Synthesis and antiviral activity of novel myricetin derivatives containing ferulic acid amide scaffolds

Xu, Tao; Zhang, Cheng; Chen, Mei; Xue, Yining; Liu, Tingting; Xue, Wei

doi:10.1039/c9nj05867b

Cited by 47 publications

(31 citation statements)

References 28 publications

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“…Based on the previously reported method [36][37][38], the synthetic route of target compound is listed in Scheme 1. The myricetin, anhydrous potassium carbonate and N,Ndimethylformamide (DMF) were added to a round-bottom flask with magnetic stirring; the reaction mixture was allowed to stir for 20 min at room temperature and potassium iodide was asses dropwise slowly.…”

Section: General Synthesis Procedures For Intermediate 1 and Intermedimentioning

confidence: 99%

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Zhou

Tang

et al. 2021

Monatsh Chem

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A series of myricetin derivatives containing sulfonate groups were designed and synthesized. Preliminary antibacterial activity showed that most of the target compounds exhibited significant biological activities against Xanthomonas axonopodis pv. Citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the EC50 value of compound 3e was 13.76 μg/cm3 against Xac, which was better than commercial reagents bismerthiazol (50.32 µg/cm3) and thiodiazole copper. (83.27 µg/cm3), and the EC50 value of compound 3j was 11.92 μg/cm3 against Xoo in vitro, The result was better than that of bismerthiazol (72.08 µg/cm3) and thiodiazole copper (99.26 µg/cm3). Compound 3j displayed the better in vivo activity against rice bacterial leaf blight than bismerthiazol and thiodiazole copper. Meanwhile, the antibacterial mechanism of compounds 3e and 3j was studied by scanning electron microscope (SEM). These results suggested that myricetin derivatives containing sulfonate can be considered as a new antibacterial reagents. Graphic abstract

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Section: General Synthesis Procedures For Intermediate 1 and Intermedimentioning

confidence: 99%

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Zhou

Tang

et al. 2021

Monatsh Chem

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“…trans-Ferulic acid derivatives containing acylhydrazone moiety also showed activity against tobacco mosaic virus [28] . Novel myricetin derivatives containing ferulic acid amide scaffolds were also found to be active against tobacco mosaic virus [29] . It appears that other compounds conjugated with ferulic acid may have antiviral activities.…”

Section: Resultsmentioning

confidence: 99%

in silico binding studies with b-sitosterol and some of its fatty acid esters to 3C-like protease of SARS-CoV-2

Bondhon¹,

Mahamud²,

Jannat³

et al. 2020

J. Med. Plants Stud.

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, a coronavirus (SARS-CoV-2) caused disease has turned into a pandemic with no therapeutics in the form of drugs or vaccines yet in sight. The objective of this study was to evaluate in molecular docking studies the binding energies of b-sitosterol (a phytosterol) and some of its fatty acid esters to the main protease of COVID-19, otherwise known as the 3C-like protease or 3CL pro , (PDB ID: 6LU7) in an attempt to discover possible lead compounds or drugs against the virus as a means to contain the pandemic. Molecular docking (blind) was done with the help of Autodock Vina. Seven fatty acid esters of b-sitosterol (a major phytosterol) were evaluated. While b-sitosterol gave a binding energy of -7.0 kcal/mol, b-sitosterol-acetate and b-sitosteryl-ferulate gave binding energies of -6.9 and -7.8 kcal/mol, respectively. The other esters gave lower binding energies. As a result, the ferulic acid ester of b-sitosterol has a greater probability of being a COVID-19 therapeutic.

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“…Due to the excellent features of low toxicity, the fact that it is easily synthetized and derived, and considering pyrimidine as a parent compound, the development of promising agrochemical candidates will soon become a reality. Meanwhile, amine, a key moiety in heterocyclic chemistry, play a leading role in pesticide chemistry due to their potent bioactivities including antifungal ( Cheng et al, 2020 ; Chen et al, 2021a ), antibacterial ( Chen et al, 2021a ), antiviral ( Tang et al, 2020 ), herbicidal ( Sun et al, 2020 ), and insecticidal ( Chen et al, 2021b ; Li et al, 2021b ) activities. In our previous work, we reported a series of novel pyrimidine derivatives containing an amine moiety ( Figure 1 ) and found that the target compounds revealed certain antifungal, insecticidal, and antiviral activities ( Wu et al, 2016a : Wu et al, 2020 ).…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antifungal Activity of Pyrimidine Derivatives Containing an Amide Moiety

Lan

et al. 2021

Front. Chem.

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In this study, 17 novel pyrimidine derivatives containing an amide moiety were synthesized. Then their in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phomopsis sp., and Botrytis cinereal (B. cinereal) were determined. A preliminary biological test showed that compounds 5-bromo-2-fluoro-N-(2-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)phenyl)benzamide (5f) and 5-bromo-2-fluoro-N-(3-((2-methyl-6-(trifluoromethyl)pyrimidin-4-yl)oxy)phenyl)benzamide (5o) exhibited higher antifungal activity against Phomopsis sp., with an inhibition rate of 100% compared to that of Pyrimethanil at 85.1%. In particular, compound 5o exhibited excellent antifungal activity against Phompsis sp., with the EC50 value of 10.5 μg/ml, which was even better than that of Pyrimethanil (32.1 μg/ml). As far as we know, this is the first report on the antifungal activities against B. dothidea, Phomopsis sp., and B. cinereal of this series of pyrimidine derivatives containing an amide moiety.

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Synthesis and antiviral activity of novel myricetin derivatives containing ferulic acid amide scaffolds

Abstract: A variety of myricetin derivatives bearing ferulic acid amide scaffolds were designed and synthesized.

Cited by 47 publications

References 28 publications

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

Design, synthesis, and antibacterial activity of novel myricetin derivatives containing sulfonate

in silico binding studies with b-sitosterol and some of its fatty acid esters to 3C-like protease of SARS-CoV-2

Synthesis and Antifungal Activity of Pyrimidine Derivatives Containing an Amide Moiety

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