Design, Synthesis, and Evaluation of New Sulfone Derivatives Containing a 1,3,4-Oxadiazole Moiety as Active Antibacterial Agents

Li, Pei; Hu, Deyu; Xie, Dandan; Chen, Jixiang; Jin, Linhong; Song, Baoan

doi:10.1021/acs.jafc.7b06061

Cited by 134 publications

(147 citation statements)

References 32 publications

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“…In this context, 1,3,4‐oxadiazole derivatives are one of the most important heterocyclic compounds that have received considerable attention over the past years. Compounds containing this nucleus have diverse pharmacological properties such as antifungal, antioxidant, antibacterial, antitubercular and anticonvulsant . Moreover, 1,3,4‐oxadiazoles are well known as efficient amide and/or ester bioisosteres which enhance the biological responses by participating in hydrogen bonding interactions with different receptors…”

Section: Introductionmentioning

confidence: 99%

Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and In Silico Molecular Modeling Studies

et al. 2020

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A number of pantoprazole derivatives were synthesized and screened for their urease inhibitory properties. Some of them showed potent inhibitions against jack bean urease. All compounds showed varying degree of IC 50 in the range of 25.85 to 181 μMol as compared to standard acetohydroxamic acid (AHA) (100 � 2.02 μMol). Derivatives bearing 5-aryl-1,3,4oxadiazole ring substitutions (aryl = pyrazyl, pyridyl and phenyl) were found to be more potent inhibitors than AHA and pantoprazole. The most promising compound, 2-((3,4-dimethoxypyridin-2-yl)methylthio)-5-(pyrazin-2-yl)-1,3,4-oxadiazole 12, with IC 50 value of 25.85 � 1.21 showed remarkable urease inhibition activity. In silico molecular modeling investigation performed to rationalize the possible binding interaction and ADME properties of compounds over the active site of urease enzyme. The induced fit docking study showed that compound 12 interacted with conserved residues His593 and Arg609 located at the mouth of the urease active site flap and are essential for enzyme catalytic activity. These target compounds could be further studied as a lead skeleton for discovery of novel urease inhibitors.[a] Dr.

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Section: Introductionmentioning

confidence: 99%

Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and In Silico Molecular Modeling Studies

et al. 2020

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“…Chemical control is one of the most important measures to prevent disease . However, long‐term use of existing traditional chemical fungicides has not only resulted in bacteria being selected for resistance, they also adversely affect the environment and plant health . It is therefore important to discover and develop novel antibacterial agents that possess a novel mechanism of action.…”

Section: Introductionmentioning

confidence: 99%

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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“…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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Design, Synthesis, and Evaluation of New Sulfone Derivatives Containing a 1,3,4-Oxadiazole Moiety as Active Antibacterial Agents

Cited by 134 publications

References 32 publications

Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and In Silico Molecular Modeling Studies

Pantoprazole Derivatives: Synthesis, Urease Inhibition Assay and In Silico Molecular Modeling Studies

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

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