Skip to main content
SpringerLink
Log in

Microwave-assisted synthesis and antibacterial activity of some pyrazol-1-ylquinoxalin- 2(1H)-one derivatives

  • Published:
Chemistry of Heterocyclic Compounds Aims and scope

3-Hydrazinoquinoxalin-2(1H)-one was prepared from quinoxaline-2,3-dione and subsequently used for the synthesis of some potentially biologically active 3-(pyrazol-1-yl)quinoxalin-2(1H)-one derivatives. While 3-(3,5-dimethylpyrazol-1-yl)quinoxalin-2(1H)-one showed a comparative effect with streptomycin, 3-(5-oxo-3-phenyl-4,5-di- hydropyrazol-1-yl)quinoxalin-2(1H)-one was found to be the most active with an MIC value of 7.8 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. L. Zhenjiang, L. Weisi, S. Yingjie, and H. He, O. Pingkai, J. Heterocycl. Chem., 45, 285 (2008).

    Article  Google Scholar 

  2. C. A. Obafemi, G. Olayiwola, and F. O. Taiwo, African J. Biotech., 6, 777 (2007).

    Google Scholar 

  3. G. S. Welmaker, J. A. Nelson, J. E. Sabalski, A. L. Sabb, J. R. Potoski, D. Graziano, M. Kagan, J. Coupet, J. Dunlop, H. Mazandarani, S. Rosenzweig-Lipson, S. Sukoff, and Y. Zhang, Bioorg. Med. Chem. Lett., 10, 1991 (2000).

    Article  CAS  Google Scholar 

  4. M. A. J. Al-Mossawi, A. A. Salem, M. Salam, and A. Arani, Environ. Int., 5, 141 (1981).

    Article  CAS  Google Scholar 

  5. H. M. Refaat, A. A. Moneer, and O. M. Khalil, Arch. Pharm. Res., 27, 1093 (2004).

    Article  CAS  Google Scholar 

  6. M. M. Ali, M. M. F. Ismail, M. S. A. El-Gaby, M. A. Zahran, and Y. A. Ammar, Molecules, 5, 864 (2000).

    Article  CAS  Google Scholar 

  7. C. A. Obafemi and D. A. Akinpelu, Phosphorus, Sulfur, Silicon, Relat. Elem., 180, 1795 (2005).

    Article  CAS  Google Scholar 

  8. Ch. Sridevi, K. Balaji, A. Naidu, S. Kavimani, D. Vankappayya, R. Suthakaran, and S. Parimala, Int. J. Pharmatech. Res., 1, 816 (2009).

    CAS  Google Scholar 

  9. A. Carta, P. Sanna, U. D. Gherardini, and S. Zanetti, Farmaco, 56, 933 (2001).

    Article  CAS  Google Scholar 

  10. P. Sanna, A. Carta, M. Loriga, S. Zanetti, and L. Sechi, Farmaco, 54, 161 (1999).

    Article  CAS  Google Scholar 

  11. M. A. H. Hamida, Carbohydr. Res., 338, 2301 (2003).

    Article  Google Scholar 

  12. J. B. Rangisetty, C. N. V. H. B. Gupta, A. L. Prasad, P. Srinivas, N. Sridhar, P. Parimoo, and A. Veeranjaneyulu, J. Pharm. Pharmacol., 53, 1409 (2001).

    Article  CAS  Google Scholar 

  13. M. Kodama, N. Yamada, K. Sato, Y. Kitamura, F. Koyama, T. Sato, K. Morimoto, and S. Kuroda, Eur. J. Pharmacol., 374, 11 (1999).

    Article  CAS  Google Scholar 

  14. R. Sarge, H. R. Howard, R. G. Browne, L. A. Lebel, P. A. Seymour, and B. K. Kve, J. Med. Chem., 33, 2240 (1990).

    Article  Google Scholar 

  15. A. Jaso, B. Zarranz, I. Aldana, and A. Mongye, Eur. J. Med. Chem., 38, 791 (2003).

    Article  CAS  Google Scholar 

  16. M. M. Badran, K. A. M. Abouzid, and M. H. M. Hussein, Arch. Pharm. Res., 26, 107 (2003).

    Article  CAS  Google Scholar 

  17. U. J. Ries, H. W. Priekpe, N. H. Havel, S. Haandschuh, G. Mihm, J. M. Stassen, W. Wienen, and H. Nar, Bioorg. Med. Chem. Lett., 13, 2297 (2003).

    Article  CAS  Google Scholar 

  18. L. Fengcai, W. Baigeng, and C. Jinbao, Polym. Sci. Tech., 26, 261 (1984).

    Google Scholar 

  19. J. P. Critchley, (editor), Polymers: thermally stable quinoxaline polymers, in: Encycopedia of Physical Science and Technology, 3rd ed., Acad. Press, 2002, p. 775.

  20. A. F. R. Sherif, A. S. Manal, and A. E.-D. Maha, Eur. J. Med. Chem., 38, 959 (2003).

    Article  Google Scholar 

  21. A. B. Adnan, M. A. A. Hayam, S. A. G. Yasser, E.-D. A. B. Alan, and B. Azza, Eur. J. Med. Chem., 43, 456 (2008).

    Article  Google Scholar 

  22. W. W. Wagnat and A. L. Nadia, J. Chilean Chem. Soc., 52, 1145 (2007).

    Google Scholar 

  23. D. Zainaba, L. Meryem, S. Abdelfatah, B. Abdelmejid, H. Mohammed, K. Said, and B. Mohammed, Arch. Pharm., 339, 291 (2006).

    Article  Google Scholar 

  24. I. Bouabdallah, L. A. M’Barek, A. Zyad, A. Ramdani, I. Zidane, and A. Melhaoui, Nat. Prod. Res., 20, 1024 (2006).

    Article  CAS  Google Scholar 

  25. A. Şener, E. Akbas, and M. K. Şener, Turkey J. Chem., 28, 271 (2004).

    Google Scholar 

  26. H. E. El Sayed, F. A. Kamal, A.-E. Salah, and B. Razika, J. Carbohydr. Chem., 26, 1 (2007).

    Article  Google Scholar 

  27. Q. Jairo, C. Debora, I. Braulio, A. Rodrigo, C. Silvia, N. Manuel, and C. Justo, J. Heterocycl. Chem., 45, 155 (2008).

    Article  Google Scholar 

  28. X. Deng and N. S. Mani, Org. Lett., 8, 3505 (2006).

    Article  CAS  Google Scholar 

  29. L. Pezdirc, V. Groselj, A. Meden, B. Stanovnik, and J. Svete, J. Heterocycl. Chem., 45, 181 (2008).

    Article  CAS  Google Scholar 

  30. P. Wang, Z. Xie, Z. Hong, J. Tang, O. Wong, C.-S. Lee, N. Wong, and S. Lee, J. Mat. Chem., 13, 1894 (2003).

    Article  CAS  Google Scholar 

  31. S. M. Allin, W. R. Bowman, M. R. J. Elsegood, V. Mckee, R. Karim, and S. S. Rahman, Tetrahedron, 61, 2689 (2005).

    Article  CAS  Google Scholar 

  32. C. A. Obafemi and W. Pfleiderer, Helv. Chim. Acta., 77, 1549 (1994).

    Article  CAS  Google Scholar 

  33. L. P. Carrod and F. D. Grady, Antibiotics and Chemotherapy, 3rd ed., Churchill Livingstone, Edinburgh, 1972, p. 477.

    Google Scholar 

  34. A. D. Russell and J. R. Furr, J. Appl. Bacteriol., 43, 253 (1977).

    CAS  Google Scholar 

  35. N. Rashed, A. M. El Massry, E.-S. H. El Ashry, A. Amer, and H. Zimmer, J. Heterocycl. Chem., 27, 691 (1990).

    Article  CAS  Google Scholar 

  36. G. W. H. Cheeseman and M. Rafiq, J. Chem. Soc., C, 452 (1971).

Download references

Author information

Authors and Affiliations

  1. Chemistry Department, College of Science and Technology, Covenant University, Canaanland, Km 10, Idiroko Road, P.M.B. 1023, Ota, Ogun State, Nigeria

    Olayinka O. Ajani, Craig A. Obafemi, Chinwe O. Ikpo & Kehinde O. Ogunniran

  2. Department of Chemistry, Faculty of Science, Obafemi Awolowo University, Ile-ife, Osun State, Nigeria

    Craig A. Obafemi

  3. Department of Biological Sciences, College of Science and Technology, Covenant University, Canaanland, Km 10, Idiroko Road, P.M.B. 1023, Ota, Ogun State, Nigeria

    Obinna C. Nwinyi

Authors
  1. Olayinka O. Ajani
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Craig A. Obafemi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Chinwe O. Ikpo
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kehinde O. Ogunniran
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. Obinna C. Nwinyi
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Olayinka O. Ajani.

Additional information

Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1703–1713, November, 2009.

Rights and permissions

Reprints and permissions

About this article

Cite this article

Ajani, O.O., Obafemi, C.A., Ikpo, C.O. et al. Microwave-assisted synthesis and antibacterial activity of some pyrazol-1-ylquinoxalin- 2(1H)-one derivatives. Chem Heterocycl Comp 45, 1370–1378 (2009). https://doi.org/10.1007/s10593-010-0435-z

Download citation

  • Received:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s10593-010-0435-z

Keywords

Search

Navigation