Synthesis and antibacterial activity of four natural chalcones and their derivatives

Li, Yuanyuan; Sun, Bingxia; Zhai, Jiadai; Fu, Lin; Zhang, Shuxin; Zhang, Jing; Liu, Hongliang; Xie, Wenhai; Deng, Hongkuan; Chen, Zhiwei; Feng, Suying

doi:10.1016/j.tetlet.2019.151165

Cited by 20 publications

(18 citation statements)

References 23 publications

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“…Chalcones are pioneer bioactive compounds in natural products as flavonoids which, are classified α, β-Unsaturated ketones (Li et al, 2019). They occupy an extensive range of pharmacological properties as cytotoxicity on different cancer cell lines, anti-inflammatory (Gaonkar & Vignesh, 2017;Suwito et al, 2014;Nakhjavani et al, 2014), anti-diabetic agents (Hsieh et al, 2012), antimalarial (Domínguez et al, 2005), antimicrobial agents (Choudhary & Juyal, 2011;Gupta & Jain, 2015), antibacterial and antifungal (Andrade et al, 2018;Chu et al, 2018;Dan & Dai, 2020).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and evaluating antimicrobial activity for chalcones thiophen compounds

Hassan

Hussein

2022

ijhs

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This research included the preparation and characterization of compounds containing chalcones, Schiff bases, and Azo dye: bearing thiophene ring. The compounds (1mk-3mk) had prepared from the reaction acetophenone derivatives with 2-formyl thiophene and, then 2mmk had introduced in two reactions: first, its reaction with some substitutes of benzaldehyde to prepare Schiff bases (4mk-7mk), and the second was the design of a bis azo dye from p-Phenylenediamine with salicylaldehyde to get 8mk, and then reacted with chalcone 2mk to obtain the compound 9mk. The chemical formulas of the prepared compounds were confirmed by spectroscopic methods using UV, infrared, NMR spectroscopy of protons and carbon 13. The antimicrobial activity had tested against Staphylococcus aureus and Candida albicans in compared with neomycin sulfate and nystatin, and some compounds showed good to moderate inhibition at a concentration of 7.5,10 mg/ml.

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Section: Introductionmentioning

confidence: 99%

Synthesis and evaluating antimicrobial activity for chalcones thiophen compounds

Hassan

Hussein

2022

ijhs

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“…Considering the slightly greater cytotoxic activities of sanjuanolide, we completed the first synthesis and preliminary structure-activity relationship of sanjuanolide and its eight analogs (Zhai et al, 2019). Then, the total synthesis and antibacterial activities of natural chalcones bearing the 3′hydroxyisoprenyl (Li et al, 2019) moiety were also investigated in our laboratory.…”

Section: Introductionmentioning

confidence: 99%

“…Our previous studies suggest that the hydroxyisoprenyl moiety has a positive effect on their antibacterial activity (Li et al, 2019). As the basic structural unit of many biological active natural products, heterocyclic aromatic (Zheng et al, 2011;Lagu et al, 2020) and phenolic hydroxyl (Yang et al, 2007;Ammaji et al, 2022) derivatives have been used in the structural modification of chalcones several times, and the existence of these special units in chalcone derivatives is critical (Ohkuma et al, 2008;Kasetti et al, 2021).…”

Section: Introductionmentioning

confidence: 99%

Structural modification and antibacterial property studies of natural chalcone sanjuanolide

Zhai

Li²,

Fu³

et al. 2022

Front. Chem.

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Clinical infections arise from multidrug-resistant bacteria and pose a serious threat to human and global public health. Moreover, due to very few antibiotics being discovered, there is an urgent need to develop new antibacterial agents to combat antimicrobial resistance challenges. In this study, a series of new chalcone derivatives bearing a 3′-hydroxyisoprenyl moiety were prepared to employ Claisen–Schmidt condensation as a key step by combinatorial chemistry, and overall yields of these novel derivatives are in the range of 28–68% in the two-step reaction. Sanjuanolide and the synthesized derivatives have been investigated for their expected antibacterial activities against Gram-positive bacteria (Staphylococcus aureus CMCC 26003) and Gram-negative bacteria (Escherichia coli CMCC 44102). Among these compounds, only 4c (MIC = 12.5 μg/ml) and 4d (MIC = 25 μg/ml) exhibited antibacterial activity comparable to sanjuanolide (MIC = 12.5 μg/ml, against S. aureus CMCC 26003), and the results of subsequent in vivo experiments on sanjuanolide suggest that sanjuanolide exhibits bacteriostatic and bactericidal effects by altering the cellular structure, disrupting the integrity of cell membranes, and reducing the outer membrane potential.

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“…Chalcones (1,3-diphenyl-2-propen-1-one) are one of the most important classes of flavonoid compounds present in fruits, vegetables, and tea [102] and represent biogenetic precursors of flavonoids and isoflavonoids [103]. They are lipophilic phytochemicals composed of two aromatic residues (an aldehyde and an acetophenone) joined by an α, β-unsaturated carbonyl system of three carbon atoms (Figure 2) [102,104]. α, β-unsaturated carbonyl group is a good Michael acceptor and participates in nucleophilic additions [105].…”

Section: Introductionmentioning

confidence: 99%

Anticancer Activity of Natural and Synthetic Chalcones

Constantinescu

Lungu²

2021

IJMS

103

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Cancer is a condition caused by many mechanisms (genetic, immune, oxidation, and inflammatory). Anticancer therapy aims to destroy or stop the growth of cancer cells. Resistance to treatment is theleading cause of the inefficiency of current standard therapies. Targeted therapies are the most effective due to the low number of side effects and low resistance. Among the small molecule natural compounds, flavonoids are of particular interest for theidentification of new anticancer agents. Chalcones are precursors to all flavonoids and have many biological activities. The anticancer activity of chalcones is due to the ability of these compounds to act on many targets. Natural chalcones, such as licochalcones, xanthohumol (XN), panduretin (PA), and loncocarpine, have been extensively studied and modulated. Modification of the basic structure of chalcones in order to obtain compounds with superior cytotoxic properties has been performed by modulating the aromatic residues, replacing aromatic residues with heterocycles, and obtaining hybrid molecules. A huge number of chalcone derivatives with residues such as diaryl ether, sulfonamide, and amine have been obtained, their presence being favorable for anticancer activity. Modification of the amino group in the structure of aminochalconesis always favorable for antitumor activity. This is why hybrid molecules of chalcones with different nitrogen hetercycles in the molecule have been obtained. From these, azoles (imidazole, oxazoles, tetrazoles, thiazoles, 1,2,3-triazoles, and 1,2,4-triazoles) are of particular importance for the identification of new anticancer agents.

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Synthesis and antibacterial activity of four natural chalcones and their derivatives

Cited by 20 publications

References 23 publications

Synthesis and evaluating antimicrobial activity for chalcones thiophen compounds

Synthesis and evaluating antimicrobial activity for chalcones thiophen compounds

Structural modification and antibacterial property studies of natural chalcone sanjuanolide

Anticancer Activity of Natural and Synthetic Chalcones

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