. Med. Chem. Anti-Canc. Agents, 3, 237-255 (2001)
  5. Cortes F. and Pinero J., Synergistic effect of inhibitors of topoisomerase I and II on chromosome damage and cell killing in cultured Chinese hamster ovary cells. Cancer Chemother. Pharmacol., 34, 411-5 (1994) https://doi.org/10.1007/BF00685566
  6. Dittrich C., Coudert B., Paz-Ares L., Caponigro F., Salzberg M., Gamucci T., Paoletti X., Hermans C., and Lacombe D., Fumoleau P. and on behalf of the European Organization for Research and Treatment of Cancer-Early Clinical Studies Group/New Drug Development Programme (EORTC-ECSG/ NDDP), Phase II study of XR 5000 (DACA), an inhibitor of topoisomerase I and II, administered as a 120-h infusion in patients with non-small cell lung cancer. European Journal of Cancer, 39, 330-334 (2003) https://doi.org/10.1016/S0959-8049(02)00559-2
  7. Evert, L. D. B., Antonio, E. B., and Emile, E. V., Doxorubicin and mechanical performance of cardiac trabeculae after acute and chronic treatment: a review, Eur. J. Pharmacol., 425, 1- 11 (2001) https://doi.org/10.1016/S0014-2999(01)01143-8
  8. Lee, H., Lee, S. I., Cho, J., Choi, S. U., and Yang, S. I., Synthesis and in vitro evaluation of 1,8-diazaanthraquinon bearing 3-dialkylaminomethyl or 3-(N-alkyl- or N-aryl) carbamoyloxy methyl substituent, Eur. J. Med. Chem., 38, 695-702, (2003) https://doi.org/10.1016/S0223-5234(03)00118-1
  9. Lee, H., Cho, S., Namgoong, K., Jung, J. K., Cho, J., and Yang, S. I., Synthesis and in vitro evaluation of 7-dialkylaminomethylbenzo[ g]quinoxaline-5,10-diones, Bioorg. Med. Chem. Lett., 14, 1235-1237 (2004) https://doi.org/10.1016/j.bmcl.2003.12.046
  10. Lee, H., Cho, S., Choi, B., Namgoong, K., and Jung, J. K., Synthesis of 2,3,8-trisubstituted 7H-Isoindolo[5,6-g]quinoxaline- 5,7,9,11(8H)-tetraones, Heterocycles, 64, 4, 819-826 (2004)
  11. Liu, J. H. and Wu, A. T., The synthesis of pyrazino-containing sultines and their application in Diels-Alder reactions with electron-poor oleffins and [60]fullerene, J. Org. Chem., 65, 3395-3403 (2000) https://doi.org/10.1021/jo9918448
  12. Olson, R. D. and Mushlin, P. S., Doxorubicin cardiotoxicity: analysis of prvailing hypotheses, FASEB J., 4, 3076-3086, (1990) https://doi.org/10.1096/fasebj.4.13.2210154
  13. Priebe, W. Ed. Anthracycline Antibiotics, ACS symposium series 574, Am. Chem. Soc., Washington, DC, 1995
  14. Sivaprakasan, M. and Narshinha, P. A., An efficient synthesis of (${\pm}$)-piliformic acid, J. Chem. Soc. Perkin. Trans., 1, 3290- 3291 (2000)
  15. Skehan, P., Storeng, R., Scudiero, D, Monks, A., McMahon, J., Vistica, D., Warren, J. T., Bokesch, H., Kenny, 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
  16. Stanton, F. R., Thomas, H. J., and Larry, L. M., Electrochemistry and near-infrared spectra of anion radicals containing several imide or quinone groups, J. Org. Chem., 55, 4794-4801 (1990) https://doi.org/10.1021/jo00303a008
  17. Wakelin, L. P. G. and Waring, M. J., DNA Intercalating Agents, In Comprehensive Medicinal Chemistry, Vol 2, 703-724; Hansch, C., Sammes, P. G., Taylor, J. B., Eds.; Pergamon Press: New York, (1990)