Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties

Ruan, Xianghui; Zhang, Cheng; Jiang, Shichun; Guo, Tao; Xia, Rongjiao; Chen, Ying; Xu, Tao

doi:10.3390/molecules23123132

Cited by 29 publications

(27 citation statements)

References 26 publications

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“…Intermediates 1-4 were prepared according to previous methods using myricitrin and iodomethane as substrates. [27][28][29][30] Four steps were used in this process (Scheme 1). This method is provided in Appendix S1.…”

Section: Chemical Synthesis 221 General Procedures For Preparing Inmentioning

confidence: 99%

“…Those that have been undertaken have been concentrated on myricetin itself. Results from our previous investigations have highlighted that some myricetin derivatives have good biological activity in medicine and pesticides …”

Section: Introductionmentioning

confidence: 99%

“…Results from our previous investigations have highlighted that some myricetin derivatives have good biological activity in medicine and pesticides. [27][28][29] To aid the development of novel highly active compounds, we used myricitrin as the raw material, into which the active group piperidine was introduced. This substance was then combined with sulfonyl chloride to form a series of novel myricetin derivatives containing a sulfonamide moiety as an active antibacterial agent.…”

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas axonopodis pv. Citri and Ralstonia solanacearum of novel myricetin derivatives containing sulfonamide moiety

Jiang¹,

Xu²,

Chen³

et al. 2019

Pest Management Science

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BACKGROUND Myricetin and sulfonamide derivatives exhibited a wide variety of biological activity. In order to develop highly bioactive molecules, novel myricetin derivatives containing sulfonamide moiety were synthesized and antibacterial activities were investigated. RESULTS The results of bioassays indicated that compound A12, having an EC50 value of 4.7 μg mL−1, exhibited the best in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (X. oryzae pv. o.); EC50 values for this compound were even better than those of thiodiazole‐copper (TC, 71.4 μg mL−1) and bismerthiazol (BT, 54.7 μg mL−1). Compound A2, having an EC50 value of 1.1 μg mL−1, exhibited the best in vitro antibacterial activities against Xanthomonas axonopodis pv. citri (X. axonopodis pv. c); values were notably better than those of TC (60.0 μg mL−1) and BT (48.9 μg mL−1). Scanning electron microscopy analysis indicated that compounds A2 and A12 caused the cell membranes of X. axonopodis pv. c and X. oryzae pv. o. to break or deform, respectively. When the concentration of compound A12 was 100 μg mL−1, the effective curative activity against bacterial leaf blight of rice was 44.2% in vivo and the effective protection activity was 58.2% in vivo, results that were both better than values for TC (18.9 and 21.4%, respectively) and BT (12.5 and 12.5%, respectively). CONCLUSION Novel myricetin derivatives containing a sulfonamide moiety were synthesized and bioassay results showed that compounds A2 and A12 exhibited the best antibacterial activities. © 2019 Society of Chemical Industry

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Section: Chemical Synthesis 221 General Procedures For Preparing Inmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Design, synthesis and antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas axonopodis pv. Citri and Ralstonia solanacearum of novel myricetin derivatives containing sulfonamide moiety

Jiang¹,

Xu²,

Chen³

et al. 2019

Pest Management Science

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“…The turbidity method was used to test the target compounds with Xac, Xac, Rs using commercial bismerthiazol and thiodiazole copper as positive control agents . Prepare a sterile nutrient broth culture medium: 3.0 g beef extract, 5.0 g peptone, 1.0 g of yeast powder, 10.0 g of glucose and 1000 mL of secondary water, pH 7.0–7.2.…”

Section: Methodsmentioning

confidence: 99%

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Guo

Xia

Liu

et al. 2020

Chemistry & Biodiversity

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A series of novel chalcone malonate derivatives were synthesized and their antibacterial and antiviral activities were evaluated. All target compounds were characterized by spectral data. The results of antimicrobial bioassay showed that one compound (diethyl [3-(naphthalen-2-yl)-1-(3-nitrophenyl)-3-oxopropyl]propanedioate) showed excellent antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo), with an EC 50 value of 10.2 μg/mL, which is significantly superior to bismerthiazol (71.7 μg/mL) and thiodiazole copper (97.8 μg/mL). At the same time, the mechanism of two compounds was confirmed by scanning electron microscopy. In addition, another compound (diethyl [3-(naphthalen-2-yl)-1-(4-nitrophenyl)-3-oxopropyl]propanedioate) showed significant curative activity to tobacco mosaic virus, with a value of 74.3 %, which was superior to 53.3 % of ningnanmycin. The results of microscale thermophoresis also showed that the Kd value of the combination of two compounds with the coat protein of tobacco mosaic virus was 0.211 and 0.166 μmol/L, which was better than 0.596 μmol/L of ningnanmycin. At the same time, the molecular docking of two compounds with tobacco mosaic virus-coat protein shows that the compound is well embedded in the pocket between the two subunits of tobacco mosaic virus-coat protein. These results show that chalcone derivatives containing malonate group can be considered as activators in the design of antibacterial and antiviral agents.

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“…The antibacterial activities of the target compounds 3a-3r against two phytopathogenic bacterial (Xoo and Xac) were tested in vitro by the turbidimeter test [31][32][33]. Commercial agricultural antibacterial TC and BT were used as references, as shown in Table 1.…”

Section: Antibacterial Activity Of Title Compounds Against Xoo and Xamentioning

confidence: 99%

Design, Synthesis, and Biological Activity of Novel penta-1,4-dien-3-one Derivatives Containing a <em>H</em>-phosphonate Scaffold

Chen¹,

Guo²,

Xia³

et al. 2018

Preprint

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A series of penta-1,4-dien-3-one containing a H-phosphonate scaffold were designed and synthesized. The structures of all title compounds were determined by 1H-NMR, 13C-NMR, 31P-NMR, and HRMS. Bioassay results showed that several of the title compounds exhibited remarkable antibacterial and antiviral activities. Among these, compounds 3c and 3o exhibited substantial antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac). In addition, compounds 3c, 3f, and 3r showed remarkable curative activities against tobacco mosaic virus (TMV), with 50% effective concentration (EC50) values of 290.0, 234.0, and 373.6 μg/mL, respectively. These were superior to that of ningnanmycin (386.2 μg/mL). Compound 3r exhibited comparative protective activity against TMV, with an EC50 value of 291.1 μg/mL, which was better than that of ningnanmycin (297.1 μg/mL). Notably, the solubility of all title compounds improved relative to the lead compound curcumin. These results suggest that penta-1,4-dien-3-one containing a H-phosphonate scaffold may be considered as an activator for antibacterial and antiviral agents.

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Design, Synthesis, and Biological Activity of Novel Myricetin Derivatives Containing Amide, Thioether, and 1,3,4-Thiadiazole Moieties

Cited by 29 publications

References 26 publications

Design, synthesis and antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas axonopodis pv. Citri and Ralstonia solanacearum of novel myricetin derivatives containing sulfonamide moiety

Design, synthesis and antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas axonopodis pv. Citri and Ralstonia solanacearum of novel myricetin derivatives containing sulfonamide moiety

Synthesis, Biological Activity and Action Mechanism Study of Novel Chalcone Derivatives Containing Malonate

Design, Synthesis, and Biological Activity of Novel penta-1,4-dien-3-one Derivatives Containing a <em>H</em>-phosphonate Scaffold

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