Skip to main content
SpringerLink
Log in

Synthesis and Bioactivity of N-(4-(N′-Substituted Sulfamoyl)Phenyl)Myrtenamides Containing a Heterocycle

  • Published:
Chemistry of Natural Compounds Aims and scope

A series of N-(4-(N′-substituted sulfamoyl)phenyl)myrtenamides containing a heterocycle were designed and synthesized by a multiple-step procedure using α-pinene as starting material. All the synthesized compounds were characterized and analyzed by GC, HPLC, UV-vis, FTIR, NMR, GC-MS, and ESI-MS. The preliminary bioassay showed that, at 50 μg/mL, the target compounds exhibited a certain antifungal activity against the five tested fungi, in which compound 5f exhibited antifungal activity of 83.2% and 70.0% against Physalospora piricola and Alternaria solani, respectively. Moreover, compound 5d displayed herbicidal activity of 86.0% against the root of rape (Brassica campestris) at 100 μg/mL.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Similar content being viewed by others

References

  1. A. C. R. Silva, P. M. Lpoes, M. M. B. Azevedo, D. C. M. Costa, C. S. Alviano, and D. S. Alviano, Molecules, 17, 6305 (2012).

    Article  PubMed  Google Scholar 

  2. E. Aydin, H. Turkez, and F. Geyikoglu, Biologia, 68, 1004 (2013).

    Article  CAS  Google Scholar 

  3. D. R. Miller and R. J. Rabaglia, J. Chem. Ecol., 35, 435 (2009).

    Article  CAS  PubMed  Google Scholar 

  4. J. H. Lu, M. G. Lin, and Y. W. Tu, J. Chin. Cereals Oils Assoc., 25, 88 (2010).

    CAS  Google Scholar 

  5. G. S. Lin, C. H. Ma, W. G. Duan, B. Cen, F. H. Lei, and Z. Q. Yang, Holzforschung, 68, 75 (2014).

    CAS  Google Scholar 

  6. B. S. Wei, W. Gu, X. Xu, Y. Q. Yang, and S. F. Wang, Chin. J. Org. Chem., 33, 2196 (2013).

    Article  CAS  Google Scholar 

  7. H. Kameoka and K. Nakai, Nippon Nogei Kagaku Kaishi, 61, 1119 (1987).

    Article  CAS  Google Scholar 

  8. A. Ateeque and L. N. Misra, Phytochemistry, 37, 183 (1994).

    Article  Google Scholar 

  9. D. Vegezzi, U. S. Pat. 4 190 675 (1980).

  10. S. Kamchonwongpaisan, C. Nilanonta, B. Tamchompoo, C. Thebtaranonth, Y. Thebtaranonth, Y. Yuthavong, P. Kongsaeree, and J. Clardy, Tetrahedron Lett., 36, 1821 (1995).

    Article  CAS  Google Scholar 

  11. H. B. Lingaiah, N. Natarajan, R. Thamaraiselvan, P. Srinivasan, and B. M. Periyasamy, Fundam. Clin. Pharmacol., 27, 443 (2013).

    Article  CAS  PubMed  Google Scholar 

  12. W. N. Setzer, B. Vogler, J. M. Schmidt, J. G. Leahy, and R. Rives, Fitoterapia, 75, 192 (2004).

    Article  CAS  PubMed  Google Scholar 

  13. J. Hardie, R. Isaacs, J. A. Pickett, L. J. Wadhams, and C. M. Woodcock, J. Chem. Ecol., 20, 2847 (1994).

    Article  CAS  PubMed  Google Scholar 

  14. L. Peng, C. X. Yin, F. M. Zhang, Y. H. Liu, and N. Zhou, Chem. Bioeng., 30, 50 (2013).

    CAS  Google Scholar 

  15. S. Tachibana, Y. Ohno, Y. Fujihara, Y. Okada, M. Sugiura, S. Takagi, and M. Nomura, J. Oleo Sci., 55, 181 (2006).

    Article  CAS  Google Scholar 

  16. J. L. Castro, R. Baker, A. R. Guiblin, S. C. Hobbs, M. R. Jenkins, M. G. N. Russell, M. S. Beer, J. A. Stanton, and K. Scholey, J. Med. Chem., 37, 3023 (1994).

    Article  CAS  PubMed  Google Scholar 

  17. J. L. Archibald, D. R. Beardsley, T. J. Ward, J. F. Waterfall, and J. F. White, J. Med. Chem., 26, 416 (1983).

    Article  CAS  PubMed  Google Scholar 

  18. S. Beaudoin, K. E. Kinsey, and J. F. Burns, J. Org. Chem., 68, 115 (2002).

    Article  Google Scholar 

  19. M. E. Arranz, J. A. Diaz, S. T. Ingate, M. Witvrouw, C. Pannecouque, J. Balzarini, E. D. Clercq, and S. Vega, Bioorg. Med. Chem., 7, 2811 (1999).

    Article  CAS  PubMed  Google Scholar 

  20. R. Kuang, J. B. Epp, S. Ruan, H. Yu, P. Huang, S. He, J. Tu, N. M. Schechter, J. Turbov, G. J. Froelich, and W. C. Groutas, J. Am. Chem. Soc., 121, 8128 (1999).

    Article  CAS  Google Scholar 

  21. E. Mishani, G. Abourbeh, Y. Rozen, O. Jacobson, D. Laky, I. B. Davida, A. Levitzki, and M. Shaul, Nucl. Med. Biol., 31, 469 (2004).

    Article  CAS  PubMed  Google Scholar 

  22. G. P. Lahm, D. Cordova, and J. D. Barry, Bioorg. Med. Chem., 17, 4127 (2009).

    Article  CAS  PubMed  Google Scholar 

  23. G. S. Wu, W. G. Duan, G. S. Lin, B. Cen, L. Zhao, and F. H. Lei, Chin. J. Pestic. Sci., 16, 8 (2014).

    CAS  Google Scholar 

  24. M. Z. Huang, X. Y. Luo, Y. G. Ren, C. L. Zhang, L. Zhang, and M. C. Xu, Chin. J. Pestic. Sci., 9, 76 (2007).

    Google Scholar 

  25. Y. Xu, S. J. Xue, J. F. Sun, Z. K. Fang, A. Q. Yin, and L. Chen, Chin. J. Org. Chem., 28, 1997 (2008).

    CAS  Google Scholar 

  26. Q. J. Mo, W. G. Duan, X. L. Ma, G. S. Lin, X. T. Xu, and B. Cen, Huaxue Tongbao, 75, 160 (2012).

    CAS  Google Scholar 

  27. H. E. Eschinazi and H. Pines, J. Org. Chem., 24, 1369 (1959).

    Article  CAS  Google Scholar 

  28. J. M. Coxon, G. J. Hydes, and P. J. Steel, J. Chem. Soc. Perkin Trans., 2, 1351 (1984).

    Article  Google Scholar 

  29. M. Nomura, Y. Fujihara, T. Hamada, T. Hirokawa, and K. Tsuzuki, Nippon Nogei Kagaku Kaishi, 66, 1771 (1992).

    Article  CAS  Google Scholar 

  30. B. Wiese, G. Knuhl, D. Flubacher, J. W. Prieβ, K. Brodner, and G. Helmchen, Eur. J. Org. Chem., 2005, 3246 (2005).

    Article  Google Scholar 

Download references

Acknowledgment

This work was supported by the National Natural Science Foundation of China (No. 31460173) and the open fund of Guangxi Key Laboratory of Chemistry and Engineering of Forest Products (No. GXFC13-02). The authors are grateful to the Research Institute of Element-Organic Chemistry, Nankai University, P. R. China, for the bioassay test.

Author information

Authors and Affiliations

  1. School of Chemistry and Chemical Engineering, Guangxi University, Nanning, 530004, Guangxi, P. R. China

    Guishan Lin, Wengui Duan, Hongqiang Liu & Yuan Ma

  2. Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning, 530008, Guangxi, P. R. China

    Fuhou Lei

Authors
  1. Guishan Lin
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Wengui Duan
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Hongqiang Liu
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Yuan Ma
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Fuhou Lei
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Wengui Duan.

Additional information

Published in Khimiya Prirodnykh Soedinenii, No. 1, January–February, 2018, pp. 52–57.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Lin, G., Duan, W., Liu, H. et al. Synthesis and Bioactivity of N-(4-(N′-Substituted Sulfamoyl)Phenyl)Myrtenamides Containing a Heterocycle. Chem Nat Compd 54, 56–62 (2018). https://doi.org/10.1007/s10600-018-2258-6

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10600-018-2258-6

Keywords

Search

Navigation