Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

Detsi, Anastasia; Majdalani, Maya; Kontogiorgis, Christos; Hadjipavlou‐Litina, Dimitra; Kefalas, Panagiotis

doi:10.1016/j.bmc.2009.10.002

Cited by 260 publications

(181 citation statements)

References 75 publications

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“…Culture plastic dishes and plates (96-well) were purchased from Becton Dickinson (Franklin Lakes, NJ, USA). [7], (2Z)-6-methoxy-2-(phenylmethylene)-3(2H)-benzofuranone [8], (2Z)-6-methoxy-2-[(4-methoxyphenyl)methylene]-3(2H)-benzofuranone [9], (2Z)-2-[(3,4-dimethoxyphenyl)methylene]-6-methoxy-3(2H)-benzofuranone [10] and (2Z)-2-[(4-bromophenyl)methylene]-6-methoxy-3(2H)-benzofuranone [11] were synthesized by the oxidative cyclization of 2'-hydroxychalcone derivatives, according to previous methods (13). Also, (2Z)-2-[(3,4-dimethoxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone [12], (2Z)-2-[(4-fluorophenyl)methylene]-6-hydroxy-3(2H)-benzofuranone [13] [16] and (2Z)-2-[(3,4-dihydroxyphenyl)methylene]-6-hydroxy-3(2H)-benzofuranone [17] were synthesized by the condensation of 6-hydroxy-3(2H)-benzofuranone with selected benzaldehyde derivatives, according to previous methods (14).…”

Section: Methodsmentioning

confidence: 99%

Quantitative Structure–Cytotoxicity Relationship of Aurones

Sakagami

Masuda

Tomomura

et al. 2017

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Section: Methodsmentioning

confidence: 99%

Quantitative Structure–Cytotoxicity Relationship of Aurones

Sakagami

Masuda

Tomomura

et al. 2017

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“…Compound 1 was synthesized according to a published procedure. The synthesis of the free ligands precursor of dyes 2 [14] and 3 [15] was reported in literature.…”

Section: Synthesismentioning

confidence: 99%

Effect of Methoxy Substitution on Supramolecular Arrangement of Borondifluorides of 2'-Hydroxy Chalcones and their Solid-State NIR Fluorescence

D’Aléo¹,

Zaborova²,

Fagès³

2017

Croat. Chem. Acta

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This work describes the borondifluoride complexes of 2'-hydroxychalcone derivatives, 2 and 3, differently substituted with methoxy groups. Their optical study in dichloromethane reveals similar UV-vis absorption and fluorescence emission features in the visible spectral region that are close to those of the parent compound 1. While fluorescence quantum yields Φf are very low in solution, they are higher in the solid state, showing that aggregation-induced enhanced emission occurs. Remarkably, the solid-state emission spectra are strongly red-shifted reaching the near infrared (NIR) spectral range. Molecular structures of 2 and 3 were determined by single crystal X-ray diffraction. The data show the occurrence of tightly packed arrangements that favor strong π-π overlap between neighboring molecules. Such situation allows the generation of promising NIR emitting materials, such as compound 3 emitting at 784 nm with Φf = 0.07 that stands as one of the best NIR solidstate organic emitters.

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“…[3][4][5] Particularly in the pharmaceutical field, chalcone derivatives have found application on the treatment of different important diseases such as cancer, among others. [6][7][8][9][10] DNA is thought to be the main target of antitumoral drugs, and the binding between cisplatin complexes and DNA targets have been extensively studied. 11,12 Authors have shown that DNA interactions with several compounds affect the replication process and hence this inhibits the growth of the tumor cells, this means antitumor effects.…”

Section: Introductionmentioning

confidence: 99%

Interaction of Chalcones With Ct-Dna by Spectrophotometric Analysis and Theoreticalsimulations

et al. 2016

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publicado na web em 08/07/2016 Chalcones are open chain molecules precursors of flavonoids and isoflavonoids, found spread in edible plants. Because they are easily accessible trough Claisen Shmidt condensation, a great variety of derivatives are available. They have also shown potential in pharmacological and biological applications. It is known that chalcone derivatives display a role in the treatment of complex diseases such as cancer, among others, where the DNA is considered as the target for the action of these kinds of compounds. This action is commonly explained as the inhibition of the DNA replications and transcriptions through interactions. However, not conclusive associations between these DNA-Drug interactions and toxicity have been found. This research focuses on the capacity of a chalcone`s family to interact with DNA. Therefore, the binding constants for each compounds with Calf Thymus DNA [CT-DNA] were determined by spectrophotometric titration at room temperature. In addition, the effect of increasing the chalcone`s concentration over the relative viscosity of CT-DNA at room temperature was assessed. On the other hand, with the aim to find the optimal DNAchalcone configurations, as well as consistently predict their binding, a computational work was undertaken. To accomplish these goals within a reasonable time framework, an empirical scoring function (AScore) and a docking engine (ShapeDock) were performed using the ArgusLab package. The results of viscosity and docking measurement provided structural insights which suggest that chalcones bind with DNA via interaction as well as intercalation. The presence of interactions is also evidenced by the spectrophotometric study which showed luminescence quenching of the chalcones upon interaction with CT-DNA.

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Natural and synthetic 2′-hydroxy-chalcones and aurones: Synthesis, characterization and evaluation of the antioxidant and soybean lipoxygenase inhibitory activity

Cited by 260 publications

References 75 publications

Quantitative Structure–Cytotoxicity Relationship of Aurones

Quantitative Structure–Cytotoxicity Relationship of Aurones

Effect of Methoxy Substitution on Supramolecular Arrangement of Borondifluorides of 2'-Hydroxy Chalcones and their Solid-State NIR Fluorescence

Interaction of Chalcones With Ct-Dna by Spectrophotometric Analysis and Theoreticalsimulations

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