Skip to main content
Log in

α-Amino acid-derived 2-phenylimidazoles with potential antimycobacterial activity

  • Research Article
  • Published:
Central European Journal of Chemistry

Abstract

α-Amino acid-derived 2-phenylimidazole derivatives were designed, synthesized, and further investigated as potential antimycobacterial agents. The synthesis of target imidazole derivatives involved the transformation of Cbz-protected α-amino acids (Ala, Val, Phe, Leu, iLe, and Pro) into α-diazoketones and α-bromoketones, respectively. Subsequent treatment of α-bromoketones with (4-nitro)benzamidine afforded imidazole derivatives bearing α-amino acid residue appended to the imidazole C4 and (4-nitro)phenyl ring in the position C2. Antimycobacterial activities of both series of compounds against M. tuberculosis, M. avium, and M. kansasii were screened and basic structure-activity relationships were further evaluated.

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

Access this article

Subscribe and save

Springer+ Basic
EUR 32.99 /Month
  • Get 10 units per month
  • Download Article/Chapter or Ebook
  • 1 Unit = 1 Article or 1 Chapter
  • Cancel anytime
Subscribe now

Buy Now

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

Instant access to the full article PDF.

Similar content being viewed by others

References

  1. S. T. Cole, G. Riccardi, Curr. Opin. Microbiol. 14, 570 (2011)

    Article  CAS  Google Scholar 

  2. D.E. Griffith, T. Aksamit, B.A. Brown-Elliott, A. Catanzaro, C. Daley, F. Gordin, S.M. Holland, R. Horsburgh, G. Huitt, M.F. Iademarco, M. Iseman, K. Olivier, S. Ruoss, C.F. von Reyn, R.J. Wallace Jr., K. Winthrop, Am. J. Resp. Crit. Care, 175, 367 (2007)

    Article  CAS  Google Scholar 

  3. L. Ballel, R.A. Field, K. Duncan, R.J. Young, Antimicrob. Agents Chemother. 49, 2153 (2005)

    Article  Google Scholar 

  4. R.J. O’Brien, M. Spigelman, Clin. Chest. Med. 26, 327 (2005)

    Article  Google Scholar 

  5. M. Krátký, J. Vinšová, Chem. Listy 104, 998 (2010)

    Google Scholar 

  6. M. Biava, G.C. Porretta, G. Poce, A. De Logu, R. Meleddu, E. De Rossi, F. Manetti, M. Botta, Eur. J. Med. Chem. 44, 4734 (2009)

    Article  CAS  Google Scholar 

  7. D. Deidda, G. Lampis, R. Fioravanti, M. Biava, G.C. Porretta, S. Zanetti, R. Pompei, Antimicrob. Agents Chemother. 42, 3035 (1998)

    CAS  Google Scholar 

  8. A. Lilienkampf, M. Pieroni, B. Wan, Y. Wang, S.G. Franzblau, A.P. Kozikowski, J. Med. Chem. 53, 678 (2010)

    Article  CAS  Google Scholar 

  9. G. Navarrete-Vázquez, G.M. Molina-Salinas, Z.V. Duarte-Fajardo, J. Vargas-Villarreal, S. Estrada-Soto, F. Gonzáles-Salazar, E. Hernández-Núñez, S. Said-Fernández, Bioorg. Med. Chem. 15, 5502 (2007)

    Article  Google Scholar 

  10. M. Boiani, M. González, Mini-Rev. Med. Chem. 5, 409 (2005)

    Article  CAS  Google Scholar 

  11. L. De Luca, Curr. Med. Chem. 13, 1 (2006)

    Article  Google Scholar 

  12. F. Bellina, S. Cauteruccio, R. Rossi, Tetrahedron 63, 4571 (2007)

    Article  CAS  Google Scholar 

  13. B. Dolensky, G. Nam, W.-P. Deng, J. Narayanan, J. Fan, K. L. Kirk, J. Fluorine Chem. 125, 501 (2004)

    Article  CAS  Google Scholar 

  14. C.K. Stover, P. Warrener, D.R. VanDevanter, D.R. Sherman, T.R. Arain, M.H. Langhorne, S.W. Anderson, J.A. Towell, Y. Yuan, D.N. McMurray, B.N. Kreiswirth, C.E. Barry, W.R. Baker, Nature 405, 962 (2000)

    Article  CAS  Google Scholar 

  15. M. Matsumoto, H. Hashizume, T. Tomishige, M. Kawasaki, H. Tsubouchi, H. Sasaki, Y. Shimokawa, M. Komatsu, PLoS Med. 3, 2131 (2006)

    Article  CAS  Google Scholar 

  16. P. Pařík, J. Jansa, S. Holešová, A. Marek, V. Klimešová, J. Heterocyclic Chem., accepted (2012)

  17. O. Pytela, V. Klimešová, Chem. Pharm. Bull. 59, 179 (2011)

    Article  CAS  Google Scholar 

  18. W.O. Foye, T.L. Lemke, D.A. Williams, Foye’s principles of medicinal chemistry, 6th edition (Lippincott Williamsїlkins, a Wolters Kluwer, Baltimore, 2008)

    Google Scholar 

  19. F. Bureš, J. Kulhánek, Tetrahedron:Asymmetry 16, 1347 (2005)

    Article  Google Scholar 

  20. F. Bureš, T. Szotkowski, J. Kulhánek, O. Pytela, M. Ludwig, M. Holčapek, Tetrahedron: Asymmetry 17, 900 (2006)

    Article  Google Scholar 

  21. A. Marek, J. Kulhánek, M. Ludwig, F. Bureš, Molecules 12, 1183 (2007)

    Article  CAS  Google Scholar 

  22. A. Marek, J. Kulhánek, F. Bureš, Synthesis 325 (2009)

  23. A. Marek, J. Kulhánek, W. B. Schweizer, F. Bureš, Synthesis 3188 (2010).

  24. F. Bureš, PhD thesis (University of Pardubice, Pardubice, Czech Republic, 2005)

  25. F.C. Schaefer, G.A. Peters, J. Org. Chem. 26, 412 (1961)

    Article  CAS  Google Scholar 

  26. A.R. Katritzky, A.F. Pozharskii, Handbook of heterocyclic chemistry, 2nd edition (Elsevier Science Ltd, Oxford, 2000)

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to Filip Bureš.

About this article

Cite this article

Cvejn, D., Klimešová, V. & Bureš, F. α-Amino acid-derived 2-phenylimidazoles with potential antimycobacterial activity. cent.eur.j.chem. 10, 1681–1687 (2012). https://doi.org/10.2478/s11532-012-0087-1

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.2478/s11532-012-0087-1

Keywords

Navigation