Redox-active metal complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part IV. Silver(I) complexes with hydrazone and thiosemicarbazone derivatives of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde

Loginova, N. V.; Ковальчук, Т. В.; Gres, A.T.; Osipovich, N. P.; Полозов, Г. И.; Halauko, Yu.S.; Faletrov, Yaroslav V.; Harbatsevich, H. I.; Hlushko, A.V.; Azarko, I.I.; Bokshits, Yu. V.

doi:10.1016/j.poly.2014.12.014

Cited by 17 publications

(6 citation statements)

References 34 publications

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“…We have chosen thiol-containing Schiff bases 1a – 1c as the ligands for improving the stability of the redox-active Ag(I) complexes in solution due to the high affinity of Ag(I) ions for the thiolate sulphur and the high stability of the Ag(I) complexes with organosulphur compounds ( K ~ 10 13 ) [ 46 ]. However, when evaluating the complexation effect of these ligands with Ag(I) ions on their antibacterial properties, one is forced to accept the fact that the newly synthesized Ag(I) complexes 2a – 2c are characterized by MIC values higher than those of the Ag(I) complexes 3a and 3b with sterically hindered phenolic derivatives previously reported by us [ 17 , 21 ] ( Table 3 ).…”

Section: Resultsmentioning

confidence: 99%

“…The aldehyde 1 was obtained by Duff reaction using 3,5-di- tert -butylbenzene-1,2-diol and hexamethylenetetramine in glacial acetic acid as starting materials [ 17 ]. Compounds 1b – 1c were prepared by the reaction of aromatic amines with 4,6-di- tert -butyl-2,3-dihydroxybenzaldehyde 1 in the molar ratio 1:1 using anhydrous methanol as a solvent.…”

Section: Methodsmentioning

confidence: 99%

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Silver(I) complexes with phenolic Schiff bases: Synthesis, anti-bacterial evaluation and interaction with biomolecules

Loginova¹,

Gvozdev²,

Osipovich³

et al. 2022

ADMET DMPK

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Novel Ag(I) complexes (2a–2c) with phenolic Schiff bases were synthesized using 4,6-di-tert-butyl-3-(((5-mercapto-1,3,4-thiadiazol-2-yl)imino)methyl)benzene-1,2-diol (1a), 4,6-di-tert-butyl-3-(((4-mercaptophenyl)imino)methyl)benzene-1,2-diol (1b), and 4,6-di-tert-butyl-3-(((3-mercaptophenyl)imino)methyl)benzene-1,2-diol (1c). They were examined by elemental analysis, FT-IR, UV-Vis, 1H-NMR spectroscopy, XRD, cyclic voltammetry, conductivity measurements, and biological methods. The complexes are characterized by distorted geometry of the coordination cores AgN2S2 (2c), AgNS (2b) and AgS2 (2a). These stable complexes were not typified by the intramolecular redox reaction in organic solvents resulting in the formation of silver nanoparticles (AgNPs). Antibacterial activity of 1a–1c and 2a–2c was evaluated in comparison with AgNPs and commonly used antibiotics. All the complexes were more active than the ligands against the bacteria tested (14), but they were less active than AgNPs and commonly used antibiotics. Both 1a–1c and their complexes 2a–2c exhibited the capability for the bovine heart Fe(III)-Cyt c reduction. The ligands 1b and 1c were characterized by the highest reduction rate among the compounds under study, and they showed a higher reducing ability (determined by cyclic voltammetry) as compared with that of their Ag(I) complexes 2b and 2c.

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Section: Resultsmentioning

confidence: 99%

Section: Methodsmentioning

confidence: 99%

Silver(I) complexes with phenolic Schiff bases: Synthesis, anti-bacterial evaluation and interaction with biomolecules

Loginova¹,

Gvozdev²,

Osipovich³

et al. 2022

ADMET DMPK

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“…Meanwhile, the presence of a methoxy group at the -meta position in P6 caused a higher SI value of 0.393 than that of P3. Based on the results of previous studies, the insertion of methyl [28] and hydroxyl [29][30] groups into the compounds enhanced the antiplasmodial activity. Nonetheless, it remained uncertain for the role of each functional group in improving the selectivity of the silver complexes.…”

Section: Antiplasmodial Studymentioning

confidence: 95%

Synthesis, Antiproliferative and Antimalarial Activities of Dinuclear Silver(I) Complexes with Triphenylphosphine and Thiosemicarbazones Ligands

et al. 2021

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A series of six sulfur-bridged dinuclear silver(I) thiosemicarbazone complexes were synthesized through the reaction of silver(I) nitrate with 4-phenyl-3-thiosemicarbazone derivatives together with triphenylphosphine (PPh3) (in a 1:1:2 molar ratio). Following structural characterizations using various techniques such as elemental analysis, Fourier-transform infrared (FTIR) spectroscopy, as well as 1H, 13C, 31P{1H}s, COSY, and 1H-13C nuclear magnetic resonance (NMR) spectroscopy, it was found that the thiosemicarbazone ligand exists in the form of a thione rather than thiol tautomer. Subsequently, MDA-MB-231 and MCF-7 breast cancer cell lines, as well as the HT-29 colon cancer cell lines, were used to investigate the in vitro antiproliferative activities of these complexes. In all cases, the IC50 values were in the potent micromolar range. Besides, the aforementioned complexes also had good antiplasmodial activity against chloroquine-resistant P. falciparum, as per the results of histidine-rich protein 2 (HRP2) assays and cytotoxicity evaluations of MDBK cells.

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“…Acylhydrazones 2a,b, 25 2c, 26 6, 27 4c, 28 and 9 (see Ref. 28) were synthesized by procedures described previously.…”

Section: Methodsmentioning

confidence: 99%

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

et al. 2021

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N-Benzylation of acylhydrazones of the hydroxybenzaldehyde series with 3,5-di-tert-butyl-4-hydroxybenzyl acetate was performed at room temperature in the absence of acid or base catalysts. Carboxamides do not react with 3,5-di-tert-butyl-4-hydroxybenzyl acetate under similar conditions. N-Benzylation of isoniazid and (diphenylphosphoryl)acetic acid hydrazones was shown to be an effi cient method for the synthesis of new hybrid compounds containing moieties of biologically active acylhydrazones and sterically hindered phenols. N-Benzyl derivatives of isoniazid and (diphenylphosphoryl)acetic acid hydrazones containing a hydroxy group at the ortho position of the aromatic ring are formed as individual E isomers with respect to the C=N double bond.

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Redox-active metal complexes of sterically hindered phenolic ligands: Antibacterial activity and reduction of cytochrome c. Part IV. Silver(I) complexes with hydrazone and thiosemicarbazone derivatives of 4,6-di-tert-butyl-2,3-dihydroxybenzaldehyde

Cited by 17 publications

References 34 publications

Silver(I) complexes with phenolic Schiff bases: Synthesis, anti-bacterial evaluation and interaction with biomolecules

Silver(I) complexes with phenolic Schiff bases: Synthesis, anti-bacterial evaluation and interaction with biomolecules

Synthesis, Antiproliferative and Antimalarial Activities of Dinuclear Silver(I) Complexes with Triphenylphosphine and Thiosemicarbazones Ligands

Synthesis of hybrid compounds by benzylation of acylhydrazones with 3,5-di-tert-butyl-4-hydroxybenzyl acetate

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