Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde

Muğlu, Halit; Yakan, Hasan; Bakır, Temelkan

doi:10.3906/kim-1910-13

Cited by 27 publications

(20 citation statements)

References 32 publications

(50 reference statements)

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“…The IR peaks of the compounds are presented in Table 3 (see Supplementary information). The frequency data of all of the molecules were consistent with those reported for similar compounds [8,10,28,29].…”

Section: Vibrational Frequenciessupporting

confidence: 88%

“…Antioxidant activity order was 4 (m -Cl) > 5 ( o-F) > 7 ( p -F) > 6 ( m-F). In similar studies, antioxidant activity among the halogen-containing compounds was -Cl > -F [8,43,44]. As for the effect of each position of the fluorine atom, o-F and p -F substituents have a strong inductive electron-attracting effect which causes easier hydrogen atom loss, whereas m -F substituent has poor inductive effect.…”

Section: Evaluation Of Antioxidant Activitymentioning

confidence: 83%

“…The electronic absorption spectra of the new bis(thiosemicarbazones) based on Schiff base derivatives (1)(2)(3)(4)(5)(6)(7)(8)(9)(10) show that in all obtained products absorption bands appeared in the range of 256-406 nm in dimethylsulfoxide (see Figures S28-S36 in compound 1 (258 nm). This transition is a characteristic benzenoid (B) band of the aromatic structure [32].…”

Section: Uv-vis Interpretationsmentioning

confidence: 97%

“…They are used as versatile intermediates for synthesizing numerous moieties as well. Thiosemicarbazones have shown numerous medicinal properties and biological activities such as anticonvulsant [1], antituberculosis [2], urease inhibitory [3], anticancer [4], antiviral [5], antimicrobial [1], antibacterial [6], and antioxidant activity [7][8][9][10][11].…”

Section: Introductionmentioning

confidence: 99%

“…In the compounds(1)(2)(3)(4)(5)(6)(7)(8)(9), the aromatic C signals of the aryl ring (C1-C6) were observed between 163 4. and 111.4 ppm and those from the terephthalaldehyde ring (C9-C10) were observed between 141.1 and 128.2 ppm.…”

mentioning

confidence: 99%

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

Yakan¹

2020

Turk J Chem

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Schiff-base-bearing new bis(thiosemicarbazone) derivatives were prepared from terephthalaldehyde and various thiosemicarbazides. FT-IR, 1 H NMR, 13 C NMR, and UV-Vis spectroscopic methods and elemental analysis were used to elucidate the identification of the synthesized molecules. The in vitro antioxidant activity of the synthesized compounds was analysed with the 1,1-diphenyl-2-picryl hydrazyl free-radical-trapping process. The synthesized compounds exhibited lower antioxidant activity than the standard ascorbic acid. IC 50 values of the synthesized molecules measured from 3.81 ± 0.01 to 29.05 ± 0.11 µ M. Among the synthesized compounds, compound 3 had the best antioxidant activity. Moreover, this study explained the structure-activity relationship of the synthesized molecules with different substituents in radical trapping reactions.

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Section: Vibrational Frequenciessupporting

confidence: 88%

Section: Evaluation Of Antioxidant Activitymentioning

confidence: 83%

Section: Uv-vis Interpretationsmentioning

confidence: 97%

Section: Introductionmentioning

confidence: 99%

mentioning

confidence: 99%

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

Yakan¹

2020

Turk J Chem

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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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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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Synthesis, spectroscopic studies, and antioxidant activities of novel thio/carbohydrazones and bis-isatin derivatives from terephthalaldehyde

Cited by 27 publications

References 32 publications

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

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

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

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

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