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

2019 ◽  
Vol 76 (3) ◽  
pp. 853-860 ◽  
Author(s):  
Shichun Jiang ◽  
Xu Tang ◽  
Mei Chen ◽  
Jun He ◽  
Shijun Su ◽  
...  
Keyword(s):  
Ralstonia Solanacearum ◽  
Antibacterial Activities ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
Xanthomonas Axonopodis

scholarly journals Design, Synthesis, and Biological Activity of Novel penta-1,4-dien-3-one Derivatives Containing a H-phosphonate Scaffold

2018 ◽  
Author(s):  
Lijuan Chen ◽  
Tao Guo ◽  
Rongjiao Xia ◽  
Xu Tang ◽  
Ying Chen ◽  
...  
Keyword(s):  
31P Nmr ◽  
Antiviral Agents ◽  
Antibacterial Activities ◽  
Effective Concentration ◽  
Xanthomonas Oryzae ◽  
Protective Activity ◽  
Design Synthesis ◽  
Xanthomonas Axonopodis ◽  
Antiviral Activities ◽  
Better Than

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.

scholarly journals Novel Thiochromanone Derivatives Containing a Sulfonyl Hydrazone Moiety: Design, Synthesis, and Bioactivity Evaluation

Molecules ◽  
2021 ◽  
Vol 26 (10) ◽  
pp. 2925
Author(s):  
Lu Yu ◽  
Jiyan Chi ◽  
Lingling Xiao ◽  
Jie Li ◽  
Zhangfei Tang ◽  
...  
Keyword(s):  
Rhizoctonia Solani ◽  
Sclerotinia Sclerotiorum ◽  
13C Nmr ◽  
Inhibitory Activity ◽  
Antibacterial Activities ◽  
Gibberella Zeae ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
Xanthomonas Axonopodis ◽  
Verticillium Dahlia

A series of novel thiochromanone derivatives containing a sulfonyl hydrazone moiety were designed and synthesized. Their structures were determined by 1H-NMR, 13C-NMR, and HRMS. Bioassay results showed that most of the target compounds revealed moderate to good antibacterial activities against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri. Compound 4i had the best inhibitory activity against Xanthomonas oryzae pv. oryzae, Xanthomonas oryzae pv. oryzicolaby, and Xanthomonas axonopodis pv. citri, with the EC50 values of 8.67, 12.65, and 10.62 μg/mL, which were superior to those of Bismerthiazol and Thiodiazole-copper. Meanwhile, bioassay results showed that all of the target compounds proved to have lower antifungal activities against Sclerotinia sclerotiorum, Fusarium oxysporum, Gibberella zeae, Rhizoctonia solani, Verticillium dahlia, and Botrytis cinerea than those of Carbendazim.

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

Molecules ◽  
2018 ◽  
Vol 23 (12) ◽  
pp. 3132 ◽  
Author(s):  
Xianghui Ruan ◽  
Cheng Zhang ◽  
Shichun Jiang ◽  
Tao Guo ◽  
Rongjiao Xia ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Pathogenic Bacteria ◽  
Antibacterial Activities ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
Antiviral Activities ◽  
Potential Alternative ◽  
Better Than

A series of myricetin derivatives containing amide, thioether, and 1,3,4-thiadiazole moieties were designed and synthesized, and their antiviral and antibacterial activities were assessed. The bioassays showed that all the title compounds exhibited potent in vitro antibacterial activities against Xanthomonas citri (Xac), Ralstonia solanacearum (Rs), and Xanthomonas oryzae pv. Oryzae (Xoo). In particular, the compounds 5a, 5f, 5g, 5h, 5i, and 5l, with EC50 values of 11.5–27.3 μg/mL, showed potent antibacterial activity against Xac that was better than the commercial bactericides Bismerthiazol (34.7 μg/mL) and Thiodiazole copper (41.1% μg/mL). Moreover, the in vivo antiviral activities against tobacco mosaic virus (TMV) of the target compounds were also tested. Among these compounds, the curative, protection, and inactivation activities of 5g were 49.9, 52.9, and 73.3%, respectively, which were better than that of the commercial antiviral Ribavirin (40.6, 51.1, and 71.1%, respectively). This study demonstrates that myricetin derivatives bearing amide, thioether, and 1,3,4-thiadiazole moieties can serve as potential alternative templates for the development of novel, highly efficient inhibitors against plant pathogenic bacteria and viruses.

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

2021 ◽  
Vol 152 (3) ◽  
pp. 345-356
Author(s):  
Shijun Su ◽  
Qing Zhou ◽  
Xuemei Tang ◽  
Feng Peng ◽  
Tingting Liu ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Biological Activities ◽  
Xanthomonas Oryzae ◽  
Antibacterial Mechanism ◽  
Design Synthesis ◽  
Xanthomonas Axonopodis ◽  
Scanning Electron ◽  
Better Than

AbstractA 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

scholarly journals Design, Synthesis, and Bioactivity Evaluation of New Thiochromanone Derivatives Containing a Carboxamide Moiety

Molecules ◽  
2021 ◽  
Vol 26 (15) ◽  
pp. 4391
Author(s):  
Lingling Xiao ◽  
Lu Yu ◽  
Pei Li ◽  
Jiyan Chi ◽  
Zhangfei Tang ◽  
...  
Keyword(s):  
Antibacterial Activities ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
Compound A ◽  
Antifungal Activities ◽  
Antibacterial And Antifungal Activities ◽  
In Vitro Antibacterial Activity ◽  
Antibacterial And Antifungal ◽  
In Vitro Antifungal Activity

In this study, using the botanical active component thiochromanone as the lead compound, a total of 32 new thiochromanone derivatives containing a carboxamide moiety were designed and synthesized and their in vitro antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas oryzae pv. oryzicolaby (Xoc), and Xanthomonas axonopodis pv. citri (Xac) were determined, as well as their in vitro antifungal activities against Botryosphaeria dothidea (B. dothidea), Phomopsis sp., and Botrytis cinerea (B. cinerea). Bioassay results demonstrated that some of the target compounds exhibited moderate to good in vitro antibacterial and antifungal activities. In particular, compound 4e revealed excellent in vitro antibacterial activity against Xoo, Xoc, and Xac, and its EC50 values of 15, 19, and 23 μg/mL, respectively, were superior to those of Bismerthiazol and Thiodiazole copper. Meanwhile, compound 3b revealed moderate in vitro antifungal activity against B. dothidea at 50 μg/mL, and the inhibition rate reached 88%, which was even better than that of Pyrimethanil, however, lower than that of Carbendazim. To the best of our knowledge, this is the first report on the antibacterial and antifungal activities of this series of novel thiochromanone derivatives containing a carboxamide moiety.

Design, synthesis and characterization of copper-based coordination compounds with bidentate (N,N and N,O) ligands: reversible uptake of iodine, dye adsorption and assessment of their antibacterial properties

CrystEngComm ◽  
2019 ◽  
Vol 21 (2) ◽  
pp. 251-262 ◽  
Author(s):  
Azizolla Beheshti ◽  
Elham Sadat Mousavi Fard ◽  
Maciej Kubicki ◽  
Peter Mayer ◽  
Carmel T. Abrahams ◽  
...  
Keyword(s):  
Coordination Compounds ◽  
Copper Complexes ◽  
Antibacterial Properties ◽  
Dye Adsorption ◽  
Antibacterial Activities ◽  
Synthesis And Characterization ◽  
Design Synthesis ◽  
Iodine Adsorption

This work presents the synthesis of close-packed copper complexes with an uncommon ability for dye and iodine adsorption and antibacterial activities.

scholarly journals Synthesis and Antibacterial Evaluation of N-phenylacetamide Derivatives Containing 4-Arylthiazole Moieties

Molecules ◽  
2020 ◽  
Vol 25 (8) ◽  
pp. 1772
Author(s):  
Hui Lu ◽  
Xia Zhou ◽  
Lei Wang ◽  
Linhong Jin
Keyword(s):  
Antibacterial Agents ◽  
Antibacterial Activities ◽  
Effective Concentration ◽  
Nematicidal Activity ◽  
Xanthomonas Oryzae ◽  
Membrane Rupture ◽  
Sar Studies ◽  
Structure Activity ◽  
Antibacterial Evaluation

A series of new N-phenylacetamide derivatives containing 4-arylthiazole moieties was designed and synthesized by introducing the thiazole moiety into the amide scaffold. The structures of the target compounds were confirmed by 1H-NMR, 13C-NMR and HRMS. Their in vitro antibacterial activities were evaluated against three kinds of bacteria—Xanthomonas oryzae pv. Oryzae (Xoo), Xanthomonas axonopodis pv. Citri (Xac) and X.oryzae pv. oryzicola (Xoc)—showing promising results. The minimum 50% effective concentration (EC50) value of N-(4-((4-(4-fluoro-phenyl)thiazol-2-yl)amino)phenyl)acetamide (A1) is 156.7 µM, which is superior to bismerthiazol (230.5 µM) and thiodiazole copper (545.2 µM). A scanning electron microscopy (SEM) investigation has confirmed that compound A1 could cause cell membrane rupture of Xoo. In addition, the nematicidal activity of the compounds against Meloidogyne incognita (M. incognita) was also tested, and compound A23 displayed excellent nematicidal activity, with mortality of 100% and 53.2% at 500 μg/mL and 100 μg/mL after 24 h of treatment, respectively. The preliminary structure-activity relationship (SAR) studies of these compounds are also briefly described. These results demonstrated that phenylacetamide derivatives may be considered as potential leads in the design of antibacterial agents.

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