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Copper(II) and Zinc(II) Complexes with Heterocyclic Acid Anions and 3,5-Dimethylpyrazole: Synthesis, Structure, and Biological Properties

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Abstract

The reaction of copper(II) and zinc(II) acetates with 3-furancarboxylic (HFur) and 2-thiophenecarboxylic (HTph) acids with subsequent addition of 3,5-dimethylpyrazole (HDmpz) gave mononuclear complexes [M(L)2(HDmpz)2] (M = Cu(II), L = Fur (I), Tph (II); Zn(II), L = Fur (III)). The structures of compounds IIII were determined by X-ray diffraction. According to X-ray diffraction data, I and II are isostructural: the central Cu(II) atom occurs in a square planar environment formed by two oxygen atoms of carboxylate anions and HDmpz nitrogen atoms; in III, the Zn atom is in the tetrahedral environment of two furoate anions and HDmpz molecules, thus forming the {MO2N2} groups. The complexes are additionally stabilized in the crystal by inter- (I and II) and intramolecular (III) hydrogen bonds. The biological activity of IIII was determined in relation to the non-pathogenic Mycolicibacterium smegmatis.

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REFERENCES

  1. Goodwin, L., Trop. Med. Hyg., 1995, vol. 89, no. 3, p. 339.

    Article  CAS  Google Scholar 

  2. Ngwane, A.H., Petersen, R.D., Baker, B., et al., IUBMB Life, 2019, vol. 71, no. 5, p. 532.

    Article  CAS  PubMed  Google Scholar 

  3. Chen, Z.F., Orvig, C., and Liang, H., Curr. Top. Med. Chem., 2017, vol. 17, no. 28, p. 3131.

    CAS  PubMed  Google Scholar 

  4. Chaudhary, A., Jha, K., and Kumar, S., J. Adv. Res., 2012, vol. 3, no. 3, p. 3.

    CAS  Google Scholar 

  5. Lukevits, É. and Demicheva, L., Chem. Heterocycl. Compd., 1993, vol. 29, p. 243.

    Article  Google Scholar 

  6. Mashkovskii, M.D., Lekarstvennye sredstva (Pharmaceutical Products), Moscow: Meditsina, 2000, vol. 1.

  7. Kuchtanin, V., Moncol, J., and Mroziński, J., Polyhedron, 2013, vol. 50, no. 1, p. 546.

    Article  CAS  Google Scholar 

  8. Panagoulis, D.E., Pontiki, E., Skeva, C., et al., Inorg. Chem., 2007, vol. 101, p. 623.

    CAS  Google Scholar 

  9. Zheng, X.F., Zhou, Y.X., and Wan, X.S., Inorg. Met.-Org. Nano-Met. Chem., 2007, vol. 37, p. 255.

    CAS  Google Scholar 

  10. Horn, E., Kurosawa, K., Tamura, H., and Nakahodo, T., Z. Krist. New. Cryst. Struct., 2001, vol. 216, p. 77.

    CAS  Google Scholar 

  11. Melnic, S., Prodius, D., Stoeckli-Evans, H., et al., Eur. J. Med. Chem., 2010, vol. 45, p. 1465.

    Article  CAS  PubMed  Google Scholar 

  12. Lutsenko, I.A., Kiskin, M.A., Nelyubina, Y.V., et al., Russ. J. Coord. Chem., 2020, vol. 46, no. 6, p. 411 https://doi.org/10.1134/S1070328420060056

    Article  CAS  Google Scholar 

  13. Lutsenko, I.A., Yambulatov, D.S., and Kiskin, M.A., Russ. J. Coord. Chem., 2020, vol. 46, no. 12, p. 787. https://doi.org/10.1134/S1070328420120040

    Article  CAS  Google Scholar 

  14. Lutsenko, I.A., Yambulatov, D.S., Kiskin, M.A., et al., ChemSelect, 2020, vol. 5, no. 38, p. 11837.

    CAS  Google Scholar 

  15. Lutsenko, I.A., Kiskin, M.A., Koshenskova, K.A., et al., Russ. Chem. Bull., 2021, vol. 70, no. 3, p. 463. https://doi.org/10.1007/s11172-021-3109-3

    Article  CAS  Google Scholar 

  16. Uvarova, M.A., Lutsenko, I.A., Kiskin, M.A., et al., Polyhedron, 2021, vol. 203, p. 115241. https://doi.org/10.1016/j.poly.2021.115241

    Article  CAS  Google Scholar 

  17. Lutsenko, I.A., Nikiforova, M.E., Koshenskova, K.A., et al., Russ. J. Coord. Chem., 2021, vol. 47, p. 879. https://doi.org/10.1134/S1070328421350013

    Article  Google Scholar 

  18. Lutsenko, I.A., Baravikov, D.E., Koshenskova, K.A., et al., RSC Adv., 2022, vol. 12, p. 5173.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  19. Koshenskova, K.A., Lutsenko, I.A., Nelyubina, Y.V., et al., Russ. J. Inorg. Chem., 2022, vol. 67, no. 10, p. 1545. https://doi.org/10.1134/S003602362270005X

    Article  CAS  Google Scholar 

  20. Ansari, A., Ali, A., Asif, M., and Shamsuzzaman, S., New J. Chem., 2017, vol. 41, no. 1, p. 16.

    Article  CAS  Google Scholar 

  21. Xu, Z., Gao, C., Ren, Q.C., Song, X.F., et al., Eur. J. Med. Chem., 2017, vol. 139, p. 429.

    Article  CAS  PubMed  Google Scholar 

  22. Karrouchi, K., Radi, S., Ramli, Y., et al., Molecules, 2018, vol. 23, no. 1, p. 134.

    Article  PubMed  PubMed Central  Google Scholar 

  23. Azam, M., Mohammad Wabaidur, S., and Alam, M., Polyhedron, 2021, vol. 195, p. 114991.

    Article  CAS  Google Scholar 

  24. Solanki, A., Kumar, S.B., Doshi, A.A., and Ratna Prabha, C., Polyhedron, 2013, vol. 63, p. 147.

    Article  CAS  Google Scholar 

  25. Uvarova, M.A. and Nefedov, S.E., Russ. J. Coord. Chem., 2020, vol. 46, no. 2, p. 125. https://doi.org/10.1134/S1070328420020062

  26. Uvarova, M.A. and Nefedov, S.E., Russ. J. Inorg. Chem., 2015, vol. 60, no. 9, p. 1074. https://doi.org/10.1134/S003602361509020X

  27. Uvarova, M.A., Kushan, E.V., and Nefedov, S.E., Russ. J. Inorg. Chem., 2012, vol. 57, no. 5, p. 676. https://doi.org/10.1134/S0036023612050245

  28. Uvarova, M.A. and Nefedov, S.E., Russ. J. Coord. Chem., 2022, vol. 48, p. 565. https://doi.org/10.1134/S107032842209007X

    Article  CAS  Google Scholar 

  29. Uvarova, M.A. and Nefedov, S.E., Russ. J. Coord. Chem., 2022, vol. 48, no. 12, p. 909.

    Article  CAS  Google Scholar 

  30. Yuan Lu, Weiqiang Xu, Kaikai Hu, et al., Polyhedron, 2019, vol. 159, p. 408.

    Article  CAS  Google Scholar 

  31. Krause, L., Herbst-Irmer, R., Sheldrick, G.M., and Stalke, D., J. Appl. Crystallogr., 2015, vol. 48, p. 3.

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  32. Sheldrick, G.M., Acta Crystallogr., Sect. A: Found. Adv., 2015, vol. 71, p. 3.

    Article  Google Scholar 

  33. Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., et al., J. Appl. Crystallogr., 2009, vol. 42, p. 339.

    Article  CAS  Google Scholar 

  34. Kaikai, H., Shouwen, J., Zuoran, **e., Ming, G., et al., Polyhedron, 2018, vol. 139, p. 17.

    Article  Google Scholar 

  35. Ramon-García, S., Ng, C., Anderson, H., et al., Antimicrob. Agents Chemother., 2011, vol. 8, p. 3861.

    Article  Google Scholar 

  36. Bekker, O.B., Sokolov, D.N., Luzina, O.A., et al., Med. Chem. Res., 2015, vol. 24, p. 2926.

    Article  CAS  Google Scholar 

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ACKNOWLEDGMENTS

X-ray diffraction, IR spectroscopy, and C,H,N,S analysis were performed using equipment of the Center for Collective Use of Physical Investigation Methods of the Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, supported by the state assignment for the Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, in the field of fundamental research.

Funding

This study was supported by the Ministry of Education and Science of the Russian Federation within the framework of the state assignment for the Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences.

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Correspondence to M. A. Uvarova.

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Translated by Z. Svitanko

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Uvarova, M.A., Novikova, M.V., Eliseenkova, V.A. et al. Copper(II) and Zinc(II) Complexes with Heterocyclic Acid Anions and 3,5-Dimethylpyrazole: Synthesis, Structure, and Biological Properties. Russ J Coord Chem 49, 680–687 (2023). https://doi.org/10.1134/S1070328423600419

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