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SBA-Pr-SO3H-catalyzed synthesis of bispyrazole compounds as anti-bacterial agents and inhibitors of phosphorylated RET tyrosine kinase

  • Ghodsi Mohammadi ZiaraniEmail author
  • Fatemeh Saidian
  • Parisa Gholamzadeh
  • Alireza Badiei
  • Jahan B. Ghasemi
  • Elham Aghaee
  • Ali Abolhasani Soorki
Original Paper
  • 15 Downloads

Abstract

Pyrazolone was prepared through the reaction of ethyl acetoacetate and hydrazine hydrate in EtOH at room temperature. Then, bispyrazole derivatives, as attractive biologically active compounds, were synthesized by reacting two equivalents of prepared pyrazolone and one equivalent of aldehyde in the presence of SBA-Pr-SO3H under solvent-free condition at 120 °C. The reaction time was short (3–6 min), while the products’ yield was high (85–97%). Discovery Studio 2.5 (Accelrys Inc, San Diego, CA, USA) was employed to dock the compounds to protein. Molecular docking (GOLD method) studies suggested that pyrazoles bind efficiently to RET kinase. Next, biological activities of the bispyrazoles were tested against some Gram-positive and Gram-negative bacteria and for antifungal activity via the disc-diffusion method. All compounds showed no significant anti-bacterial activities, but two of them showed good activities against Candida albicans.

Graphical abstract

Keywords

Bispyrazole Green synthesis Heterogeneous catalyst Antifungal activity GOLD method 

Notes

Acknowledgements

We gratefully acknowledge for the financial support from the Research Council of Alzahra University and the University of Tehran.

Supplementary material

13738_2019_1618_MOESM1_ESM.doc (601 kb)
Supplementary material 1 (DOC 600 KB)

References

  1. 1.
    S.K. Tambe, N.S. Dighe, S.R. Pattan, M.S. Kedar, D.S. Musmade, M.N.S. Dighe, Pharmacologyonline. 2, 5 (2010)Google Scholar
  2. 2.
    F. Al’-Assar, K.N. Zelenin, E.E. Lesiovskaya, I.P. Bezhan, B.A. Chakchir, Pharm. Chem. J. 36, 598 (2002)CrossRefGoogle Scholar
  3. 3.
    H. Naito, S. Ohsuki, M. Sugimori, R. Atsumi, M. Minami, Y. Nakamura, M. Ishii, K. Hirotani, E. Kumazawa, A. Ejima, Chem. Pharm. Bull. 50, 453 (2002)CrossRefGoogle Scholar
  4. 4.
    N.M. Abunada, H.M. Hassaneen, N.G. Kandile, O.A. Miqdad, Molecules. 13, 1501 (2008)CrossRefGoogle Scholar
  5. 5.
    A. Geronikaki, E. Babaev, J. Dearden, W. Dehaen, D. Filimonov, I. Galaeva, V. Krajneva, A. Lagunin, F. Macaev, G. Molodavkin, Bioorg. Med. Chem. 12, 6559 (2004)CrossRefGoogle Scholar
  6. 6.
    S.J. Vaghasiya, D.K. Dodiya, A.R. Trivedi, V.H. Shah, Arkivoc. xii, 1 (2008)Google Scholar
  7. 7.
    V. Kumar, K. Kaur, G.K. Gupta, A.K. Sharma, Eur. J. Med. Chem. 69, 735 (2013)CrossRefGoogle Scholar
  8. 8.
    E.G. Brown, K.A.M. Flayeh, J.R. Gallon, Phytochemistry. 21, 863 (1982)CrossRefGoogle Scholar
  9. 9.
    G. Mohammadi Ziarani, N. Lashgari, A. Badiei, J. Mol. Catal. A Chem. 397, 166 (2015)CrossRefGoogle Scholar
  10. 10.
    G. Mohammadi Ziarani, S. Ghorbi, P. Gholamzadeh, A. Badiei, Iran. J. Catal. 6, 229 (2016)Google Scholar
  11. 11.
    S. Rostamnia, E. Doustkhah, Synlett. 26, 1345 (2015)CrossRefGoogle Scholar
  12. 12.
    P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, A.A. Soorki, N. Lashgari, Res. Chem. Intermed. 39, 3925 (2013)CrossRefGoogle Scholar
  13. 13.
    J.J. Gabla, D.R. Lathiya, A.A. Revawala, K.C. Maheria, Res. Chem. Intermed. (2018).  https://doi.org/10.1007/s11164-018-3707-3 Google Scholar
  14. 14.
    G. Mohammadi Ziarani, S. Faramarzi, N. Lashgari, A. Badiei, J. Iran. Chem. Soc. 11, 701 (2014)CrossRefGoogle Scholar
  15. 15.
    G. Mohammadi Ziarani, P. Gholamzadeh, A. Badiei, S. Asadi, A.A. Soorki, J. Chil. Chem. Soc. 60, 2975 (2015)CrossRefGoogle Scholar
  16. 16.
    S.Y. Afsar, G. Mohammadi Ziarani, H. Mollabagher, P. Gholamzadeh, A. Badiei, A.A. Soorki, J. Iran. Chem. Soc. 14, 577 (2017)CrossRefGoogle Scholar
  17. 17.
    P. Gholamzadeh, G. Mohammadi Ziarani, A. Badiei, J. Chil. Chem. Soc. 61, 2935 (2016)CrossRefGoogle Scholar
  18. 18.
    B. Karimi, M. Vafaeezadeh, RSC Adv. 3, 23207 (2013)CrossRefGoogle Scholar
  19. 19.
    F.A. Momany, R. Rone, J. Comput. Chem. 13, 888 (1992)CrossRefGoogle Scholar
  20. 20.
    A. Politi, S. Durdagi, P. Moutevelis-Minakakis, G. Kokotos, T. Mavromoustakos, J. Mol. Graph. Model. 29, 425 (2010)CrossRefGoogle Scholar
  21. 21.
    G. Mohammadi Ziarani, R. Moradi, N. Lashgari, A. Badiei, A.A. Soorki, Quim. Nova 38, 1167 (2015)Google Scholar
  22. 22.
    A. Vafaee, A. Davoodnia, M. Pordel, Res. Chem. Intermed. 41, 8343 (2015)CrossRefGoogle Scholar
  23. 23.
    W. Wang, S.X. Wang, X.Y. Qin, J.T. Li, Synth. Commun. 35, 1263 (2005)CrossRefGoogle Scholar
  24. 24.
    C. Yang, W.-Q. Su, D.-Z. Xu, RSC Adv. 6, 99656 (2016)CrossRefGoogle Scholar
  25. 25.
    N.G. Khaligh, S.B.A. Hamid, S.J.J. Titinchi, Chin. Chem. Lett. 27, 104 (2016)CrossRefGoogle Scholar
  26. 26.
    Z. Zhou, Y. Zhang, J. Chil. Chem. Soc. 60, 2992 (2015)CrossRefGoogle Scholar
  27. 27.
    J. Safaei-Ghomi, B. Khojastehbakht-Koopaei, S. Zahedi, Chem. Heterocycl. Compd. 51, 34 (2015)CrossRefGoogle Scholar
  28. 28.
    R. Ramesh, N. Nagasundaram, D. Meignanasundar, P. Vadivel, A. Lalitha, Res. Chem. Intermed. 43, 1767 (2017)CrossRefGoogle Scholar
  29. 29.
    E. Soleimani, S. Ghorbani, M. Taran, A. Sarvary, C. R. Chim. 15, 955 (2012)CrossRefGoogle Scholar

Copyright information

© Iranian Chemical Society 2019

Authors and Affiliations

  1. 1.Department of ChemistryAlzahra UniversityTehranIran
  2. 2.School of Chemistry, College of ScienceUniversity of TehranTehranIran
  3. 3.Research Institute of Applied Sciences, ACECRShahid Beheshti UniversityTehranIran

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