2. Articole
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Item Synthesis and biological activity of n-(4-methoxyphenyl)-2-oxopropanamide 4-phenylthiosemicarbazone and its copper(II) complexes [Articol](CEP USM, 2024) Graur, Ianina; Usataia, Irina; Graur, Vasilii; Tsapkov, Victor; Gulea, Aurelian; Garbuz, Olga; Balan, GretaThe new N-(4-methoxyphenyl)-2-oxopropanamide 4-phenylthiosemicarbazone (HL) and its 5 copper(II) coordination compounds [Cu(L)X] (X = Cl- (I); Br- (II); NO3- (III); CH3COO- (IV); Cl2CHCOO- (V)) have been synthesized and characterized by elemental analysis, FTIR and NMR spectra. Coordination of 4-phenylthiosemicarbazone HL with the copper(II) atom led to increased antibacterial activity against Staphylococcus aureus and Bacillus cereus. Non-coordinated 4-phenylthiosemicarbazone (HL) showed the highest activity in relation to ABTS•+ cation radicals; its activity is close to that of Trolox, which is used in medicine. The antibacterial and antioxidant activities of the synthesized complexes are influenced by the nature of the acidic residue in their composition.Item Synthesis and biotechnological study of ethyl 2-((E)-2-((E) phenylallylidene) hydrazinecarbothioamido) acetate [Articol](CEP USM, 2024) Ciursin, Andrei; Trofim, Alina; Rusnac, RomanThe quality and length of human life is directly related to the development of medicine, in particular drugs. The modern world is constantly in the process of developing new, more effective drugs. Thiosemicarbazones may be one of the promising solutions. Despite their outstanding biological activities, many of them are toxic and cannot be used as medicines. The solution may be thiosemicarbazones, which are based on natural substances. This is expected to signifcantly reduce toxicity without impairing the biological activity of the substances. In this regard, for this work, a thiosemicarbazone was synthesized, which is based on two natural substances, glycine and cinnamaldehyde. To test the toxicity of this substance, some strains of cyanobacteria were used in this article. In addition to the lack of toxicity to these microorganisms, the synthesized thiosemicarbazone had a biostimulating effect.Item Synthesis, characterization, andbiological properties of the copper(II) complexes with novellig and: N-[4-({2-[1-(pyridin2-yl)ethylidene] hydrazinecarbothioyl}amino) phenyl] acetamide [Articol](2023) Rusnac, Roman; Garbuz, Olga; Ciumacov, Iurie; Țapcov, Victor; Hureau, Christelle; Istrati, Dorin; Gulea, AurelianFor the first time, a thiosemicarbazone-type ligand containing a paracetamol structural unit was synthesized. Five new coordination compounds based on copper(II) salts: [Cu(L)CH3COO] (1), [{Cu(L)Cl}2]·H2O (2), [Cu(L)H2O·DMF]NO3 (3), [Cu(L)Br] (4), [Cu(L)H2O]ClO4 (5), were obtained, where HL is N-[4-({2-[1-(pyridin-2-yl)ethylidene]hydrazinecarbothioyl}amino)phenyl]acetamide. The new HL was characterized by NMR, FTIR, spectroscopy, and X-ray crystallography. All copper(II) coordination compounds were characterized by elemental analysis, FTIR, EPR spectroscopy, and molar electrical conductivity. Furthermore, single crystal X-ray diffraction analysis elucidated the structures of thiosemicarbazone HL as well as complexes 1–3. All compounds were tested for antimicrobial, antifungal, and antioxidant activities, and their toxicity to Daphnia magna was studied. Biological evaluation has revealed that most of the synthesized compounds demonstrate promising antibacterial, antifungal, and antioxidant activities. In many cases, their antibacterial/antifungal activity is comparable to that of certain drugs used in medicine for these purposes, and in some cases, even surpasses them. HL and complexes 2–5 exhibit antioxidant activity that surpasses that of Trolox. Furthermore, HL and complex 2 display virtually no toxicity to D. magna.Item INTRODUCING N-HETEROAROMATIC BASES INTO COPPER(II) THIOSEMICARBAZON COMPLEXES: A WAY TO CHANGE THEIR BIOLOGICAL ACTIVITY(2022) Ulchina, Ianina; Graur, Vasilii; Țapcov, Victor; Ciumacov, Iurie; Garbuz, Olga; Burduniuc, Olga; Ceban, Emil; Gulea, AurelianThree new copper(II) complexes, [Cu(1,10-Phen)(L)] (1), [Cu(2,2’- Bpy)(L)] (2) and [Cu(3,4-Lut)(L)] (3), where H2L=2-[(2,4- dihydroxyphenyl)methylidene]-N-(prop-2-en-1-yl)hydrazine-1- carbothioamide, 1,10-Phen=1,10-phenanthroline, 2,2’-Bpy= 2,2’-bipyridine, 3,4-Lut=3,4-lutidine, have been synthesized and characterized by elemental analysis, FTIR spectroscopy and single crystal X-ray crystallography (1, 2). All compounds are mononuclear. The introduction of a monodentate N-heteroaromatic base (3,4-dimethylpyridine) has led to a significant increase of antimicrobial activity against Gram-negative Escherichia coli and antifungal activity against Candida albicans compared to the pro-ligand and the precursor complex [Cu- (L)H2O]. The introduction of bidentate N-heteroaromatic bases did not lead to such increase of antimicrobial and antifungal activities. Moreover, complex 3 surpasses the inhibitory activity of tetracycline toward Enterobacter cloacae and the inhibitory activity of fluconazole toward Candida parapsilosis and Cryptococcus neoformans. The study of antioxidant activity against cation radicals ABTS* + showed that complexes 1–3 are more active than Trolox, but only introduction of the monodentate Nheteroaromatic base (3,4-dimethylpyridine) led to the increase of antioxidant properties compared to the precursor complex.Item SINTEZA COMBINAȚIILOR COORDINATIVE ALE CUPRULUI(II) ȘI NICHELULUI(II) ÎN BAZA N(4)-(p-BENZOAT DE ETIL) TIOSEMICARBAZONELOR 5-Br (3,5-di Br) SALICILALDEHIDEI(CEP USM, 2021) Rusnac, AnnaThis article aims to synthesize 2 new organic substances N(4)-(p-ethyl-4-benzoate) thiosemicarbazone 5-Br (3,5-diBr) salicylaldehyde. Based on them, 15 coordination compounds of Cu (II) and Ni (II) were obtained. The organic compound was analysed by IR spectroscopy and characterized by 1H and 13C nuclear magnetic resonance (NMR). The coordination compounds were chemically characterized by elemental analysis and IR spectroscopy. On the basis of IR spectroscopy and elemental analysis showed that the ligands were coordinated to the metal tridentate ligands the sulfur-thionic atom, the azomethine nitrogen atom and the oxygen-phenolic atom. After recrystallization {Ni(HL1)NO3}·2H2O in a 1:3 binary solvent mixtures of N,N-dimethylformamide, ethanol. Single crystals have been obtained, and established the structure by X-ray analysis. Where the ligand is double deprotonated, due to the DMF which possesses basic properties and has favored its double deprotonation, coordinates to the central atom through the sulf-thionic atoms, azomethine nitrogen, oxygen-phenolic, the fourth position is occupied by oxygen from the DMF solvent molecule. The compound formed has a plane square geometry, in the outer sphere coordination compound: is a DMF, co-crystallization molecule.Item SYNTHESIS AND BIOLOGICAL ACTIVITY OF COPPER(II) COORDINATION COMPO UNDS WITH 2 - HYDROXY - 1 - NAPHTHALDEHYDE N (4) - ALLYL - 3 - THIOSEMICARBAZONE(CEP USM, 2020) Ulchina, Ianina; Tsapcov, Victor; Graur, Vasilii; Gulea, AurelianThe paper presents the synthesis of the 2-hydroxy-1-naphthaldehyde N(4)-allyl-3-thiosemicarbazone (H2L) and seven coordinationcompounds of copper with this ligand and heteroaromatic amines. The new obtained compounds were investigated by elemental analysis, IR spectroscopy and molar electric conductibility. For the ynthesized compounds the antibacterial and antifungal activities in vitro were studied on a series of standard strains, such as Staphylococcus aureus (ATCC 25923),Bacillus cereus (ATCC 11778),Bacillus subtilis (ATCC 6633), Candida albicans (ATCC 10231) andCandida krusei (ATCC 6258). The nature of heteroaromatic amines influences the activity of the oordination compounds that decreases in the following way: 3,4-Lut > 1,10-Phen > 2,2’-Bpy > Py > 4-Pic > 3 -Pic. Almost all stuied substancesmanifest high antioxidant activity towards ABT S•+that exceeds the activity of Trolox which is used as standard antioxidant.Item ANTIBACTERIAL, ANTIFUNGAL AND IN VITRO ANTILEUKAEMIA ACTIVITY OF METAL COMPLEXES WITH THIOSEMICARBAZONES(Wiley, 2015) Pahonțu, Elena; Julea, Felicia; Rosu, Tudor; Purcarea, Victor; Chumakov, Yurie; Petrenco, Petru; Gulea, Aurelian1-phenyl-3-methyl-4-benzoyl-5-pyrazolone 4-ethyl-thiosemicarbazone (HL) and its copper(II), vanadium(V) and nickel(II) complexes: [Cu(L)(Cl)]·C2H5OH·(1), [Cu(L)2]·H2O (2), [Cu(L)(Br)]·H2O·CH3OH (3), [Cu(L)(NO3)]·2C2H5OH (4), [VO2(L)]·2H2O (5), [Ni(L)2]·H2O (6), were synthesized and characterized. The ligand has been characterized by elemental analyses, IR, 1H NMR and 13C NMR spectroscopy. The tridentate nature of the ligand is evident from the IR spectra. The copper(II), vanadium(V) and nickel(II) complexes have been characterized by different physico-chemical techniques such as molar conductivity, magnetic susceptibility measurements and electronic, infrared and electron paramagnetic resonance spectral studies. The structures of the ligand and its copper(II) (2, 4), and vanadium(V) (5) complexes have been determined by single-crystal X-ray diffraction. The composition of the coordination polyhedron of the central atom in 2, 4 and 5 is different. The tetrahedral coordination geometry of Cu was found in complex 2 while in complex 4, it is square planar, in complex 5 the coordination polyhedron of the central ion is distorted square pyramid. The in vitro antibacterial activity of the complexes against Escherichia coli, Salmonella abony, Staphylococcus aureus, Bacillus cereus and the antifungal activity against Candida albicans strains was higher for the metal complexes than for free ligand. The effect of the free ligand and its metal complexes on the proliferation of HL-60 cells was tested.Item SYNTHESIS AND BIOLOGICAL ACTIVITY OF NICKEL AND COPPER COORDINATION COMPOUNDS OF 5-NITROFURAN-2-CARBALDEHYDE N(4)-ALLYL-3-THIOSEMICARBAZONE(CEP USM, 2014) Graur, Vasilii; Zariciuc, Elena; Tsapkov, Victor; Barba, Nina; Gulea, AurelianThe paper presents the synthesis of the ligand 5-nitrofuran-2-carbaldehyde N(4)-allyl-3-thiosemicarbazone (HL) and eight coordination compounds of copper(II) and nickel(II) with this ligand. The structure of thiosemicarbazone HL was studied using 1 H and 13С NMR spectroscopy. For the synthesized compounds their antimicrobial and antifungal activity was studied on a series of standard strains. For HL and Cu(HL)2(NO3)2 the antitumor activity towards human leukemia HL-60 cells was estimated. It was established that coordination compounds manifest better activity than free ligand.