Synthesis, Structure, and Biological Activity of Copper(II), Nickel(II), Cobalt(III), and Iron(III) Coordination Compoun
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hesis, 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 А. P. Guleaa, V. О. Graura,*, E. C. Diuricia, Ia. I. Ulchinaa, P. N. Bouroshb, G. G. Balanc, O. S. Burduniucc,d, V. I. Tsapkova, and V. F. Rudice a State
University of Moldova, Chisinau, MD-2009 Moldova of Applied Physics, Chisinau, MD-2028 Moldova c State University of Medicine and Pharmacy “Nicolae Testemitanu,” Chisinau, MD-2001 Moldova d National Agency of Public Health, Chisinau, MD-2028 Moldova e Institute of Microbiology and Biotechnology of Academy of Sciences of Moldova, Chisinau, MD-2028 Moldova *e-mail: [email protected] b Institute
Received June 26, 2020; revised June 26, 2020; accepted July 16, 2020
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. Keywords: coordination compounds, pyruvic acid 4-allylthiosemicarbazone, antimicrobial activity, antifungal activity
DOI: 10.1134/S107036322011016X Thiosemicarbazones and coordination compounds of transition metals with them are an important class of biologically active compounds [1–4]. The introduction of various substituents in the composition of thiosemicarbazones leads to a change in the mode of their coordination to the central metal atom, affects their biological activity, and increases the selectivity of their action. Previously, the coordination compounds of thiosemicarbazones of oxocarboxylic acids and their derivatives were found to have antimicrobial, antifungal [5, 6] and anticancer [7, 8] properties. Since the biological activity of such substances is often consistent with their structure [9], the introduction of amines into the inner sphere of copper complexes can lead to changes in their biological properties [3, 10, 11]. We have synthesized and studied new coordination compounds of copper(II), nickel(II), cobalt(III), and
iron(III) with 2-{2-[(prop-2-en-1-yl)carbamothioyl]hydrazinylidene}propanoic acid (H2L, Scheme 1). Thiosemicarbazone H 2 L was obtained by the reaction of N-(prop-2-en-1-yl)hydrazinecarbothioamide (4-allylthiosemicarbazide) with 2-oxopropanoic acid (pyruvic acid), taken in a molar ratio of 1 : 1, in ethanol. Its structure was confirm
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