Synthesis, photophysical and antioxidant properties of carbazole-based bis-thiosemicarbazones

Bingül, Murat; Şenkuytu, Elif; Sağlam, Mehmet F.; Boğa, Mehmet; Kandemir, Hakan; Sengul, İbrahim F.

doi:10.1007/s11164-019-03844-x

Cited by 28 publications

(23 citation statements)

References 40 publications

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“…The electronic spectral data of all of the compounds are summarized in Table 6. These values are in agreement with the results that were reported for similar compounds [11,[33][34][35].…”

Section: Uv-vis Interpretationssupporting

confidence: 93%

“…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%

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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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“…The electronic spectral data of all of the compounds are summarized in Table 6. These values are in agreement with the results that were reported for similar compounds [11,[33][34][35].…”

Section: Uv-vis Interpretationssupporting

confidence: 93%

Section: Introductionmentioning

confidence: 99%

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

Yakan¹

2020

Turk J Chem

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“…The acetyl-cholinesterase and butyrylcholinesterase inhibitory activities of the compounds 3 and 5 were tested by using a slightly modified Ellman method (47). Acetylthiocholine iodide (or butyrylthiocholine iodide) was used as substrate of the reaction and DTNB (5,5′dithiobis nitrobenzoic acid) was used for the measurement of the anticholinesterase activity.…”

Section: Anticholinesterase Activitymentioning

confidence: 99%

Evaluation of Acetyl- and Butyrylcholinesterase Enzyme Inhibitory Activities and Cytotoxic Activities of Anthraquinone Derivatives

OZKOK

Boğa

TUNEG

et al. 2022

Journal of the Turkish Chemical Society Section A: Chemistry

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In this study, the enzyme activity of anthraquinone compounds which were synthesized beforehand by our research group was investigated. Molecular docking studies were performed for compounds 1-(4-aminophenylthio)anthracene-9,10-dione (3) and 1-(4-chlorophenylthio)anthracene-9,10-dione (5). Compound 3 was synthesized from the reaction of 1-chloroanthraquinone (1) and 4aminothiophenol (2). Compound 5 was synthesized (1) from the reaction of 1-chloroanthraquinone (1) and 4-chlorothiophenol (4). Anthraquinone analogs (3, 5) were synthesized with a new reaction method made by our research group (2). Inhibitory effects of compounds 3 and 5 were investigated against acetylcholinesterase (AChE) and butyrylcholinesterase (BuChE) enzymes which are related to Alzheimer's Disease (AD). Compounds 3 and 5 exhibited strong anti-acetyl-and butyryl-cholinesterase inhibition activities than galanthamine used as standard compound (92.11±1.08 and 80.95±1.77 %, respectively). The EHOMO-ELUMO values, molecular descriptors, and the calculated UV-Vis spectra of anthraquinone derivatives were computed by B3LYP/6-31+G(d,p) levels in the CHCl3 phase. Based on the fluorescence property of the anthraquinone skeleton, the fluorescence activity of the bioactive anthraquinone analogue (5) was investigated. MTT test was performed to determine the cytotoxic effects of thioanthraquinone molecules 3 and 5. In MTT analyses, 3 compounds showed the highest effect against Ishikawa cells at a dose of 10 µg/mL, while compound 5 showed the highest effect at a dose of 50 µg/mL. The cell viability for compound 3 was 84.18% for 10 µg/mL and the cell viability for compound 5 was 75.02% for 50 µg/mL.

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“…The imine structure -N=CH-, commonly known as Schiff bases, is usually synthesized by removing water as a result of a condensation reaction between activated carbonyl groups such as aldehydes or ketones and primary amine [11][12][13]. Schiff bases and their derivatives are an important class of compounds in organic chemistry, medical and supramolecular chemistry [11][12][13][14]. Schiff base ligands can bind to metal ions through the presence of a free donor pair on the nitrogen atom to form metal complexes with potential biological activities [15][16].…”

mentioning

confidence: 99%

Synthesis of New Methoxy Actived Mono and Bis-indole Compounds

Kandemir

2022

Hittite Journal of Science and Engineering

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An indole hydrazone has successfully been synthesized employing Schiff base reaction conditions starting from 4,6-dimethoxy-2,3-diphenylindole-7-carbaldehyde with hydrazine hydrate. The reaction of this compound with acetone yielded indole based imine compound. The structure of targeted compound was identified by mass and 1H spectroscopy along with single crystal X-ray diffraction technique. Also, bromination of bis-indole with N-bromo succinimide was produced corresponding bromo bis-indol derivative.

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Synthesis, photophysical and antioxidant properties of carbazole-based bis-thiosemicarbazones

Cited by 28 publications

References 40 publications

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

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

Evaluation of Acetyl- and Butyrylcholinesterase Enzyme Inhibitory Activities and Cytotoxic Activities of Anthraquinone Derivatives

Synthesis of New Methoxy Actived Mono and Bis-indole Compounds

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