Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships

Cabrera, Mauricio; Simoens, Macarena; Falchi, Gabriela; Lavaggi, María Laura; Piro, Oscar E.; Castellano, Eduardo E.; Vidal, Anabel; Azqueta, Amaya; Monge, Antonio; Ceráin, Adela López de; Sagrera, Gabriel; Seoane, Gustavo; Cerecetto, Hugo; González, Mercedes

doi:10.1016/j.bmc.2007.03.031

Cited by 269 publications

(146 citation statements)

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“…Total twelve compounds (4)(5)(6)(7)(8)(9)(10)(11)(12)(13)(14)(15) were synthesized as shown Inhibitory Effects on LPS-induced ROS and NO Production in RAW 264.7 Macrophages. Inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages of prepared compounds is shown in Table 1.…”

Section: Resultsmentioning

confidence: 99%

“…Among compounds 8-11, which possess 3-thienyl-phenylpropenone as a basic skeleton without hydroxyl group on phenyl ring (8), and with a single hydroxyl group at ortho, meta or para position on phenyl ring (9, 10, 11, respectively), compound 11 displayed the most significant inhibitory activity of LPSinduced ROS and NO production in RAW 264.7 macrophages (2.2 and 0.70 µM of IC 50 , respectively), which also indicated that para-hydroxyphenyl moiety is important for inhibitory activities on both LPS-induced ROS and NO production. Among compounds 12-15, which possess 2-furanyl-phenylpropenone as a basic skeleton without hydroxyl group on phenyl ring (12), and with a single hydroxyl group at ortho, meta or para position on phenyl ring (13,14,15, respectively), unfortunately compound 15 which possess para-hydroxyphenyl moiety displayed cytotoxicity in RAW 264.7 macrophages on both LPS-induced ROS and NO production. From those results it was observed that thienyl/ furanyl-phenylpropenones which do not possess hydroxyl group on phenyl moiety did not exhibited significant inhibitory activity of LPS-induced ROS production in RAW 264.7 macrophages.…”

Section: Resultsmentioning

confidence: 99%

“…Numerous polyphenolic phytochemicals such as resveratrol, curcumin, flavonoids, epigallocatechin gallate, and chalcones have been well studied and reported to interfere with specific stages of the carcinogenic process. [24][25][26][27] In our previous results, we observed that introduction of hydroxyl group on phenyl moiety increased bioa These authors contributed equally to this work. …”

Section: -23mentioning

confidence: 96%

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Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study

Kadayat¹,

Kim²,

Nam³

et al. 2014

Bulletin of the Korean Chemical Society

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Twelve thienyl/furanyl-hydroxyphenylpropenones were systematically designed and synthesized, and evaluated for their inhibitory effect on LPS-induced ROS and NO production in RAW 264.7 macrophages. Compound 11 displayed the most significant inhibitory activity of LPS-induced ROS and NO production in RAW 264.7 macrophages. Structure-activity relationship study indicated that para-hydroxyphenyl moiety plays an important role for inhibitory activities on both LPS-induced ROS and NO production as well as 3-thienyl moiety on molecule.

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Section: Resultsmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Section: -23mentioning

confidence: 96%

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Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study

Kadayat¹,

Kim²,

Nam³

et al. 2014

Bulletin of the Korean Chemical Society

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“…Chalcones with hydroxyl groups seem to have more potent anti-proliferative properties than other chalcone derivatives, at least on cancer cells (Cabrera et al, 2007).…”

Section: Discussionmentioning

confidence: 97%

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

et al. 2015

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CitationIn vitro structure-toxicity relationship of chalcones in human hepatic stellate cells 2015 Toxicology This is a PDF file of an unedited manuscript that has been accepted for publication. As a service to our customers we are providing this early version of the manuscript. The manuscript will undergo copyediting, typesetting, and review of the resulting proof before it is published in its final form. Please note that during the production process errors may be discovered which could affect the content, and all legal disclaimers that apply to the journal pertain. In vitro AbstractXanthohumol (XN), the major prenylated chalcone from hops (Humulus lupulus L.), has received much attention within the last years, due to its multiple pharmacological activities including anti-proliferative, anti-inflammatory, antioxidant, pro-apoptotic, anti-bacterial and anti-adhesive effects. However, there exists a huge number of metabolites and structurallyrelated chalcones, which can be expected, or are already known, to exhibit various effects on cells. We have therefore analyzed the effects of XN and 18 other chalcones in a panel, consisting of multiple cell-based assays. Readouts of these assays addressed distinct aspects of cell-toxicity, like proliferation, mitochondrial health, cell cycle and other cellular features. Besides known active structural elements of chalcones, like the Michael system, we have identified several moieties that seem to have an impact on specific effects and toxicity in human liver cells in vitro. Based on these observations, we present a structure-toxicity model, which will be crucial to understand the molecular mechanisms of wanted effects and unwanted side-effects of chalcones.

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“…11 The growing interest in these compounds and their potential use in medicinal applications is indicated by the increasing number of publications concerning the synthesis and biological evaluation of chalcone analogues. [1][2][3][4][5][6][7][8][9][10][11] Their properties are related, among other factors, to its great conformational freedom as well as to the several patterns of substitution of A and B rings. 12 Thus, the correct structural determination and the knowledge about three-dimensional (3D) atomic structure of chalcones are crucial to understand their properties.…”

Section: Introductionmentioning

confidence: 99%

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

Costa

Gomes

Silva

et al. 2017

J. Braz. Chem. Soc.

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In this paper we investigated the ability of the GIAO-mPW1PW91/6-31G(d)//mPW1PW91/6-31G(d) level of theory to predict the 13 C nuclear magnetic resonance (NMR) chemical shifts of the 2'-hydroxy-3,4,5-trimethoxy-chalcone molecule. Two different approaches were used. First: the absolute shieldings σ for all carbon atoms in each geometrically optimized conformers of the 2'-hydroxy-3,4,5-trimethoxy-chalcone molecule were calculated at the GIAO-mPW1PW91/6-31G(d)// mPW1PW91/6-31G(d) level of theory. This approach is further used to generate weighted average values for each atom considering the previously obtained conformational distribution. Second: only the σ for the lowest energetic conformer will be taken to account. The robustness of the method was evaluated for two other chalcones: (E)-1-(4-hydroxy-3-methoxyphenyl)-3-(3,5-di-tert-butyl-4-hydroxyphenyl)prop-2-en-1-one and (E)-1-(4-aminophenyl)-3-(3,4-dimethoxyphenyl)prop-2-en-1-one, corroborating the ability of the method in chemical shift prevision. Although, both approaches were able to reproduce the chemical shifts of the 2'-hydroxy-3,4,5-trimethoxy-chalcone, significant differences in the calculated values for C-4 and methoxy carbons were observed. The best results were obtained using the second approach (II).

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Synthetic chalcones, flavanones, and flavones as antitumoral agents: Biological evaluation and structure–activity relationships

Cited by 269 publications

References 46 publications

Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study

Thieny/Furanyl-hydroxyphenylpropenones as Inhibitors of LPS-induced ROS and NO Production in RAW 264.7 Macrophages, and Their Structure-Activity Relationship Study

In vitro structure-toxicity relationship of chalcones in human hepatic stellate cells

Conformational Analysis, Experimental and GIAO-DFT 13C NMR Chemical Shift Calculation on 2’-Hydroxy-3,4,5-trimethoxy-chalcone

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