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4β-Isocyanopodophyllotoxins: valuable precursors for the synthesis of new podophyllotoxin analogues

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Abstract

A new and efficient method for the synthesis of novel 4β-isocyanopodophyllotoxins as a valuable building block for the synthesis of versatile bioactive podophyllotoxin analogues under both classical and ultrasonic conditions was developed. In general, significant improvements in rates of reaction and yields of sonochemical reactions relative to the classical ones were observed.

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References

  • Bohlin, L., & Rosen, B. (1996). Podophyllotoxin derivatives: drug discovery and development. Drug Discovery Today, 1, 343–351. DOI: 10.1016/1359-6446(96)10028-3.

    Article  CAS  Google Scholar 

  • Bon, R. S., van Vliet, B., Sprenkels, N. E., Schmitz, R. F., de Kanter, F. J. J., Stevens, C. V., Swart, M., Bickelhaupt, F. M., Groen, M. B., & Orru, R. V. (2005). Multicomponent synthesis of 2-imidazolines. The Journal of Organic Chemistry, 70, 3542–3553. DOI: 10.1021/jo050132g.

    Article  CAS  Google Scholar 

  • Bremner, W. S., & Organ, M. G. (2007). Multicomponent reactions to form heterocycles by microwave-assisted continuous flow organic synthesis. Journal of Combinatorial Chemistry, 9, 14–16. DOI: 10.1021/cc060130p.

    Article  CAS  Google Scholar 

  • Dömling, A. (2006). Recent developments in isocyanide based multicomponent reactions in applied chemistry. Chemical Reviews, 106, 17–89. DOI: 10.1021/cr0505728.

    Article  Google Scholar 

  • Dömling, A., & Ugi, I. (2000). Multicomponent reactions with isocyanides. Angewandte Chemie International Edition, 39, 3168–3210. DOI: 10.1002/1521-3773(20000915)39:18<3168::AID-ANIE3168>3.0.CO;2-U.

    Google Scholar 

  • Dolle, R. E., Le Bourdonnec, B., Goodman, A. J., Morales, G. A., Thomas, C. J., & Zhang, W. (2009). Comprehensive survey of chemical libraries for drug discovery and chemical biology: 2008. Journal of Combinatorial Chemistry, 11, 739–790. DOI: 10.1021/cc9000828.

    Article  CAS  Google Scholar 

  • El Kaim, L., Gizzi, M., Ĝrimaud, L. (2008). New MCR-Heckisomerization cascade toward indoles. Organic Letters, 10, 3417–3419. DOI: 10.1021/ol801217a.

    Article  Google Scholar 

  • Gordaliza, M., García, P. A., Miguel del Corral, J. M., Castro, M. A., & Gómez-Zurita, M. A. (2004). Podophyllotoxin: distribution, sources, applications and new cytotoxic derivatives. Toxicon, 44, 441–459. DOI: 10.1016/j.toxicon.2004.05.008.

    Article  CAS  Google Scholar 

  • Katritzky, A. R., Xie, L., & Fan, W.-Q. (1993). Synthesis of α-amino isocyanides and α-alkylthio isocyanides. Synthesis, 1993, 45–47. DOI: 10.1055/s-1993-25788.

    Article  Google Scholar 

  • Liu, Y.-Q., Li, L.-H., Yang, L., & Li, H.-Y. (2010). A novel, stereoselective and practical protocol for the synthesis of 4β-aminopodophyllotoxins. Chemical Papers, 64, 533–536. DOI: 10.2478/s11696-010-0020-z.

    Article  CAS  Google Scholar 

  • Liu, Y.-Q., Liu, Y., Xiao, H., Gao, R., & Tian, X. (2008). Synthesis and insecticidal activities of novel derivatives of podophyllotoxin: Part XII. Pesticide Biochemistry and Physiology, 91, 116–121. DOI: 10.1016/j.pestbp.2008.03.002.

    Article  CAS  Google Scholar 

  • Liu, Q. Y., Liu, Y., & Xuan, T. (2007). Podophyllotoxin: Current perspectives. Current Bioactive Compounds, 3, 37–66. DOI: 10.2174/157340707780126499.

    Article  CAS  Google Scholar 

  • Nair, V., Vinod, A. U., & Rajesh, C. (2001). A novel synthesis of 2-aminopyrroles using a three-component reaction. The Journal of Organic Chemistry, 66, 4427–4429. DOI: 10.1021/jo001714v.

    Article  CAS  Google Scholar 

  • Roulland, E., Magiatis, P., Arimondo, P., Bertounesque, E., & Monneret, C. (2002). Hemi-synthesis and biological activity of new analogues of podophyllotoxin. Bioorganic & Medicinal Chemistry, 10, 3463–3471. DOI: 10.1016/S0968-0896(02)00255-9.

    Article  CAS  Google Scholar 

  • Shaabani, A., Maleki, A., Mofakham, H., & Khavasi, H. R. (2008). Novel isocyanide-based three-component onepot synthesis of cyanophenylamino-acetamide derivatives. Journal of Combinatorial Chemistry, 10, 883–885. DOI: 10.1021/cc800099r.

    Article  CAS  Google Scholar 

  • Touré, B. B., & Hall, D. G. (2009). Natural product synthesis using multicomponent reaction strategies. Chemical Reviews, 109, 4439–4486. DOI: 10.1021/cr800296p.

    Article  Google Scholar 

  • Wang, Z. Q., Kuo, Y. H., Schnur, D., Bowen, J. P., Liu, S. Y., Han, F. S., Chang, J. Y., Cheng, Y. C., & Lee, K. H. (1990). Antitumor agents. 113. New 4β-arylamino derivatives of 4′-O-demethylepipodophyllotoxin and related compounds as potent inhibitors of human DNA topoisomerase II. Journal of Medicinal Chemistry, 33, 2660–2666. DOI: 10.1021/jm00171a050.

    Article  CAS  Google Scholar 

  • Xu, H., Wang, J., Sun, H., Lv, M., Tian, X., Yao, X., & Zhang, X. (2009). Semisynthesis and quantitative structure-activity relationship (QSAR) study of novel aromatic esters of 4′-demethyl-4-deoxypodophyllotoxin as insecticidal agents. Journal of Agricultural and Food Chemistry, 57, 7919–7923. DOI: 10.1021/jf9020812.

    Article  CAS  Google Scholar 

  • Yu, Y.-P., Chen, S.-Y., Wang, Y.-G., & Chen, Y.-Z. (1999). A facile and efficient synthesis of 4β-aminopodophyllotoxins. Tetrahedron Letters, 40, 1967–1970. DOI: 10.1016/S0040-4039(99)00125-2.

    Article  CAS  Google Scholar 

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Correspondence to Ying-Qian Liu.

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Liu, YQ., Li, LH., Li, WQ. et al. 4β-Isocyanopodophyllotoxins: valuable precursors for the synthesis of new podophyllotoxin analogues. Chem. Pap. 65, 739–742 (2011). https://doi.org/10.2478/s11696-011-0062-x

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