scholarly journals Synthesis and Antibacterial Evaluation of Novel 1,3,4-Oxadiazole Derivatives Containing Sulfonate/Carboxylate Moiety

Molecules ◽  
2020 ◽  
Vol 25 (7) ◽  
pp. 1488
Author(s):  
Lei Wang ◽  
Xia Zhou ◽  
Hui Lu ◽  
Xianfu Mu ◽  
Linhong Jin
Keyword(s):  
Antibacterial Activity ◽  
Inhibitory Effect ◽  
Sem Analysis ◽  
Leaf Blight ◽  
Xanthomonas Oryzae ◽  
Bacterial Leaf Blight ◽  
Xanthomonas Axonopodis ◽  
Better Than

In order to discover new lead compounds with high antibacterial activity, a series of new derivatives were designed and synthesized by introducing a sulfonate or carboxylate moiety into the 1,3,4-oxadiazole structure. Antibacterial activity against two phytopathogens, Xanthomonas oryzae pv. oryzae (Xoo) and Xanthomonas axonopodis pv. citri (Xac), was assayed in vitro. The preliminary results indicated that ten compounds including 4a-1-4a-4 and 4a-11-4a-16 had good antibacterial activity against Xoo, with EC50 values ranging from 50.1-112.5 µM, which was better than those of Bismerthiazol (253.5 µM) and Thiodiazole copper (467.4 µM). Meanwhile, 4a-1, 4a-2, 4a-3 and 4a-4 demonstrated good inhibitory effect against Xanthomonas axonopodis pv. citri with EC50 values around 95.8-155.2 µM which were better than those of bismerthiazol (274.3 µM) and thiodiazole copper (406.3 µM). In addition, in vivo protection activity of compound 4a-2 and 4a-3 against rice bacterial leaf blight was 68.6% and 62.3%, respectively, which were better than bismerthiazol (49.6%) and thiodiazole copper (42.2%). Curative activity of compound 4a-2 and 4a-3 against rice bacterial leaf blight was 62.3% and 56.0%, which were better than bismerthiazol (42.9%) and thiodiazole copper (36.1%). Through scanning electron microscopy (SEM) analysis, it was observed that compound 4a-2 caused the cell membrane of Xanthomonas oryzae pv. oryzae ruptured or deformed. The present results indicated novel derivatives of 5-phenyl sulfonate methyl 1,3,4-oxadiazole might be potential antibacterial agents.

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 Antibacterial Activity of Novel Pyrimidine-Containing 4H-Chromen-4-one Derivatives

2020 ◽  
Author(s):  
Shijun Su ◽  
Mei Chen ◽  
Xuemei Tang ◽  
Feng Peng ◽  
Tingting Liu ◽  
...  
Keyword(s):  
Antibacterial Activity ◽  
Inhibitory Effect ◽  
Xanthomonas Oryzae ◽  
Design Synthesis ◽  
H Nmr ◽  
Half Maximal Effective Concentration ◽  
Bacterial Cell Membrane ◽  
Better Than ◽  
C Nmr

Abstract A series of pyrimidine-containing 4H-chromen-4-one derivatives were designed and synthesized by combining bioactive substructures. All compounds were characterized using 1H NMR, 13C NMR, 19F NMR and HRMS. Preliminary biological activity results showed that most of title compounds displayed significant inhibitory activity against Xanthomonas axonopodis pv. Citri (Xac), Xanthomonas oryzae pv. oryzae (Xoo) and Ralstonia solanacearum (Rs). In particular, compound 4c demonstrated a good inhibitory effect against Xac and Xoo, with half-maximal effective concentration(EC50) values of 15.5 and 14.9 μg/mL respectively, and that of compound 4h showed the best antibacterial activity against Rs with an EC50 value of 14.7 μg/mL, These results were better than both bismerthiazol (BT, 51.7, 70.1 and 52.7 μg/mL, respectively) and thiodiazole copper (TC, 77.9, 95.8 and 72.1 μg/mL respectively). In vivo antibacterial activity results indicated that compound 4c displayed better curative(42.4%) and protective (49.2%) activities for reducing rice bacterial leaf blight than both BT (35.2, 39.1%) and TC (30.8, 27.3%). The mechanism of compound 4c against Xoo was analysed through scanning electron microscopy (SEM). Results showed that the compound destroied the bacterial cell membrane structure. These results indicated that pyrimidine-containing 4H-chromen-4-one derivatives are valuable in the research of new agrochemicals.

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 Activity of extracellular compounds of Pseudomonas sp. against Xanthomonas axonopodis in vitro and bacterial leaf blight in eucalyptus

2012 ◽  
Vol 37 (4) ◽  
pp. 233-238 ◽  
Author(s):  
Lucilene P. Lopes ◽  
Admiltom G. Oliveira Jr ◽  
Jamile P.O. Beranger ◽  
Cíntia G. Góis ◽  
Fernanda C.S. Vasconcellos ◽  
...  
Keyword(s):  
Leaf Blight ◽  
Bacterial Leaf Blight ◽  
Pseudomonas Sp ◽  
Xanthomonas Axonopodis

scholarly journals Novel 1,3,4-Oxadiazole Derivatives Containing a Cinnamic Acid Moiety as Potential Bactericide for Rice Bacterial Diseases

2019 ◽  
Vol 20 (5) ◽  
pp. 1020 ◽  
Author(s):  
Shaobo Wang ◽  
Xiuhai Gan ◽  
Yanju Wang ◽  
Shaoyuan Li ◽  
Chongfen Yi ◽  
...  
Keyword(s):  
Cinnamic Acid ◽  
Predictive Ability ◽  
Antibacterial Activities ◽  
Leaf Blight ◽  
Bacterial Leaf Blight ◽  
Acid Moiety ◽  
Bacterial Diseases ◽  
Oxadiazole Derivatives

Rice bacterial leaf blight and leaf streak are two important bacterial diseases of rice, which can result in yield loss. Currently, effective antimicrobials for rice bacterial diseases are still lacking. Thus, to develop highly effective and low-risk bactericides, 31 novel 1,3,4-oxadiazole derivatives containing a cinnamic acid moiety were designed and synthesized. Bioassay results demonstrated that all compounds exhibited good antibacterial activities in vitro. Significantly, compounds 5r and 5t showed excellent antibacterial activities against Xanthomonas oryzae pv. oryzae (Xoo) and X. oryzae pv. oryzicola (Xoc), with the 50% effective concentration (EC50) values of 0.58 and 0.34, and 0.44 and 0.20 μg/mL, respectively. These compounds were much better than thiodiazole copper (123.10 and 161.52 μg/mL) and bismerthiazol (85.66 and 110.96 μg/mL). Moreover, compound 5t had better protective and curative activities against rice bacterial leaf blight and leaf streak than thiodiazole copper and bismerthiazol in vivo. Simultaneously, the in vivo efficacy of the compounds was demonstrated by real-time quantitative PCR to quantify bacterial titers. In addition, a three-dimensional quantitative structure–activity relationship model was created and presented good predictive ability. This work provides support for 1,3,4-oxadiazole derivatives containing a cinnamic acid moiety as a potential new bactericide for rice bacterial diseases.

scholarly journals In Vitro and In Vivo Antibacterial Activity of Some Organic and Inorganic Salts Against Asiatic Citrus Canker Agent Xanthomonas Citri Subsp. Citri

2014 ◽  
Vol 2 (6) ◽  
pp. 296
Author(s):  
Vahideh Hasabi ◽  
Hossein Askari ◽  
Seyed Mehdi Alavi ◽  
Masood Soltani Najafabadi
Keyword(s):  
Antibacterial Activity ◽  
Citrus Canker ◽  
Inhibitory Effect ◽  
Inorganic Salts ◽  
Xanthomonas Citri ◽  
Canker Disease ◽  
Growth Inhibitory ◽  
Iron And Zinc

Asiatic citrus canker caused by Xanthomonas citri subsp. citri is becoming a disease of high economic impact, affecting all types of important citrus crops. In this study, the potential antibacterial activity of ten organic and inorganic salts on X. citri subsp. citri and on citrus canker disease development was evaluated. Among the salt compounds, copper, iron and zinc inorganic salts particularly zinc (with the highest diameter of inhibition, the lowest MIC and MBC values and the highest bacterial growth inhibitory effect) had direct antibacterial activity and strongly reduced the development of canker disease and bacterial population of lime plants.

The Effect of Barbituric Acid Derivatives on Platelet Function in Vitro and in Vivo

1973 ◽  
Vol 30 (02) ◽  
pp. 315-326
Author(s):  
J. Heinz Joist ◽  
Jean-Pierre Cazenave ◽  
J. Fraser Mustard
Keyword(s):  
Platelet Aggregation ◽  
Platelet Function ◽  
Barbituric Acid ◽  
Platelet Rich Plasma ◽  
Inhibitory Effect ◽  
Primary Response ◽  
Sodium Pentobarbital ◽  
Barbituric Acid Derivatives

SummarySodium pentobarbital (SPB) and three other barbituric acid derivatives were found to inhibit platelet function in vitro. SPB had no effect on the primary response to ADP of platelets in platelet-rich plasma (PRP) or washed platelets but inhibited secondary aggregation induced by ADP in human PRP. The drug inhibited both phases of aggregation induced by epinephrine. SPB suppressed aggregation and the release reaction induced by collagen or low concentrations of thrombin, and platelet adherence to collagen-coated glass tubes. The inhibition by SPB of platelet aggregation was readily reversible and isotopically labeled SPB did not become firmly bound to platelets. No inhibitory effect on platelet aggregation induced by ADP, collagen, or thrombin could be detected in PRP obtained from rabbits after induction of SPB-anesthesia.

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