Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent

Dimić, Dušan; Marković, Zoran; Saso, Luciano; Avdović, Edina H.; Đorović, Jelena; Petrović, Isidora; Stanisavljevic, D.; Stevanović, Milena; Potočňák, Ivan; Samoľová, Erika; Trifunović, Srećko R.; Marković, Jasmina M. Dimitrić

doi:10.1155/2019/2069250

Cited by 19 publications

(22 citation statements)

References 78 publications

(69 reference statements)

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“…In the next step, the reaction of synthesized AHC with meta -hydroxyaniline and para -hydroxyaniline in dry methanol resulted in the formation of the final products L1 and L2 with good yields (89% and 86%). The coupling reaction was performed following the previously published synthesis of AHC [ 24 – 27 ]. To obtain compounds with very high purity, the final compounds were further purified by recrystallization from ethanol.…”

Section: Methodsmentioning

confidence: 99%

“…This paper presents the continuation of our work on the design of novel coumarin-based ligands and their corresponding palladium(II) complexes [24][25][26][27]. The compounds are tested for their antioxidative, in vitro, and in vivo cytotoxic effects and the effect on the activity of antioxidative enzymes.…”

Section: Introductionmentioning

confidence: 99%

“…Oxidative Medicine and Cellular Longevity with good yields (89% and 86%). The coupling reaction was performed following the previously published synthesis of AHC [24][25][26][27]. To obtain compounds with very high purity, the final compounds were further purified by recrystallization from ethanol.…”

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confidence: 99%

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Synthesis and Biological Screening of New 4-Hydroxycoumarin Derivatives and Their Palladium(II) Complexes

Avdović

Petrović

Stevanović

et al. 2021

Oxidative Medicine and Cellular Longevity

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Two newly synthesized 4-hydroxycoumarin bidentate ligands (L1 and L2) and their palladium(II) complexes (C1 and C2) were screened for their biological activities, in vitro and in vivo. Structures of new compounds were established based on elemental analysis, 1H NMR, 13C NMR, and IR spectroscopic techniques. The obtained compounds were tested for their antioxidative and cytotoxic activities and results pointed to selective antiradical activity of palladium(II) complexes towards •OH and -•OOH radicals and anti-ABTS (2,2 ′ -Azino-bis(3-ethylbenzothiazoline-6-sulfonic acid) cation radical) activity comparable to that of ascorbate. Results indicated the effect of C1 and C2 on the enzymatic activity of the antioxidative defense system. In vitro cytotoxicity assay performed on different carcinoma cell lines (HCT166, A375, and MIA PaCa-2), and one healthy fibroblast cell line (MRC-5) showed a cytotoxic effect of both C1 and C2, expressed as a decrease in carcinoma cells’ viability, mostly by induction of apoptosis. In vivo toxicity tests performed on zebrafish embryos indicated different effects of C1 and C2, ranging from adverse developmental effect to no toxicity, depending on tested concentration. According to docking studies, both complexes (C1 and C2) showed better inhibitory activity in comparison to other palladium(II) complexes.

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Section: Methodsmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis and Biological Screening of New 4-Hydroxycoumarin Derivatives and Their Palladium(II) Complexes

Avdović

Petrović

Stevanović

et al. 2021

Oxidative Medicine and Cellular Longevity

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“…HPLC data and chromatograms can be found in Supplementary Material, Tables S1-S5 and Figures S11-S15, respectively. The 2,4-dione tautomeric form of these derivatives was assumed on the basis of the obtained spectroscopy data and X-ray structure which was determined for a similar type of compounds in our previous studies [35][36][37].…”

Section: Synthesismentioning

confidence: 99%

Green One-Pot Synthesis of Coumarin-Hydroxybenzohydrazide Hybrids and Their Antioxidant Potency

et al. 2021

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Compounds from the plant world that possess antioxidant abilities are of special importance for the food and pharmaceutical industry. Coumarins are a large, widely distributed group of natural compounds, usually found in plants, often with good antioxidant capacity. The coumarin-hydroxybenzohydrazide derivatives were synthesized using a green, one-pot protocol. This procedure includes the use of an environmentally benign mixture (vinegar and ethanol) as a catalyst and solvent, as well as very easy isolation of the desired products. The obtained compounds were structurally characterized by IR and NMR spectroscopy. The purity of all compounds was determined by HPLC and by elemental microanalysis. In addition, these compounds were evaluated for their in vitro antioxidant activity. Mechanisms of antioxidative activity were theoretically investigated by the density functional theory approach and the calculated values of various thermodynamic parameters, such as bond dissociation enthalpy, proton affinity, frontier molecular orbitals, and ionization potential. In silico calculations indicated that hydrogen atom transfer and sequential proton loss–electron transfer reaction mechanisms are probable, in non-polar and polar solvents respectively. Additionally, it was found that the single-electron transfer followed by proton transfer was not an operative mechanism in either solvent. The conducted tests indicate the excellent antioxidant activity, as well as the low potential toxicity, of the investigated compounds, which makes them good candidates for potential use in food chemistry.

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“…The coumarin (benzo-α-pyrone) skeleton, a common but important pharmacophore, can interact noncovalently with various active sites, which brings about the various biological activities of coumarins and their derivatives. Therefore, benzopyrone has been widely used as a structural subunit for the discovery of anti-cancer agents [29,30,31,32].…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis and Preliminary Biological Evaluation of Benzylsulfone Coumarin Derivatives as Anti-Cancer Agents

et al. 2019

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In this work, a series of benzylsulfone coumarin derivatives 5a–5o were synthesized and characterized. Kinase inhibitory activity assay indicated that most of the compounds showed considerable activity against PI3K. Anti-tumor activity studies of the active compounds were also carried out in vitro on the Hela, HepG2, H1299, HCT-116, and MCF-7 tumor cell lines by MTS assay. The structure–activity relationships (SARs) of these compounds were analyzed in detail. Compound 5h exhibited the most potent activities against the mentioned cell lines with IC50 values ranging from 18.12 to 32.60 μM, followed by 5m with IC50 values of 29.30–42.14 μM. Furthermore, 5h and 5m clearly retarded the migration of Hela cells in vitro. Next, an in silico molecular docking study was conducted to evaluate the binding models of 5h and 5m towards PI3Kα and PI3Kβ. Collectively, the above findings suggested that compounds 5h and 5m might be promising PI3K inhibitors deserving further investigation for cancer treatment.

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Synthesis and Characterization of 3-(1-((3,4-Dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione as a Potential Antitumor Agent

Cited by 19 publications

References 78 publications

Synthesis and Biological Screening of New 4-Hydroxycoumarin Derivatives and Their Palladium(II) Complexes

Synthesis and Biological Screening of New 4-Hydroxycoumarin Derivatives and Their Palladium(II) Complexes

Green One-Pot Synthesis of Coumarin-Hydroxybenzohydrazide Hybrids and Their Antioxidant Potency

Design, Synthesis and Preliminary Biological Evaluation of Benzylsulfone Coumarin Derivatives as Anti-Cancer Agents

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