Synthesis and antimicrobial and antifungal activities of cyclopentene β, β'-triketones and their methyl enol ethers

The natural cyclopentene β, β'-triketone coruscanone B and its methyl enol ether coruscanone A, metabolites of the higher plant Piper coruscans, in addition to 19 of their simple analogs have been synthesized. The antimicrobial activity of the synthesized compounds against Gram-positive (Staphylococcus aureus ATCC 21027) and Gram-negative (Escherichia coli ATCC 15034) bacteria, yeast (Sofale S-04 and Candida albicans KMM455), and fungi (Aspergillus niger KMM4634 and Fusarium oxysporum KMM4639) was studied. The nature and number of substituents at the 4- and 5-positions of the five-membered ring and also the nature of the substituent in the 2-position were found to have a profound effect on the level of activity and the spectrum of antimicrobial action of the tested compounds. Free β, β'ect. It is established that the level of activity and the spectrum of the antimicrobial action of coruscanone A and 2-(1-methoxyethylidene)-4,5-dichlorocyclopent-4-ene-1,3-dione are almost identical to those of the reference drug nitrofungin.

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

References

  1. 1.

    X.-C. Li, D. Ferreira, M. R. Jacob, et al., J. Am. Chem. Soc., 126, 6872 – 6873 (2004).

    Article  CAS  PubMed  Google Scholar 

  2. 2.

    E. I. Hwang, Y. M. Lee, S. M. Lee, et al., Planta Med., 73, 679 – 682 (2007).

    Article  CAS  PubMed  Google Scholar 

  3. 3.

    S.-Y. Wang, X.-Y. Lan, J.-H. Xiao, et al., Phytother. Res., 22, 213 – 216 (2008).

    Article  CAS  PubMed  Google Scholar 

  4. 4.

    G. Gilardoni, M. Clericuzio, S. Tosi, et al., J. Nat. Prod., 70, 137 – 139 (2007).

    Article  CAS  PubMed  Google Scholar 

  5. 5.

    K. S. Babu, X.-C. Li, M. R. Jacob, et al., J. Med. Chem., 49, 7877 – 7886 (2006).

    Article  CAS  PubMed  Google Scholar 

  6. 6.

    Y. Aoyama, T. Konoike, A. Kanda, et al., Bioorg. Med. Chem. Lett., 11, 1695 – 1697 (2001).

    Article  CAS  PubMed  Google Scholar 

  7. 7.

    H. M. Oh, S. K. Choi, J. M. Lee, et al., Bioorg. Med. Chem., 13, 6182 – 6187 (2005).

    Article  CAS  PubMed  Google Scholar 

  8. 8.

    B. S. Min, K. H. Bae, Y. H. Kim, et al., Nat. Prod. Sci., 4, 241 – 244 (1998).

    CAS  Google Scholar 

  9. 9.

    O. P. Shestak, V. L. Novikov, and S. I. Stekhova, Khim.-farm. Zh., 33(1), 18 – 21 (1999).

    CAS  Google Scholar 

  10. 10.

    S. Forsen, F. Merenyi, and M. Nilsson, Acta Chem. Scand., 18, 1208 – 1221 (1964).

    Article  CAS  Google Scholar 

  11. 11.

    D. V. Berdyshev, V. P. Glazunov, and V. L. Novikov, in: Abstracts of Papers of the VIth All-Russian Scientific Seminar “Chemistry and Medicine” [in Russian], Ufa (2007), pp. 133 – 135.

  12. 12.

    D. V. Berdyshev, Yu. G. Izrailskii, V. L. Novikov, et al., in: Proceedings of the 1st Far-Eastern Intern. Symp. on Life Sciences [in Russian], Vladivostok (2008), pp. 13 – 14.

  13. 13.

    V. L. Novikov, O. P. Shestak, N. N. Balaneva, et al., Izv. Akad. Nauk Latv. SSR, Ser. Khim., No. 6, 718 – 724 (1985).

  14. 14.

    V. L. Novikov, O. P. Shestak, A. V. Kamernitskii, et al., Izv. Akad. Nauk SSSR, Ser. Khim., No. 6, 1390 – 1393 (1980).

    Google Scholar 

  15. 15.

    A. A. Akhrem, F. A. Lakhvich, and N. A. Fil'chenkov, Zh. Org. Khim., No. 15, 2333 – 2337 (1979).

  16. 16.

    E. P. Ivanova, D. V. Nicolau, N. Yumoto, et al., Mar. Biol., 130, 545 – 551 (1998).

    Article  Google Scholar 

Download references

Author information

Affiliations

Authors

Corresponding author

Correspondence to O. P. Shestak.

Additional information

Translated from Khimiko-Farmatsevticheskii Zhurnal, Vol. 43, No. 9, pp. 16 – 19, September, 2009.

Rights and permissions

Reprints and Permissions

About this article

Cite this article

Shestak, O.P., Novikov, V.L., Martyyas, E.A. et al. Synthesis and antimicrobial and antifungal activities of cyclopentene β, β'-triketones and their methyl enol ethers. Pharm Chem J 43, 498 (2009). https://doi.org/10.1007/s11094-009-0338-4

Download citation

Key words

  • cyclopentene β, β'-triketones
  • 2-acylcyclopent-4-ene-1,3-diones
  • methyl enol ethers of cyclopentene β, β'-triketones
  • 2-(1'-methoxyethylidene)cyclopent-4-ene-1,3-diones
  • coruscanones A and B
  • Gram-positive and Gram-negative bacteria
  • yeasts
  • fungi
  • antibacterial and antifungal activities.