Synthesis, characterization and cytotoxicity of a new palladium(II) complex with a coumarin-derived ligand 3-(1-(3-hydroxypropylamino)ethylidene)chroman-2,4-dione. Crystal structure of the 3-(1-(3-hydroxypropylamino)ethylidene)-chroman-2,4-dione

Avdović, Edina H.; Stojković, Danijela Lj.; Jevtić, Verica V.; Kosic, Milica; Ristić, Biljana; Harhaji-Trajković, Ljubica; Vukić, Milena; Vuković, Nenad; Marković, Zoran; Potočňák, Ivan; Trifunović, Srećko R.

doi:10.1016/j.ica.2017.06.015

Cited by 24 publications

(13 citation statements)

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“…The elongation of C4=O3 (1.248(2) Å) bond, which is markedly longer than C2=O2 (1.223(2) Å) bond not involved in a strong hydrogen bond, and shortening of C1′−N1 (1.309(2) Å) bond in 3 can also be observed. Very similar bond lengths were observed in related compounds, like 3-(1-((o-toluidine)amino)ethylidene)-chroman-2,4-dione [72], 3-(1-(phenylamino)ethylidene)-chroman-2,4-dione [24], 3-(1-(3-hydroxypropylamino)propylidene)chroman-2,4-dione [73], 2-(1-(2,4-dioxochroman-3-ylidene)ethylamino)-3-methylbutanoate [74], 3-[(1-benzylamino)ethylidene]-2 H -chromene-2,4(3 H )-dione [75], or 3-[1-((2-hydroxyphenyl)amino)ethylidene]-2 H -chromene-2,4(3 H )-dione compound [76]. All other bond lengths and angles (Table S1) in the molecule of 3 are within normal ranges [77].…”

Section: Resultsmentioning

confidence: 58%

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

Dimić

Marković

Saso

et al. 2019

Oxidative Medicine and Cellular Longevity

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The newly synthesized coumarin derivative with dopamine, 3-(1-((3,4-dihydroxyphenethyl)amino)ethylidene)-chroman-2,4-dione, was completely structurally characterized by X-ray crystallography. It was shown that several types of hydrogen bonds are present, which additionally stabilize the structure. The compound was tested in vitro against different cell lines, healthy human keratinocyte HaCaT, cervical squamous cell carcinoma SiHa, breast carcinoma MCF7, and hepatocellular carcinoma HepG2. Compared to control, the new derivate showed a stronger effect on both healthy and carcinoma cell lines, with the most prominent effect on the breast carcinoma MCF7 cell line. The molecular docking study, obtained for ten different conformations of the new compound, showed its inhibitory nature against CDKS protein. Lower inhibition constant, relative to one of 4-OH-coumarine, proved stronger and more numerous interactions with CDKS protein. These interactions were carefully examined for both parent molecule and derivative and explained from a structural point of view.

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Section: Resultsmentioning

confidence: 58%

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

Dimić

Marković

Saso

et al. 2019

Oxidative Medicine and Cellular Longevity

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“…For the estimation of the chemical shifts, the GIAO method was used. This method has been shown to give good results for similar chemical compounds [ 25 , 26 ]. Theoretical chemical shifts, in DMSO and CDCl 3 as solvents, were calculated relative to TMS.…”

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%

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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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“…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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Synthesis, characterization and cytotoxicity of a new palladium(II) complex with a coumarin-derived ligand 3-(1-(3-hydroxypropylamino)ethylidene)chroman-2,4-dione. Crystal structure of the 3-(1-(3-hydroxypropylamino)ethylidene)-chroman-2,4-dione

Cited by 24 publications

References 20 publications

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

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

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

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