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Synthesis and in vitro antitumor activities of xanthone derivatives containing 1,4-disubstituted-1,2,3-triazole moiety

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Abstract

To explore the more active antitumor compounds, two series of new xanthones, containing 1,4-disubstituted-1,2,3-triazole moiety were designed and synthesized. Eaton’s Reagent and “click reaction” were used in the synthesis. Most of the title compounds showed good inhibitory activity against the hepatoma carcinoma cell line (Bel-7402) and human cervical carcinoma cell line (HeLa) in vitro. Compounds 10a, 10e, 10f, 11r and 11t had potent activity with IC50 values, ranging from 2.2 ± 0.17 to 7.1 ± 0.27 ∝M, which was equivalent to Doxorubicin.

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References

  • Abdel-Lateff, A., Klemke, C., Konig, G. M., and Wright, A. D., Two new xanthone derivatives from the algicolous marine fungus Wardomyces anomalus. J. Nat. Prod., 66, 706–708 (2003).

    Article  PubMed  CAS  Google Scholar 

  • Chung, M. I., Weng, J. R., Wang, J. P., Teng, C. M., and Lin, C. N., Antiplatelet and anti-inflammatory constituents and new oxygenated xanthones from Hypericum geminiflorum. Planta Med., 68, 25–29 (2002).

    Article  PubMed  CAS  Google Scholar 

  • Eaton, P. E., Carlson, G. R., and Lee, J. T., Phosphorus pentoxide-methanesulfonic acid. Convenient alternative to polyphosphoric acid. J. Org. Chem., 38, 4071–4073 (1973).

    Article  CAS  Google Scholar 

  • El Akri, K., Bougrin, K., Balzarini, J., Faraj, A., and Benhida, R., Efficient synthesis and in vitro cytostatic activity of 4-substituted triazolyl-nucleosides. Bioorg. Med. Chem. Lett., 17, 6656–6659 (2007).

    Article  PubMed  Google Scholar 

  • Fernandes, E. R., Carvalho, F. D., Remiao, F. G., Bastos, M. L., Pinto, M. M., and Gottlieb, O. R., Hepatoprotective activity of xanthones and xanthonolignoids against tert-butylhydroperoxide-induced toxicity in isolated rat hepatocytes-comparison with silybin. Pharm. Res., 12, 1756–1760 (1995).

    Article  PubMed  CAS  Google Scholar 

  • Hu, H., Liao, H., Zhang, J., Wu, W., Yan, J., Yan, Y., Zhao, Q., Zou, Y., Chai, X., Yu, S., and Wu, Q., First identification of xanthone sulfonamides as potent acyl-CoA:cholesterol acyltransferase (ACAT) inhibitors. Bioorg. Med. Chem. Lett., 20, 3094–3097 (2010).

    Article  PubMed  CAS  Google Scholar 

  • Kamal, A., Shankaraiah, N., Devaiah, V., Laxma Reddy, K., Juvekar, A., Sen, S., Kurian, N., and Zingde, S., Synthesis of 1,2,3-triazole-linked pyrrolobenzodiazepine conjugates employing ‘click’ chemistry: DNA-binding affinity and anticancer activity. Bioorg. Med. Chem. Lett., 18, 1468–1473 (2008).

    Article  PubMed  CAS  Google Scholar 

  • Kostakis, I. K., Pouli, N., Marakos, P., Kousidou, O., Roussidis, A., Tzanakakis, G. N., and Karamanos, N. K., Design, synthesis and cell growth inhibitory activity of a series of novel aminosubstituted xantheno[1,2-d]imidazoles in breast cancer cells. Bioorg. Med. Chem., 16, 3445–3455 (2008).

    Article  PubMed  CAS  Google Scholar 

  • Mahabusarakam, W., Proudfoot, J., Taylor, W., and Croft, K., Inhibition of lipoprotein oxidation by prenylated xanthones derived from mangostin. Free Radic. Res., 33, 643–659 (2000).

    Article  PubMed  CAS  Google Scholar 

  • Malnuit, V., Duca, M., Manout, A., Bougrin, K., and Benhida, R., Tandem azide-alkyne 1,3-dipolar cycloaddition/electrophilic addition: a concise three-component route to 4,5-disubstituted triazolyl-nucleosides. Synlett, 2009, 2123–2126 (2009).

    Article  Google Scholar 

  • Moody, T. W., Chiles, J., Moody, E., Sieczkiewicz, G. J., and Kohn, E. C., CAI inhibits the growth of small cell lung cancer cells. Lung Cancer, 39, 279–288 (2003).

    Article  PubMed  Google Scholar 

  • Park, K. H., Park, Y. D., Han, J. M., Im, K. R., Lee, B. W., Jeong, I. Y., Jeong, T. S., and Lee, W. S., Anti-atherosclerotic and anti-inflammatory activities of catecholic xanthones and flavonoids isolated from Cudrania tricuspidata. Bioorg. Med. Chem. Lett., 16, 5580–5583 (2006).

    Article  PubMed  CAS  Google Scholar 

  • Pautus, S., Yee, S. W., Jayne, M., Coogan, M. P., and Simons, C., Synthesis and CYP26A1 inhibitory activity of 1-[benzofuran-2-yl-(4-alkyl/aryl-phenyl)-methyl]-1H-triazoles. Bioorg. Med. Chem., 14, 3643–3653 (2006).

    Article  PubMed  CAS  Google Scholar 

  • Peres, V., Nagem, T. J., and De Oliveira, F. F., Tetraoxygenated naturally occurring xanthones. Phytochemistry, 55, 683–710 (2000).

    Article  PubMed  CAS  Google Scholar 

  • Pinto, M. M., Sousa, M. E., and Nascimento, M. S., Xanthone derivatives: new insights in biological activities. Curr. Med. Chem., 12, 2517–2538 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Rivera, D. G., Balmaseda, I. H., Leon, A. A., Hernandez, B. C., Montiel, L. M., Garrido, G. G., Cuzzocrea, S., and Hernandez, R. D., Anti-allergic properties of Mangifera indica L. extract (Vimang) and contribution of its glucosylxanthone mangiferin. J. Pharm. Pharmacol., 58, 385–392 (2006).

    Article  PubMed  Google Scholar 

  • Tanaka, N., Kashiwada, Y., Kim, S.-Y., Sekiya, M., Ikeshiro, Y., and Takaishi, Y., Xanthones from Hypericum chinense and their cytotoxicity evaluation. Phytochemistry, 70, 1456–1461 (2009).

    Article  PubMed  CAS  Google Scholar 

  • Vieira, L. M. and Kijjoa, A., Naturally-occurring xanthones: recent developments. Curr. Med. Chem., 12, 2413–2446 (2005).

    Article  PubMed  CAS  Google Scholar 

  • Woo, S., Jung, J., Lee, C., Kwon, Y., and Na, Y., Synthesis of new xanthone analogues and their biological activity test—Cytotoxicity, topoisomerase II inhibition, and DNA crosslinking study. Bioorg. Med. Chem. Lett., 17, 1163–1166 (2007).

    Article  PubMed  CAS  Google Scholar 

  • Zeytinoglu, H., Incesu, Z., and Baser, K. H., Inhibition of DNA synthesis by carvacrol in mouse myoblast cells bearing a human N-RAS oncogene. Phytomedicine, 10, 292–299 (2003).

    Article  PubMed  CAS  Google Scholar 

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Correspondence to Mingjuan Xu or Qiuye Wu.

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These authors contributed equally to this work.

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Zou, Y., Zhao, Q., Hu, H. et al. Synthesis and in vitro antitumor activities of xanthone derivatives containing 1,4-disubstituted-1,2,3-triazole moiety. Arch. Pharm. Res. 35, 2093–2104 (2012). https://doi.org/10.1007/s12272-012-1206-4

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  • DOI: https://doi.org/10.1007/s12272-012-1206-4

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