Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Yakan, Hasan

doi:10.3906/kim-2002-76

Cited by 24 publications

(19 citation statements)

References 33 publications

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“…The frequency data of all of the molecules were consistent with those reported for similar compounds. [1,18,19]…”

Section: Vibrational Frequenciesmentioning

confidence: 99%

“…They have shown a wide spectrum of biological and medicinal properties such as antibacterial, [ 11 ] antiviral, [ 12 ] antimicrobial, [ 13 ] anticancer, [ 14 ] antituberculosis, [ 15 ] anticonvulsant, [ 16 ] urease inhibitory activity, [ 17 ] and antioxidant agents. [ 18–20 ] Recently, it has been revealed that thiosemicarbazones containing glyoxalic acid and isatin 2‐indolinones exhibit good inhibition against carbonic anhydrases (CAs). [ 21,22 ]…”

Section: Introductionmentioning

confidence: 99%

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Enzyme inhibition, molecular docking, and density functional theory studies of new thiosemicarbazones incorporating the 4‐hydroxy‐3,5‐dimethoxy benzaldehyde motif

Demir

Türkeş

Çavuş

et al. 2022

Archiv der Pharmazie

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New Schiff base-bearing thiosemicarbazones (1-13) were obtained from 4-hydroxy-3, 5-dimethoxy benzaldehyde and various isocyanates. The structures of the synthesized molecules were elucidated in detail. Density functional theory calculations were also performed to determine the spectroscopic properties of the compounds. Moreover, the enzyme inhibition activities of these compounds were investigated. They showed highly potent inhibition effects on acetylcholinesterase (AChE) and human carbonic anhydrases (hCAs) (K I values are in the range of 51.11 ± 6.01 to 278.10 ± 40.55 nM, 60.32 ± 9.78 to 300.00 ± 77.41 nM, and 64.21 ± 9.99 to 307.70 ± 61.35 nM for AChE, hCA I, and hCA II, respectively). In addition, molecular docking studies were performed, confirmed by binding affinities studies of the most potent derivatives.

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“…The frequency data of all of the molecules were consistent with those reported for similar compounds. [1,18,19]…”

Section: Vibrational Frequenciesmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Enzyme inhibition, molecular docking, and density functional theory studies of new thiosemicarbazones incorporating the 4‐hydroxy‐3,5‐dimethoxy benzaldehyde motif

Demir

Türkeş

Çavuş

et al. 2022

Archiv der Pharmazie

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“…Figure 2 shows some previously published thiosemicarbazide and thiosemicarbazone derivatives with anticancer and antimicrobial activities. Thiosemicarbazide and thiosemicarbazone derivatives are privileged moieties of profound interest in medicinal chemistry, as they possess different biological activities, such as anticancer (Bonaccorso et al, 2018), antimicrobial (Vekariya et al, 2017), antifungal (G. Yang et al, 2018), and antioxidant (Yakan, 2020) activities. Triapine VII and Dp44mT VIII are synthetic thiosemicarbazone analogs that have been reported to be potent anticancer agents (Finch et al, 2000; Krishan et al, 2016).…”

Section: Introductionmentioning

confidence: 99%

Coumarin derivatives with potential anticancer and antibacterial activity: Design, synthesis, VEGFR‐2 and DNA gyrase inhibition, and in silico studies

Emam

Hassan

Osman

et al. 2023

Drug Development Research

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A series of coumarin derivatives were designed, synthesized, and evaluated for their antiproliferative activity. Compound 3e exhibited significant antiproliferative activity and was further evaluated at five doses at the National Cancer Institute. It effectively inhibited vascular endothelial growth factor receptor-2 (VEGFR-2) with an IC 50 value of 0.082 ± 0.004 µM compared with sorafenib. While compound 3e significantly downregulated total VEGFR-2 and its phosphorylation, it markedly reduced the HUVEC's migratory potential, resulting in a significant disruption in wound healing. Furthermore, compound 3e caused a 22.51-fold increment in total apoptotic level in leukemia cell line HL-60(TB) and a 6.91-fold increase in the caspase-3 level. Compound 3e also caused cell cycle arrest, mostly at the G1/S phase. Antibacterial activity was evaluated against Gram-positive and Gram-negative bacterial strains. Compound 3b was the most active derivative, with the same minimum inhibitory concentration and minimum bactericidal concentration value of 128 μg/mL against K. pneumonia and high stability in mammalian plasma. Moreover, compounds 3b and 3f inhibited Gram-negative DNA gyrase with IC 50 = 0.73 ± 0.05 and 1.13 ± 0.07 µM, respectively, compared to novobiocin with an IC 50 value of 0.17 ± 0.02 µM. The binding affinity and pattern of derivative 3e toward the VEGFR-2 active site and compounds 3a-c and 3f in the DNA gyrase active site were evaluated using molecular modeling. Overall, ADME studies of the synthesized coumarin derivatives displayed promising pharmacokinetic properties.

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“…They are also used as versatile intermediates for synthesizing numerous compounds. They have shown a broad spectrum of chemical, biological and medicinal properties such as anti‐HIV, [11] antimicrobial [12] antiviral, [13] antibacterial, [14] anticonvulsant, [15] anticancer, [16] urease inhibitory activity, [17] antituberculosis, [18] cytotoxic activity, [19] and antioxidant agents [20–22] …”

Section: Introductionmentioning

confidence: 99%

Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors

Erdoğan,

Serdar Çavuş,

Muğlu

et al. 2023

Chemistry & Biodiversity

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Eleven new thiosemicarbazone derivatives (1‐11) were designed from nine different biologically and pharmacologically important isothiocyanate derivatives containing functional groups such as fluorine, chlorine, methoxy, methyl, and nitro at various positions of the phenyl ring, in addition to the benzyl unit in the molecular skeletal structure. First, their substituted‐thiosemicarbazide derivatives were synthesized from the treatment of isothiocyanate with hydrazine to synthesize the designed compounds. Through a one‐step easy synthesis and an eco‐friendly process, the designed compounds were synthesized with yields of up to 95% from the treatment of the thiosemicarbazides with aldehyde derivatives having methoxy and hydroxyl groups. The structures of the synthesized molecules were elucidated with elemental analysis and FT–IR, 1H NMR, and 13C NMR spectroscopic methods. The electronic and spectroscopic properties of the compounds were determined by the DFT calculations performed at the B3LYP/6‐311++G(2d,2p) level of theory, and the experimental findings were supported. They exhibited a highly potent inhibition effect on acetylcholinesterase (AChE) and carbonic anhydrases (hCAs) (KI values are in the range of 23.54±4.34 to 185.90±26.16 nM, 103.90±23.49 to 325.90 ±77.99 nM, and 86.15±18.58 to 287.70±43.09 nM for AChE, hCA I, and hCA II, respectively). Furthermore, molecular docking simulations were performed to explain each enzyme‐ligand complex's interaction.

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Preparation, structure elucidation, and antioxidant activity of new bis(thiosemicarbazone) derivatives

Cited by 24 publications

References 33 publications

Enzyme inhibition, molecular docking, and density functional theory studies of new thiosemicarbazones incorporating the 4‐hydroxy‐3,5‐dimethoxy benzaldehyde motif

Enzyme inhibition, molecular docking, and density functional theory studies of new thiosemicarbazones incorporating the 4‐hydroxy‐3,5‐dimethoxy benzaldehyde motif

Coumarin derivatives with potential anticancer and antibacterial activity: Design, synthesis, VEGFR‐2 and DNA gyrase inhibition, and in silico studies

Synthesis, Theoretical, in Silico and in Vitro Biological Evaluation Studies of New Thiosemicarbazones as Enzyme Inhibitors

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