Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents

Bandgar, B. P.; Gawande, Shrikant S.; Bodade, Ragini G.; Totre, Jalinder V.; Khobragade, Chandrahasya N.

doi:10.1016/j.bmc.2009.11.066

Cited by 275 publications

(143 citation statements)

References 28 publications

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“…Various methoxylated or hydroxylated chalcones, natural and synthetic, have already been tested for their possible role as anti-inflammatory agents 34,35 . Recently, we have also reported some simple methoxylated chalcones and N-phenyl pyrazole chalcones showed significant anti-inflammatory, antioxidant and antimicrobial activities 36,37 . The combination of both the active scaffolds, pyrazole and chalcone, may provide synergistic effect to improve the antiinflammatory activity.…”

Section: Introductionmentioning

confidence: 99%

Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

Chavan

Adsul

Kotmale

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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A series of novel pyrazole-based chalcones have been designed, synthesized from 1-methyl-5-(2,4,6-trimethoxyphenyl)-1H-pyrazole (6). The structures of regioisomers 6 and 7 were determined by 2D The newly synthesized compounds were tested for their inhibitory activity against COX-1 and COX-2 using an in vitro cyclooxygenase (COX) inhibition assay. Moreover, they were investigated in vivo for their anti-inflammatory activities using carrageenan-induced rat paw edema model for acute inflammation and cotton pellet-induced granuloma model for chronic inflammation. All the synthesized compounds showed potential to demonstrate anti-inflammatory activities, of particular interest compounds 10i, 10e, 10f, and 10h were found to be potent anti-inflammatory agents.

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Section: Introductionmentioning

confidence: 99%

Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

Chavan

Adsul

Kotmale

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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“…Additionally, 2'-hydroxycinnamaldehyde and the analogue 2'-benzoyloxycinnamaldehyde induce apoptosis in cancer cells via the induction of cellular reactive oxygen species (ROS) [18]. Recently antitumor activities of various cinnamic acid derivatives were explored by many research groups [19][20][21][22].…”

Section: Introductionmentioning

confidence: 99%

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

et al. 2014

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Cinnamic acids have been identified as interesting compounds with antioxidant, anti-inflammatory and cytotoxic properties. In the present study, simple cinnamic acids were synthesized by Knoevenagel condensation reactions and evaluated for the above biological activities. Compound 4ii proved to be the most potent LOX inhibitor. Phenylsubstituted acids showed better inhibitory activity against soybean LOX, and it must be noted that compounds 4i and 3i with higher lipophilicity values resulted less active than compounds 2i and 1i. The compounds have shown very good activity in different antioxidant assays. The antitumor properties of these derivatives have been assessed by their 1/IC 50 inhibitory values in the proliferation of HT-29, A-549, OAW-42, MDA-MB-231, HeLa and MRC-5 normal cell lines. The compounds presented low antitumor activity considering the IC 50 values attained for the cell lines, with the exception of compound 4ii. Molecular docking studies were carried out on cinnamic acid derivative 4ii and were found to be in accordance with our experimental biological results.

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“…The antioxidant activity studies showed that the dimethoxychalcone 5a and the corresponding dihydropyrazole 6a exhibited the highest activities which support data obtained from literature. 10 While, the anti-inflammatory activity studies showed that monomethoxychalcone 5d displayed good anti-inflammatory activity (54-62%), and the corresponding dihydropyrazoles 6d showed excellent anti-inflammatory activity (64-74%) comparable to that of celecoxib (32-78%). In addition, the docking experiments showed that compounds 5d and its cyclized derivative 6d better fit into the COX-2 active site, which was in parallel correlation with the in vitro COX inhibition evaluation.…”

Section: Resultsmentioning

confidence: 97%

“…In addition, Padhye et al 9 observed that fluorination of chalcones enhances the biological activities as shown in the reported fluorinated 2 0 -hydroxychalcones (1). In addition, promising anti-inflammatory and antioxidant activities of 2,4-dimethoxy and 3,4,5-trimethoxy chalcones (2) were obtained 10 . Cyclization of the chalcones with hydrazine hydrate will yield the corresponding dihydropyrazole derivatives, which retain the geometry of the two aromatic rings separated with three bonds like chalcones.…”

Section: Introductionmentioning

confidence: 93%

Synthesis, characterization and biological evaluation of novel 4′-fluoro-2′-hydroxy-chalcone derivatives as antioxidant, anti-inflammatory and analgesic agents

Abdellatif

Elshemy

Salama

et al. 2014

Journal of Enzyme Inhibition and Medicinal Chemistry

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In an effort to develop safe and potent anti-inflammatory agents, a series of novel 4 0 -fluoro-2 0 -hydroxychalcones 5a-d and their dihydropyrazole derivatives 6a-d was prepared. It was synthesized via aldol condensation of 4 0 -fluoro-2 0 -hydroxyacetophenone with appropriately substituted aldehydes followed by cyclization with hydrazine hydrate. All the synthesized compounds were evaluated for their antioxidant, anti-inflammatory, cyclooxygenase inhibition selectivity and analgesic activities. The dimethoxychalcone 5a and its dihydropyrazole derivative 6a showed the highest antioxidant activity, while the monomethoxychalcone 5d and its dihydropyrazole derivative 6d showed the highest analgesic and anti-inflammatory activities. It was also found that there is a close correlation between 4 0 -fluoro-2 0 -hydroxychalcones 5a-d and their dihydropyrazole derivatives 6a-d in the screened biological activities. To explain the correlation between the synthesized chalcones and their dihydropyrazole derivatives, especially for the anti-inflammatory activity, docking studies were performed.

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Synthesis and biological evaluation of simple methoxylated chalcones as anticancer, anti-inflammatory and antioxidant agents

Cited by 275 publications

References 28 publications

Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

Design, synthesis, characterization andin vitroandin vivoanti-inflammatory evaluation of novel pyrazole-based chalcones

Novel Cinnamic Acid Derivatives as Antioxidant and Anticancer Agents: Design, Synthesis and Modeling Studies

Synthesis, characterization and biological evaluation of novel 4′-fluoro-2′-hydroxy-chalcone derivatives as antioxidant, anti-inflammatory and analgesic agents

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