Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment‐Independent 3D QSAR Models

Božić, Aleksandra; Bjelogrlić, Snežana K.; Novaković, Irena; Filipović, Nenad R.; Petrović, Predrag; Marinković, Aleksandar D.; Todorović, Tamara R.; Cvijetić, Ilija N.

doi:10.1002/slct.201702691

Cited by 16 publications

(6 citation statements)

References 26 publications

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“…In addition to the solvent effect, results of the correlations of the absorption maxima with Hansen's Fig. 9 ICT processes in E isomers of monothiocarbohydrazones (1)(2)(3)(4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15)(16)(17)(18). Left images, difference between densities in first excited and ground state (red and blue, density increase and decrease upon transition, respectively); right images, positions of barycenters for charge loss (cyan circle) and charge gain (violet circle) upon transition solubility parameters showed that the dispersion forces are the most dominant interactions between the examined mTCHs and the surrounding medium.…”

Section: Discussionmentioning

confidence: 99%

“…Depending on the molar ratio of the reactants (1:1 or 1:2), mono-or bis-substituted thiocarbohydrazones can be obtained [1,2]. Many of these compounds tested so far have shown exceptionally good antimicrobial [3][4][5], antioxidant [6,7], and antitumor [8,9] activity. Due to their structure, more specifically to the presence of nitrogen and sulfur atoms, they are easily coordinated and can build complexes with many transition metals [10,11].…”

Section: Introductionmentioning

confidence: 99%

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Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

et al. 2021

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Derivatives of thiocarbohydrazone studied so far have shown great biological activity such as antioxidant, antimicrobial, and anticancer. Most of these compounds are bis-substituted derivatives, while monothiocarbohydrazones are much less investigated. Еighteen monothiocarbohydrazones were synthesized and subjected to physicochemical characterization in order to facilitate the examination of their potential biological activity and application in future studies. The structure of synthesized derivatives was confirmed with NMR and FT-IR spectroscopy, and with elemental analysis. For one of the compounds, single-crystal X-ray diffraction analysis was performed. Specific and non-specific molecular interactions were interpreted by LSER principles, using Catalan's model. For additional information about the dominance and influence of the interactions presented, correlations with Hansen's solubility parameters were calculated. Influence of the type and position of the substituent on absorption maxima was determined with LFER (linear free-energy relationship) principles, using Hammett's equation. Acidity constants of the synthesized compounds were theoretically calculated and experimentally determined. Moreover, the excitation of a molecule by a photon of UV-Vis light was interpreted by time-dependent density functional theory (TD-DFT) calculations of UV absorption bands, and intramolecular charge transfer (ICT) was quantified by calculations of the charge transfer distances (D CT ).

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Section: Discussionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

et al. 2021

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“…Recently, Božic et al explored the antimicrobial activity of twenty-two mono-and bisthiocarbohydrazones derived from 2-acetylpyridine and related carbonyl compounds (9-11, Scheme 4) [54]. The antibacterial activity was evaluated using four different strains of Gram-positive bacteria (Bacillus subtilis, Staphylococcus aureus, Clostridium sporogenes and Kocuria rhizophila) and four different strains of Gram-negative bacteria (Escherichia coli, Pseudomonas aeruginosa, Proteus hauseri and Salmonella enterica subsp.…”

Section: Symmetric Thiocarbohydrazones Derived From Pyridyl and Relatmentioning

confidence: 99%

“…In a comparison with symmetric TCHs (see previous section), quinolyl and pyridyl mono TCHs (22-24, Scheme 8) were tested for both their antitumor [52] and antimicrobial activity [54]. In the former report, mono-TCHs treatments induced considerably higher pro-oxidative activity compared to their bis-structural analogues; the increased pro-oxidant capacity was probably related to the terminal hydrazide group.…”

Section: Asymmetric Thiocarbohydrazones Derived From Pyridyl and Relamentioning

confidence: 99%

Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review

2019

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Although organic compounds account for more than 99% of currently approved clinical drugs, the established clinical use of cisplatin in cancer or auranofin in rheumatoid arthritis have paved the way to several research initiatives to identify metal-based drugs for a wide range of human diseases. Nitrogen and sulfur donor ligands, characterized by different binding motifs, have been the subject in recent years of one of the main research areas in coordination chemistry. Among the nitrogen/sulfur compounds, very little is known about thiocarbohydrazones (TCH), the higher homologues of the well-known thiosemicarbazones (TSC), and their metal complexes. The extra hydrazine moiety provides the ligands of variable metal binding modes, structural diversity and promising biological implications. The interesting coordination chemistry of TCH has mainly been focused on symmetric derivatives, which are relatively simple to synthesize while few examples of asymmetric ligands have been reported. This informative review on TCHs and their metal complexes will be helpful for improving the design of metal-based pharmaceuticals for applications ranging from anticancer to antinfective therapy.

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“…Among their biological activities are antibacterial, anticancer, antifungal, anti-inflammatory, antimycobacterial, antioxidative, antituberculosis, and herbicidal activities. Furthermore, thiocarbohydrazones are utilized as starting materials in the synthesis of industrial and biological compounds with the potential of developing a new class of antileishmanial compounds [8][9][10]. The fungicidal activity of thiocarbohydrazones has been tested on textile fabrics [11], and recently, the synthesis and investigation of a series of 2-acetylpyridine thiocarbohydrazones as inactivators of Herpes simplex virus-1 (HSV-1) ribonucleotide reductase showed better results compared to analogous 2-acetylpyridine thiosemicarbazone derivatives [12].…”

Section: ■ Introductionmentioning

confidence: 99%

Synthesis, Thermal Analysis, and Thermodynamic Properties Study of New Quinoline Derivative and Their V(IV), Co(II), and Cu(II) Complexes

Aldoghachi

Alsalim

et al. 2022

Indones. J. Chem.

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A new ligand (E)-2-((2-chloro-6-methylquinoline-3-yl)methylene)-N'-((E)-(2-chloro-6-methylquinoline-3-yl)methylene)hydrazine-1-carbothiohydrazide (QH) was prepared by reacting hydrazine hydrate with carbon disulfide to yield thiocarbohydrazide. The thiocarbohydrazide in the second step was treated with a quinoline derivative 2-chloro-6-methylquinoline-3-carbaldehyde to yield the ligand. The ligand was identified by spectroscopic techniques FTIR, 1H-NMR, and 13C-NMR. Next, vanadium (V), cobalt (Co), and copper (Cu) complexes were prepared in the [M:L] ratio of 1:1 (QV, QCo, QCu). The complexes were characterized using FTIR, ESI, magnetic susceptibility, and molar conductivity. The thermal analysis (TGA) of V(IV), Co(II), and Cu(II) complexes were studied. The activation thermodynamic parameters, such as the energy of activation, enthalpy, entropy, and free energy change of the complexes, were evaluated, and the stabilities of the thermal decomposition of the complexes were discussed.

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Antimicrobial Activity of Thiocarbohydrazones: Experimental Studies and Alignment‐Independent 3D QSAR Models

Cited by 16 publications

References 26 publications

Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

Synthesis, physicochemical characterization, and TD–DFT calculations of monothiocarbohydrazone derivatives

Biological Applications of Thiocarbohydrazones and Their Metal Complexes: A Perspective Review

Synthesis, Thermal Analysis, and Thermodynamic Properties Study of New Quinoline Derivative and Their V(IV), Co(II), and Cu(II) Complexes

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