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Pyrazole Schiff bases cross-linked supramolecules: structural elucidation and antibacterial activity

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Abstract

Three pyrazole Schiff bases (E)-2-(((1H-pyrazol-3-yl)imino)methyl)-6-methoxyphenol (1), (Z)-N-(4-bromobenzylidene)-1H-pyrazol-3-amine (2), and (E)-2-(((1H-pyrazol-3-yl)imino) methyl)-4,6-dibromophenol (3) have been synthesized and characterized by elemental analyses, FT-IR, 1HNMR. The molecular structures were confirmed by X-ray structural studies, and investigated intermolecular interactions in building different supramolecular architectures. The title compounds are associated through hydrogen bonds, π-stacking interactions and further connected into hydrogen-bonded supramolecular layers and are responsible as well for the strengthening of the molecular assembly. In addition, the title compounds were also tested for their ability to inhibit the growth of C. albicans and Gram-negative bacteria. It was worthwhile to note that 1 and 3 could be used as potential antibacterial agents.

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References

  1. C.B. Aakeröy, N.R. Champnes, C. Janiak, CrystEngComm 12, 22 (2010)

    Article  Google Scholar 

  2. D. Braga, L. Brammer, N.R. Champness, CrystEngComm 7, 1 (2005)

    Article  CAS  Google Scholar 

  3. M. Dinca, J.R. Long, Angew. Chem., Int. Ed. 47, 6766 (2008)

    Article  CAS  Google Scholar 

  4. A.I. Kitaigorodskii, Molecular Crystals and Molecules (Academic Press, New York, 1973)

    Google Scholar 

  5. G.R. Desiraju, J.A.R.P. Sarma, Proc. Indian Acad. Sci. Chem. Sci. 96, 599 (1986)

    Article  CAS  Google Scholar 

  6. F.H. Allen, Acta Crystallogr. Sect. B Struct. Sci. 58, 380 (2002)

    Article  Google Scholar 

  7. M. Polito, E. D’Oria, L. Maini, P.G. Karamertzanis, F. Grepioni, D. Braga, S.L. Price, CrystEngComm 10, 1848 (2008)

    Article  CAS  Google Scholar 

  8. C. Janiak. J. Chem. Soc. Dalton Trans. 21, 3885–3896 (2000)

  9. H. Zhu, M. Ströbele, Z. Yu, Z. Wang, H.-J. Meyer, X. You, Inorg. Chem. Commun. 4, 577–581 (2001)

    Article  CAS  Google Scholar 

  10. M.J. MacLachlan, Pure Appl. Chem. 78, 873–888 (2006)

    Article  CAS  Google Scholar 

  11. Y.R. Li, C. Li, J.C. Liu, M. Guo, T.Y. Zhang, L.P. Sun, C.J. Zheng, H.R. Piao, Bioorg. Med. Chem. Lett. 25, 5052 (2015)

    Article  CAS  Google Scholar 

  12. J.X. Wang, Z.R. Zhu, F.Y. Bai, X.Y. Wang, X.X. Zhang, Y.H. Xing, Polyhedron 99, 59 (2015)

    Article  CAS  Google Scholar 

  13. E. Akbas, I. Berber, A. Sener, B. Hasanov, Il Farmaco 60, 23 (2005)

    Article  CAS  Google Scholar 

  14. G.M. Sheldrick, SHELXL97, Program for the refinement of crystal structures (University of Göttingen, Germany, 1997)

    Google Scholar 

  15. H.D. Flack, Acta Cryst. A39, 876 (1983)

    Article  CAS  Google Scholar 

  16. A.C. Cunha, V.F. Ferreira, A.K. Jordão, M.C.B.V. de Souza, S.M.S.V. Wardell, J.L. Wardell, P.A. Tan, R.P.A. Bettens, S.K. Seth, E. R. T. Tiekink, CrystEngComm 15, 4917 (2013)

    Article  CAS  Google Scholar 

  17. S.K. Seth, D. Sarkar, A. Roy, T. Kar, CrystEngComm 13, 6728–6741 (2011)

    Article  CAS  Google Scholar 

  18. S.K. Seth, D. Sarkar, T. Kar, CrystEngComm 13, 4528–4535 (2011)

    Article  CAS  Google Scholar 

  19. S.K. Seth, D. Sarkar, A.D. Jana, T. Kar, Cryst. Growth Des. 11, 4837–4849 (2011)

    Article  CAS  Google Scholar 

  20. J. Bernstein, R.E. Davis, L. Shimoni, N.L. Chang, Angew. Chem. Int. Ed. 34, 1555 (1995)

    Article  CAS  Google Scholar 

  21. I. Berber, C. Cokmus, E. Atalan, Microbiology 72, 54 (2003)

    Article  CAS  Google Scholar 

  22. L.A. Mitscher, S.P. Pillai, E.J. Gentry, D.M. Shankel, Med. Res. Rev. 19, 477 (1999)

    Article  CAS  Google Scholar 

  23. V. Lee, S.J. Hecker, Med. Res. Rev. 19, 521 (1999)

    Article  CAS  Google Scholar 

  24. E.V. Pimerova, E.V. Voronina, Pharm. Chem. J. 35, 18 (2001)

    Article  Google Scholar 

  25. V.A. Chornous, M.K. Bratenko, M.V. Vovk, I.I. Sidorchuk, Pharm. Chem. J. 35, 26 (2001)

    Article  Google Scholar 

Download references

Acknowledgements

We gratefully acknowledge the Key Research Project of Natural Science from Provincial Bureau of Education, Anhui, China (KJ2017A572), the National Natural Science Foundation of China (20801012), and the financial support from Jiangsu Ainaji Neoenergy Science and Technology Co., Ltd (8507040091).

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Correspondence to Chao Feng or Hong Zhao.

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Feng, C., Guo, JJ., Sun, LN. et al. Pyrazole Schiff bases cross-linked supramolecules: structural elucidation and antibacterial activity. J IRAN CHEM SOC 15, 2871–2876 (2018). https://doi.org/10.1007/s13738-018-1473-1

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  • DOI: https://doi.org/10.1007/s13738-018-1473-1

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