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

M. A. Uvarova; Уварова М. А.; M. V. Novikova; Новикова М. В.; V. A. Eliseenkova; Елисеенкова В. А.; D. E. Baravikov; Баравиков Д. Е.; F. M. Dolgushin; Долгушин Ф. М.; O. B. Bekker; Беккер О. Б.; E. V. Fatushina; Фатюшина Е. В.; M. A. Kiskin; Кискин М. А.; I. L. Eremenko; Еременко И. Л.; I. A. Lutsenko; Луценко И. А.

doi:10.31857/S0132344X23600200

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

Authors: Uvarova M.A.¹, Novikova M.V.¹^,2, Eliseenkova V.A.³, Baravikov D.E.¹^,4, Dolgushin F.M.¹, Bekker O.B.⁵, Fatushina E.V.¹, Kiskin M.A.¹, Eremenko I.L.¹, Lutsenko I.A.¹
Affiliations:
1. Kurnakov Institute of General and Inorganic Chemistry, Russian Academy of Sciences, Moscow, Russia
2. Moscow Institute of Physics and Technology, Moscow, Russia
3. School no. 1553 named after Vernadsky, Moscow, Russia
4. Mendeleev University of Chemical Technology of Russia, Moscow, Russia
5. Vavilov Institute of General Genetics, Russian Academy of Sciences, Moscow, Russia
Issue: Vol 49, No 10 (2023)
Pages: 651-658
Section: Articles
URL: https://rjsvd.com/0132-344X/article/view/667476
DOI: https://doi.org/10.31857/S0132344X23600200
EDN: https://elibrary.ru/OCUHPJ
ID: 667476

Cite item

Full Text

Open Access
Restricted Access

Access granted
Restricted Access

Subscription or Fee Access

Abstract
About the authors
References
Supplementary files
Statistics

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 I–III 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 I–III was determined in relation to the non-pathogenic Mycolicibacterium smegmatis.

Keywords

copper(II) and zinc(II) complexes, 3, 5-dimethylpyrazole, 3-furancarboxylic acid, 2-thiophenecarboxylic acid, crystal structure, biological activity

References

Goodwin L. // Trop. Med. Hyg. 1995. V. 89. № 3. P. 339.
Ngwane A.H., Petersen R.D., Baker B. et al. // IUBMB Life. 2019. V. 71. № 5. P. 532.
Chen Z.F., Orvig C., Liang H. // Curr. Top. Med. Chem. 2017. V. 17. № 28. P. 3131.
Chaudhary A., Jha K., Kumar S. // J. Adv. Res. 2012. V. 3. № 3. P. 3.
Lukevits É., Demicheva L. // Chem. Heterocycl. Co-mpd. 1993. V. 29. P. 243.
Машковский М.Д. Лекарственные средства. М.: Медицина. 2000. Т. 1. 736 с.
Kuchtanin V., Moncol J., Mroziński J. // Polyhedron. 2013. V. 50. № 1. P. 546.
Panagoulis D.E. Pontiki E., Skeva C. et al. // Inorg. Chem. 2007. V. 101. P. 623.
Zheng X.F., Zhou Y.X., Wan X.S. // Inorg. Met.-Org. Nano-Met. Chem. 2007. V. 37. P. 255.
Horn E., Kurosawa K., Tamura H., Nakahodo T. // Z. Krist. New. Cryst. Struct. 2001. V. 216. P. 77.
Melnic S., Prodius D., Stoeckli-Evans H. et al. // Eur. J. Med. Chem. 2010. V. 45. P. 1465.
Луценко И.А., Баравиков Д.Е., Кискин М.А. и др. // Коорд. химия. 2020. Т. 46. № 6. С. 366 (Lutsenko I.A., Kiskin M.A., Nelyubina Y.V. et al. // Russ. J. Coord. Chem. 2020. Т. 46. № 6. P. 411). https://doi.org/10.1134/S1070328420060056
Луценко И.А., Ямбулатов Д.С., Кискин М.А. и др. // Коорд. химия. 2020. Т. 46. № 12. С. 715 (Lutsenko I.A., Yambulatov D.S., Kiskin M.A. // Russ. J. Coord. Chem. 2020. Т. 46. № 12. P. 787). https://doi.org/10.1134/S1070328420120040
Lutsenko I.A., Yambulatov D.S., Kiskin M.A. et al. // ChemSelect. 2020. V. 5. № 38. P. 11837.
Луценко И.А., Кискин М.А., Кошенскова К.А. и др. // Изв. АН. Сер. хим. 2021. № 3. С. 463 (Lutsenko I.A., Kiskin M.A., Koshenskova K.A. et al. // Russ. Chem. Bull. 2021. V. 70. № 3. P. 463). https://doi.org/10.1007/s11172-021-3109-3
Uvarova M.A., Lutsenko I.A., Kiskin M.A. et al. // Polyhedron. 2021. V. 203. P. 115241. https://doi.org/10.1016/j.poly.2021.115241
Луценко И.А., Никифорова М.Е., Кошенскова К.А. и др. // Коорд. химия. 2022. Т. 48. № 2. С. 83 (Lutsenko I.A., Nikiforova M.E., Koshenskova K.A. et.al. // Russ. J. Coord. Chem. 2021. V. 47. P. 879). https://doi.org/10.1134/S1070328421350013
Lutsenko I.A., Baravikov D.E., Koshenskova K.A. et al. // RSC Adv. 2022. V. 12. P. 5173.
Кошенскова К.А., Луценко И.А., Нелюбина Ю.В. и др. // Журн. неорган. химии. 2022. Т. 67. № 10. С. 1398 (Koshenskova K.A., Lutsenko I.A., Nelyubina Y.V. et al. // Russ. J. Inorg. Chem. V. 67. № 10. P. 1545). https://doi.org/10.1134/S003602362270005X
Ansari A., Ali A., Asif M., Shamsuzzaman S. // New J. Chem. 2017. V. 41. № 1. P. 16.
Xu Z., Gao C., Ren Q.C., Song X.F. et al. // Eur. J. Med. Chem. 2017. V. 139. P. 429.
Karrouchi K., Radi S., Ramli Y. et al. // Molecules. 2018. V. 23. № 1. P. 134.
Azam M., Mohammad Wabaidur S., Alam M. // Polyhedron. 2021. V. 195. P. 114991.
Solanki A., Kumar S.B., Doshi A.A., Ratna Prabha C. // Polyhedron. 2013. V. 63. P. 147.
Уварова М.А., Нефедов С.Е. // Коорд. химия. 2020. Т. 46. № 2. С. 117 (Uvarova M.A., Nefedov S.E. // Russ. J. Coord. Chem. 2020. V. 46. № 2. P. 125). https://doi.org/10.1134/S1070328420020062
Уварова М.А., Нефедов С.Е. // Журн. неорган. химии. 2015. Т. 60. № 9. С. 1181 (Uvarova M.A., Nefedov S.E. // Russ. J. Inorg. Chem. 2015. V. 60. № 9. P. 1074). https://doi.org/10.1134/S003602361509020X
Уварова М.А., Кушан Е.В., Нефедов С.Е. // Журн. неорган. химии. 2012. Т. 57. № 5. С. 744 (Uvarova M.A., Kushan E.V., Nefedov S.E. // Russ. J. Inorg. Chem. 2012. V. 57. № 5. С. 676). https://doi.org/10.1134/S0036023612050245
Уварова М.А., Нефедов С.Е. // Коорд. химия. 2022. Т. 48. № 9. С. 543 (Uvarova M.A., Nefedov S.E. // Russ. J. Coord. Chem. 2022. V. 48. P. 565). https://doi.org/10.1134/S107032842209007X
Uvarova M.A., Nefedov S.E. // Russ. J. Coord. Chem. 2022. T. 48. № 12. C. 909.
Yuan Lu, Weiqiang Xu, Kaikai Hu et al. // Polyhedron. 2019. V. 159. P. 408.
Krause L., Herbst-Irmer R., Sheldrick G.M., Stalke D. // J. Appl. Cryst. 2015. V. 48. P. 3.
Sheldrick G.M. // Acta Crystallogr. A. 2015. V. 71. P. 3.
Dolomanov O.V., Bourhis L.J., Gildea R.J et al. // J. Ap-pl. Cryst. 2009. V. 42. P. 339.
Kaikai H., Shouwen J., Zuoran Xie, Ming G. et al. // Polyhedron. 2018. V. 139. P. 17.
Ramon-García S., Ng C., Anderson H. et al. // Antimicrob. Agents Chemother. 2011. V. 8. P. 3861.
Bekker O.B., Sokolov D.N., Luzina O.A. et al. // Med. Chem. Res. 2015. V. 24. P. 2926.