872131-45-8Relevant articles and documents
Design, synthesis and QSAR study of 2′-hydroxy-4′-alkoxy chalcone derivatives that exert cytotoxic activity by the mitochondrial apoptotic pathway
Marquina, Silvia,Maldonado-Santiago, Maritza,Sánchez-Carranza, Jessica Nayelli,Antúnez-Mojica, Mayra,González-Maya, Leticia,Razo-Hernández, Rodrigo Said,Alvarez, Laura
, p. 43 - 54 (2018/11/27)
Eleven 4′-alkoxy chalcones were synthesized and biologically evaluated for their antiproliferative activity against four human tumor cell lines (PC-3, MCF-7, HF-6, and CaSki). Compounds 3a-3d and 3f were selective against PC-3, with IC50 values ranging from 8.08 to 13.75 μM. In addition, chalcones 3a-3c did not affect the normal fibroblasts BJ cells. The most active and selective compounds were further evaluated for their effect on the progression of cell cycle in PC-3 cells, and chalcones 3a and 3c induced a G2/M phase arrest. Furthermore, it was found that these three chalcones induced the mitochondrial apoptotic pathway by regulating Bax and Bcl-2 transcripts and by increasing caspase 3/7 activation. Otherwise, the QSAR model indicates that the double bond of the α,β-unsaturated carbonyl, as well as the planar structure geometry, are important to the biological activity of the synthetized chalcones. Based on these studies, it was concluded that withdrawing substituents in ring A, decrease the antiproliferative activity. This is related to the possible mechanism of action of these compounds, where a Michael addition needs to take place in order to be a potent anticancer agent.
Origin of Spectral Features and Acid-Base Properties of 3,7-Dihydroxyflavone and Its Monofunctional Derivatives in the Ground and Excited States
Serdiuk, Illia E.,Roshal, Alexander D.,B?azejowski, Jerzy
, p. 4325 - 4337 (2016/07/11)
Comprehensive spectral investigations of 3,7-dihydroxyflavone and its two derivatives, which each contain a methyl-blocked hydroxyl group, reveal complex radiation absorption in the 300-450 nm range and emission in the 370-650 nm range. The absorption and fluorescence characteristics of these compounds depend on the pH/H0 of the water/methanol media, which is caused by the existence of the compounds in various protolytic (cationic, neutral, anionic) and tautomeric forms. Combined analysis of steady-state, time-dependent and fluorescence decay spectral data enabled the identification of the emitting species, determination of their lifetimes with respect to radiative and nonradiative deactivation processes, fluorescence quantum yields, protolytic and tautomeric abilities under various conditions, and acidic dissociation constants of the cationic, neutral, and anionic forms of the compounds. Results of calculations carried out at the DFT and TD DFT levels of theory generally confirmed the experimental findings concerning tautomeric/protolytic transformations and equilibria. Computational methods also provided insight into possible tautomerization pathways. Electronically excited molecules are generally much more susceptible to tautomerization and acidic dissociation than ground-state ones. 3,7-Dihydroxyflavone exhibits distinguishable features among the compounds investigated and can be considered as potential spectral indicator of properties (polarity, hydrophobicity, hydrogen-bonding ability) and acidity/basicity of liquid environments.
Single and double intramolecular proton transfers in the electronically excited state of flavone derivatives
Serdiuk,Roshal
, p. 102191 - 102203 (2015/12/11)
In an attempt to create a flavone derivative able to take part in Excited State Intramolecular Double Proton Transfer (ESIDPT), we synthesized two carbonyl derivatives of 3,7-dihydroxyflavone, both containing two different proton-transfer sites as well as related carbonyl derivatives of 3-hydroxyflavone and 7-hydroxyflavone. All the examined hydroxyflavones were found to participate in the Excited State Intramolecular Proton Transfer (ESIPT). ESIPT which involves 3-hydroxyl and 4-carbonyl groups was found to have a higher barrier compared to ESIPT involving 7-hydroxyl and 6/8-carbonyl fragments. According to the data presented, 3,7-dihydroxy-2-phenyl-6-(3-phenylpropanoyl)-4H-chromen-4-one undergoes a two-stage ESIDPT with formation of an intermediate tautomer. This kind of ESIDPT leads to a tautomeric form with an abnormally low rate of radiative deactivation of the excited state, which conditions low fluorescence quantum yield. The behavior of 3,7-dihydroxy-4-oxo-2-phenyl-4H-chromene-8-carbaldehyde in the electronically excited state is similar to 3-hydroxyflavone derivatives, thus we conclude the occurrence of a single ESIPT in this compound.
Quantum-chemical analysis of the Algar-Flynn-Oyamada reaction mechanism
Serdiuk,Roshal,B?a?ejowski
, p. 396 - 403 (2014/08/05)
This work is devoted to improving the understanding of Algar-Flynn-Oyamada reaction mechanism and the analysis of factors that affect the formation of flavonols. The calculation of thermodynamic parameters for the key reaction steps pointed to a mechanism involving chalcone epoxides as intermediates. A correlation was identified between the nucleophilicity of oxygen atom at position 2' of epoxide anions and the yields of flavonols. An increased charge at the nucleophilic center was shown to reduce the effectiveness of β-cyclization of epoxide anions.
Acidic rearrangement of (benzyloxy)chalcones: A short synthesis of chamanetin
Sagrera, Gabriel,Seoane, Gustavo
experimental part, p. 4190 - 4202 (2011/03/20)
Treatment of (benzyloxy)chalcones with trifluoroacetic acid in refluxing chloroform gave several new benzyl(hydroxy)flavanones in high yields and good regioselectivities. By using this procedure, we prepared the natural compound chamanetin in good yield from readily available reagents. Georg Thieme Verlag Stuttgart - New York.
Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure-activity relationships
Cabrera, Mauricio,Simoens, Macarena,Falchi, Gabriela,Lavaggi, M. Laura,Piro, Oscar E.,Castellano, Eduardo E.,Vidal, Anabel,Azqueta, Amaia,Monge, Antonio,de Cerain, Adela Lopez,Sagrera, Gabriel,Seoane, Gustavo,Cerecetto, Hugo,Gonzalez, Mercedes
, p. 3356 - 3367 (2008/02/07)
A series of synthetic chalcones, flavanones, and flavones has been synthesized and evaluated for antitumor activity against the human kidney carcinoma cells TK-10, human mammary adenocarcinoma cells MCF-7 (estrogen receptor-positive), and human colon adenocarcinoma cells HT-29. The most active series is the chalcone ones with the best results against TK-10 and HT-29 cells. Fourteen out of 53 analyzed compounds resulted very active against at least two of the studied tumoral cells. Alkaline single cell gel electrophoresis, comet assay, was performed as a study of the chromosomal aberrations promoted by the compounds on normal cells. Four active and two inactive chalcones were studied in the comet assay against normal human kidney cells (HK-2). A structure-activity relationship analysis of these compounds was performed and for 4- and 3,4-disubstituted derivatives a quantitative correlation was obtained in the case of anti-HT-29 activity.
Studies on the metabolism of propafenone. 1st comm.: Synthesis and chromatographic/mass spectrometric properties of the labelled compound and of the reference substances
Hege,Weymann,Lietz
, p. 843 - 849 (2007/10/02)
The synthesis of 14C-propafenone and 2H-propafenone (propafenone: 2-(2'-hydroxy-3'-propylamino-propoxy)-ω-phenyl-propiophenone hydrochloride) and some reference compounds is described. The thin-layer chromatographic, high-performance liquid and gas chromatographic properties of the substances are described. Propafenone and the reference substances were studied by mass spectrometry and compared with each other, with respect to structural elucidation of the metabolites. The chromatographic and mass spectrometric data (key ions) enables the metabolites of propafenone to be identified in biological material.
