Facultatea de Chimie şi Tehnologie Chimică / Faculty of Chemistry and Chemical Technology
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Item 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(2020) Gulea, Aurelian; Graur, Vasilii; Diurici, E.; Ulchina, Ianina; Bouroș, Pavlina; Balan, Greta; Burduniuc, Olga; Țapcov, Victor; Rudic, Valeriu2-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.Item SYNTHESIS, STRUCTURE AND BIOLOGICAL ACTIVITY OF COORDINATION COMPOUNDS OF COPPER, NICKEL, COBALT, AND IRON WITH ETHYL N'-(2-HYDROXYBENZYLIDENE)-N-PROP-2-EN- 1-YLCARBAMOHYDRAZONOTHIOATE(2020) Gulea, Aurelian; Usataia, Irina; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter; Balan, Greta; Burduniuc, Olga; Țapcov, Victor; Rudic, ValeriuN-(Prop-2-en-1-yl)hydrazonocarbothioamide reacts with iodoethane in methanol with further addition of 2-hydroxybenzaldehyde to form hydroiodide of carbamohydrazonothioate (HL·HI). The coordination compounds were obtained by interaction of HL or HL·HI with copper, nickel, cobalt and iron salts CuLХ·nH2O [X = Cl–, Br–, NO3–; n = 0–1], Ni(L)2·HI·CH3OH, Сo(L)2X [X = I–, NO3–] and Fe(L)2NO3. The structures of three complexes were established by single crystal X-ray analysis. The synthesized complexes exhibit selective antimicrobial and antifungal activity against a series of standard microorganisms and fungi in the concentration range of 30–500 μg/mL. In addition, nickel and iron complexes selectively inhibit the growth and proliferation of cancer cells and do not adversely affect normal cells.Item SYNTHESIS, STRUCTURE, AND BIOLOGICAL ACTIVITY OF COORDINATION COMPOUNDS OF COBALT(II), NICKEL(II), AND COPPER(II) WITH N-(METHOXYPHENYL)-2-[(5-NITROFURYL)METHYLENE]HYDRAZINE CARBOTHIOAMIDES(2019) Gulea, Aurelian; Mitchevici, N.; Ciumacov, Iurie; Petrenko, Peter; Balan, Greta; Burduniuc, Olga; Țapcov, Victor4-(2-Methoxyphenyl)-, 4-(3-methoxyphenyl)-, and 4-(4-memoxyphenyl)-2-[(5-mttofuryl)methylene]-hydrazine carboxamide (HL1–3) react with hydrates of cobalt (nickel, copper) chloride (nitrate, acetate) with the formation of the M(HL1–3)2X2 (M = Co2+, Ni2+, Cu2+; X = Cl−, NO3−) and M(L1–3)2 (M = Ni2+, Cu2+) coordination compounds. Structure of the obtained compounds has been studied by means of X-ray diffraction analysis. Their antimicrobial and antifungal activity towards a series of Staphylococcus aureus, Escherichia coli, and yeast-like fungi standard strains has been investigated.Item SYNTHESIS, STRUCTURE, AND BIOLOGICAL ACTIVITY OF COPPER AND COBALT COORDINATION COMPOUNDS WITH SUBSTITUTED 2-(2-HYDROXYBENZYLIDENE)-N-(PROP-2-EN-1-YL)HYDRAZINE- CARBOTHIOAMIDES(2019) Gulea, Aurelian; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter A.; Balan, Greta; Burduniuc, Olga; Țapcov, Victor; Rudic, ValeriuThe reaction of N-(prop-2-en-1-yl)hydrazinecarbothioamide with substituted 2-hydroxybenzaldehydes afforded the corresponding Schiff bases which were used as ligands to obtain copper and cobalt coordination compounds Cu(NL1–6)X · n H2O (X = Cl−, NO3−; n = 0–3), Co(HL2)2NO3, and Co(NL6)2Cl. The structure of the isolated complexes was determined by NMR spectroscopy and X-ray analysis. The complexes were tested for antimicrobial and antifungal activity against S. aureus, E. coli, and yeast-like fungi. Inhibitory effect of the initial thioamides and their complexes against human myeloid leukemia HL-60 cancer cell line was also studied.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 NOVEL 2-FORMYLPYRIDINE 4-ALLYL-S- METHYLISOTHIOSEMICARBAZONE AND ZN(II), CU(II), NI(II) AND CO(III) COMPLEXES: SYNTHESIS, CHARACTERIZATION, CRYSTAL STRUCTURE, ANTIOXIDANT, ANTIMICROBIAL AND ANTIPROLIFERATIVE ACTIVITY(2019) Balan, Greta; Usataia, Irina; Graur, Vasilii; Ciumacov, Iurie; Petrenko, Peter; Gudumac, Valentin; Gulea, Aurelian; Pahonțu, Elena; Burduniuc, OlgaNew zinc (II), copper (II), nickel (II) and cobalt (III) complexes, [Zn (HL)2]I2 (1), [Cu (HL)Cl2] (2), [Cu (HL)Br2] (3), [Cu (HL)(H2O)2](ClO4)2 (4), [Ni (HL)2]I2·H2O (5), [Co(L)2]Cl (6), [Co(L)2]NO3 (7), [Co(L)2]I·[Co(L)2](I3) (8) were obtained with 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone (HL). The isothiosemicarbazone ligand was characterized by NMR (1H and 13C), IR spectroscopy and X-ray diffraction. All the complexes were characterized by elemental analysis, IR, UV–Vis, ESI-MS spectroscopy, molar conductivity, magnetic susceptibility measurements. X-ray diffraction analysis on the monocrystal and powder elucidated the structure of the complexes 1, 5, 7 and 8. The ligand and the complexes were tested for their antioxidant and antimicrobial activity against Staphylococcus aureus, Escherichia coli, Klebsiella pneumoniae and Candida albicans. Also, the antiproliferative properties of these compounds on human leukemia HL-60, human cervical epithelial HeLa, human epithelial pancreatic adenocarcinoma BxPC-3, human muscle rhabdomyosarcoma spindle, large multinucleated RD cells and normal MDCK cells have been investigated. The nickel complex 5 and cobalt complexes 6, 7 showed promising antiproliferative activity and low toxicity.Item INTRODUCING N-HETEROAROMATIC BASES INTO COPPER(II) THIOSEMICARBAZON COMPLEXES: A WAY TO CHANGE THEIR BIOLOGICAL ACTIVITY(2022) Ulchina, Ianina; Tsapkov, Victor I.; Graur, Vasilii O.; Chumakov, Yurii; 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 CU UNELE METALE 3D ÎN BAZA N(4)-(4-BENZOAT DE ETIL) TIOSEMICARBAZONE ALE DERIVAȚILOR ALDEHIDEI SALICILICE. PROPRIETĂȚI ANTIMICROBIENE, ANTIFUNGICE ȘI ANTIOXIDATIVE(CEP USM, 2021) Rusnac, Anna; Țurcanu, Nina; Burduniuc, Olga; Balan, Greta; Garbuz, Olga; Gulea, AurelianÎn lucrare este descrisă sinteza a 4 substanțe organice noi N(4)-(4-benzoat de etil) tiosemicarbazone ale derivaților aldehidei salicilice și a 29 combinații coordinative ale Cu(II), Ni(II), Zn(II) și Co(III). Structurile substanțelor sintetizate au fost confirmate cu ajutorul spectroscopiei IR și RMN, analizei elementale, magnetochimiei și, în cazul [Ni(L2) DMF]·DMF, difracției cu raze X. Studiul activității antimicrobiene s-a dovedit a fi în limita concentrației 0,125-0,500 mg/mL, iar activitate antifungică a înregistrat cel mai bun rezultat pe Cryptococcus neoformans la complexul {Ni(HL1)Cl}•C2H5OH•3H2O, unde CMI=0,016 mg/mL, fiind mai activ decât substanța martor Nistatina. Cele mai bune rezultate ale testului ABTS au fost înregistrate la ligandul H2L3(7) și la complexul {Ni(HL3) NO3}•H2O (7.8), care la concentrația 100 µM inhibă 54,4% din radicali ABTS•+.Item NOVEL 2-FORMYLPYRIDINE 4-ALLYL-S-METHYLISOTHIOSEMICARBAZONE AND ZN(II), CU(II), NI(II) AND CO(III) COMPLEXES: SYNTHESIS, CHARACTERIZATION, CRYSTAL STRUCTURE, ANTIOXIDANT, ANTIMICROBIAL AND ANTIPROLIFERATIVE ACTIVITY(John Wiley & Sons Ltd, 2020) Balan, Greta; Burduniuc, Olga; Usataia, Irina; Graur, Vasilii; Chumakov, Yurii; Petrenko, Peter; Gudumac, Valentin; Gulea, Aurelian; Pahontu, ElenaNew zinc (II), copper (II), nickel (II) and cobalt (III) complexes, [Zn (HL) 2 ]I 2 (1), [Cu (HL)Cl 2 ](2), [Cu (HL)Br 2 ](3), [Cu (HL)(H 2 O) 2 ](ClO 4 ) 2 (4), [Ni (HL) 2 ]I 2 H 2 O(5), [Co(L) 2 ]Cl (6), [Co(L) 2 ]NO 3 (7), [Co(L) 2 ]I[Co(L) 2 ](I 3 ) (8) were obtained with 2-formylpyridine 4-allyl-S-methylisothiosemicarbazone (HL). The isothiosemicarbazone ligand was characterized by NMR ( 1 H and 13 C), IR spectroscopy and X-ray diffraction. All the complexes were character- ized by elemental analysis, IR, UV–Vis, ESI-MS spectroscopy, molar conductiv- ity, magnetic susceptibility measurements. X-ray diffraction analysis on the monocrystal and powder elucidated the structure of the complexes 1,5, 7and 8. The ligand and the complexes were tested for their antioxidant and antimi- crobial activity against Staphylococcus aureus,Escherichia coli,Klebsiella pneumoniae and Candida albicans. Also, the antiproliferative properties of these compounds on human leukemia HL-60, human cervical epithelial HeLa, human epithelial pancreatic adenocarcinoma BxPC-3, human muscle rhabdomyosarcoma spindle, large multinucleated RD cells and normal MDCK cells have been investigated. The nickel complex 5and cobalt complexes 6,7showed promising antiproliferative activity and low toxicityItem SINTEZA ȘI PROPRIETĂȚILE ANTIBACTERIENE ȘI ANTIFUNGICE AL E COMPUȘILOR COORDINATIVI AI Fe (III) CU 4 - CICLOHEXILTIOSEMICARBAZONA 4 - BENZOIL - 3 - METIL - 1 - FENIL - 2 - PIRAZOLIN - 5 - ONĂ(CEP USM, 2020) Rusnac, Roman; Bîrca, Maria; Cotovaia, Aliona; Balan, Greta; Burduniuc, Olga; Gulea, Aurelian; Șova, SergiuÎn lucrare este relatată metoda de sinteză a trei combinații coordinative noi ale Fe (III) cu ciclohexiltiosemicarbazona 4 - benzoil - 3 - metil - 1 - fen il - 2 - pirazolin - 5 - onă. Activitatea antimicrobiană a compușilor studiați este moderată. Compusul coordi nativ [Fe(HL) 2 ]NO 3 ·H 2 O a demonstrat cea mai bună activitate față de tulpina de fungi Cryptococcus neoformans. Prin urmare, activitatea acestui compus este de 36 de ori mai bună comparativ cu nistatina; de 18 și 2 ori mai bună decât miconasolul și , respectiv , fluconazolul, preparte utilizate actualmente în profilaxia și tratamentul infecțiilor cauzate de aceste microorganisme .