Abstract
2-Oxopropanoic acid reacts in ethanol with N-(prop-2-en-1-yl)hydrazinecarbothioamide in a 1 : 1 mole ratio to form thiosemicarbazone H2L. Coordination compounds Cu(HL)X [X = Cl–, Br–, NO3–], Cu(H2O)(L), Ni(HL)2, Co(HL)2X [X = Cl–, Br–], and Fe(HL)2X [X = NO3–, Br–] are formed in the reactions of H2L with copper(II), nickel(II), cobalt(II), and iron(III) salts. The reactions of Cu(H2O)(L) with imidazole (Im) and 3,4-dimethylpyridine (3,4-Lut) result in mixed-ligand complexes Cu(A)(L) [A = Im, 3,4-Lut]. The structures of two copper complexes were determined by single crystal X-ray diffraction analysis. The synthesized complexes exhibit selective antimicrobial and antifungal activity in the concentration range of 15.62–1000 μg/mL. The introduction of amines into the inner sphere of copper complexes leads to an increase in the antimicrobial activity.
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REFERENCES
Beraldo, H. and Gambino, D., Mini Rev. Med. Chem., 2004, vol. 4, no. 1, p. 31. https://doi.org/10.2174/1389557043487484
Gulea, A.P., Graur, V.O., Chumakov, Yu.M., Petrenko, P.A., Balan, G.G., Burduniuc, O.S., Tsapkov, V.I., and Rudic, V.F., Russ. J. Gen. Chem., 2019, vol. 89, no. 5, p. 953. https://doi.org/10.1134/S1070363219050153
Pahontu, E., Fala, V., Gulea, A., Poirier, D., Tapcov, V., and Rosu, T., Molecules, 2013, vol. 18, no. 8, p. 8812. https://doi.org/10.3390/molecules18088812
Lukmantara, A.Y., Kalinowski, D., Kumar, N., and Richardson, D.R., J. Inorg. Biochem., 2014, vol. 141, p. 43. https://doi.org/10.1016/j.jinorgbio.2014.07.020
Diaz, A., Cao, R., and Garcia, A., Monatsh. Chem., 1994, vol. 125, nos. 8–9, p. 823. https://doi.org/10.1007/BF00812694
Pathan, A.H., Bakale, R.P., Naik, G.N., Frampton, C.S., and Gudasi, K.B., Polyhedron, 2012, vol. 34, no. 1, p. 149. https://doi.org/10.1016/j.poly.2011.12.033
Pathan, A.H., Ramesh, A.K., Bakale, R.P., Naik, G.N., Rohit Kumar, H.G., Frampton, C.S., Advi Rao, G.M., and Gudasi, K.B., Inorg. Chim. Acta, 2015, vol. 430, p. 216. https://doi.org/10.1016/j.ica.2015.03.013
Baldini, M., Belicchi-Ferrari, M., Bisceglie, F., Dall’Aglio, P. P., Pelosi, G., Pinelli, S., and Tarasconi, P., Inorg. Chem., 2004, vol. 43, no. 22. P. 7170. https://doi.org/10.1021/ic049883b
Pelosi, G., Open Crystallogr. J., 2010, vol. 3, p. 16. https://doi.org/10.2174/1874846501003010016
Prisakar’, V.I., Tsapkov, V.I., Buracheeva, S.A., Byrke, M.S., and Gulya, A.P., Pharm. Chem. J., 2005, vol. 39, no. 6, p. 313. https://doi.org/10.1007/s11094-005-0142-8
Samus’, N.M., Gulya, A.P., Tsapkov, V.I., Chumakov, Y.M., and Roshu, T., Russ. J. Gen. Chem., 2006, vol. 76, no. 7, p. 1100. https://doi.org/10.1134/s1070363206070164
Belicchi-Ferrari, M., Bisceglie, F., Buluggiu, E., Pelosi, G., and Tarasconi, P., Polyhedron, 2010, vol. 29, no. 10, p. 2134. https://doi.org/10.1016/j.poly.2010.04.009
Belicchi-Ferrari, M., Bisceglie, F., Buluggiu, E., Pelosi, G., and Tarasconi, P., Polyhedron, 2009, vol. 28, no. 6, p. 1160. https://doi.org/10.1016/j.poly.2009.01.013
Allen, F.H., Acta Crystallogr. B, 2002, vol. 58, p. 380. https://doi.org/10.1107/S0108768102003890
CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.34.76, 2003.
Sheldrich, G.M., Acta Crystallogr. (А), 2008, vol. 64, p. 112. https://doi.org/10.1107/S0108767307043930
Gulea, A., Poirier, D., Roy, J., Stavila, V., Bulimestru, I., Tapcov, V., and Popovschi, L, J. Enzyme Inhib. Med. Chem., 2008, vol. 23, no. 6, p. 806. https://doi.org/10.1080/14756360701743002
Pahontu, E., Usataia, I., Graur, V., Chumakov, Yu., Petrenko, P., Gudumac, V., and Gulea, A., Appl. Organometal. Chem., 2018, vol. 32, no. 12, p. e4544. https://doi.org/10.1002/aoc.4544
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The work was carried out within the framework of the State program of the Republic of Moldova (project 20.80009.5007.10).
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Gulea, А.P., Graur, V.О., Diurici, E.C. et al. Synthesis, Structure, and Biological Activity of Copper(II), Nickel(II), Cobalt(III), and Iron(III) Coordination Compounds with 2-{2-[(Prop-2-en-1-yl)carbamothioyl]hydrazinylidene}propanoic Acid. Russ J Gen Chem 90, 2120–2127 (2020). https://doi.org/10.1134/S107036322011016X
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DOI: https://doi.org/10.1134/S107036322011016X