Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives

Wang, Peiyi; Zhou, Longhu; Zhou, Jian; Wu, Zhibing; Xue, Wei; Song, Baoan; Yang, Song

doi:10.1016/j.bmcl.2016.01.029

Cited by 103 publications

(75 citation statements)

References 27 publications

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“…However, the application of these traditional viricides and bactericides are limited by their negative impacts on the environment and the rapid emergence of resistance. [7][8][9] Thus, exploring novel lead compounds with potent agricultural bioactivities is very crucial in the agricultural chemistry. 10 Recent works have emphasized that the skeleton of chalcones has structural characteristics typical of diaryl enone scaffold, and are an important class of natural and synthetic bioactive compounds, which exhibit a broad spectrum of pharmacological activities, [11][12][13][14][15] including antifungal, 16 antibacterial, 17 antiviral, 18 inhibitors, 19 anticancer, 20 antiparasitic, 21 anti-Alzheimer's disease, 22 antitrichomonal, 23 anti-trypanosoma cruzi 24 activities.…”

Section: Introductionmentioning

confidence: 99%

Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

Xu¹,

Su²,

Chen³

et al. 2019

RSC Adv.

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Section: Introductionmentioning

confidence: 99%

Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

Xu¹,

Su²,

Chen³

et al. 2019

RSC Adv.

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“…The rational use of agrochemicals plays a pivotal role in agricultural production by effectively controlling plant diseases [ 1 , 2 ]. Unfortunately, the application of traditional pesticides is greatly limited due to their negative impacts on the environment and the rapid emergence of resistance [ 2 , 3 ]. Therefore, searching for high-efficiency and environmentally friendly agrochemicals remains an arduous challenge in pesticide chemistry [ 1 , 4 ].…”

Section: Introductionmentioning

confidence: 99%

Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold

Zhong

Wang

Chen

et al. 2017

Chemistry Central Journal

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BackgroundMyricetin and 1,3,4-thiadiazole derivatives were reported to exhibit favorable antiviral and antibacterial activities. Aiming to discover novel myricetin analogues with potent activities, a series of novel myricetin derivatives containing 1,3,4-thiadiazole moiety were synthesized, and their antibacterial and antiviral activities were evaluated.ResultBioassay results indicated that some target compounds exhibited potential antibacterial and antiviral activities. Among them, compounds 2, 3a, 3b, 3d, 3f, 3i, 3m and 3p exhibited excellent antibacterial activities against Xanthomonas oryzae pv. Oryzae (Xoo), with EC50 values of 42.7, 38.6, 20.8, 12.9, 22.7, 27.3, 18.3 and 29.4 μg/mL, respectively, which were better than that of thiadiazole-copper (94.9 μg/mL). Compounds 3b, 3d, 3e, 3f, 3i and 3o showed good antibacterial activities against Ralstonia solanacearum (Rs), with EC50 values of 37.9, 72.6, 43.6, 59.6, 60.6 and 39.6 μg/mL, respectively, which were superior to that of thiadiazole-copper (131.7 μg/mL). In addition, compounds 3d, 3f, 3i and 3m showed better curative activities against tobacco mosaic virus (TMV), with EC50 values of 152.8, 99.7, 127.1, and 167.3 μg/mL, respectively, which were better than that of ningnanmycin (211.1 μg/mL).ConclusionsA series of myricetin derivatives containing 1,3,4-thiadiazole scaffold were synthesized, and their antibacterial activities against Xoo and Rs and their antiviral activity against TMV were evaluated. Bioassays indicated that some target compounds exhibited potential antibacterial and antiviral activities. These results indicated this kind of myricetin analogues could be further studied as potential alternative templates in the search for novel antibacterial and antiviral agents.Electronic supplementary materialThe online version of this article (doi:10.1186/s13065-017-0336-7) contains supplementary material, which is available to authorized users.

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“…However, the application of many currently available antibacterial agents is compromised by their low efficiency, phytotoxic effect and high accumulation in the soil [ 6 , 7 ]. For example, Bismerthiazol, one of the major bactericides for the control of rice bacterial leaf blight, only shows the control efficiency of 25.49% at a high dosage of 200 μg/mL [ 8 ]. Furthermore, the emergence of bactericide resistance [ 9 , 10 ] coupled with above drawbacks has led to the rising need for development of high-efficient bactericides to effectively control those agricultural diseases.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety

Zhou

Liao

et al. 2016

Molecules

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Sulfones are one of the most important classes of agricultural fungicides. To discover new lead compounds with high antibacterial activity, a series of new sulfone derivatives were designed and synthesized by introducing the aroxymethyl moiety into the scaffold of 1,3,4-oxadiazole/thiadiazole sulfones. Antibacterial activities against three phytopathogens (Xanthomonas oryzae pv. oryzae, Ralstonia solanacearum, Xanthomonas axonopodis pv. citri.) were assayed in vitro. As compared to the control of commercial fungicides and some reported sulfone fungicides, seven compounds 5I-1–5I-7 exerted remarkably higher activities with EC50 values ranging from 0.45–1.86 μg/mL against X. oryzae and 1.97–20.15 μg/mL against R. solanacearum. Exhilaratingly, 5I-1, 5I-2 and 5I-4 displayed significant in vivo activity against X. oryzae with protective effect of 90.4%, 77.7%, and 81.1% at 200 μg/mL, respectively, much higher than that exhibited by Bismerthiazol (25.6%) and Thiadiazole-copper (32.0%). And the differential phytotoxicity of active derivatives was preliminarily checked. The results demonstrated that derivative of 2-aroxymethyl-1,3,4-oxadiazole/thiadiazole sulfone can serve as potential alternative bactericides for the management of plant bacterial diseases.

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Synthesis and antibacterial activity of pyridinium-tailored 2,5-substituted-1,3,4-oxadiazole thioether/sulfoxide/sulfone derivatives

Cited by 103 publications

References 27 publications

Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

Novel chalcone derivatives containing a 1,2,4-triazine moiety: design, synthesis, antibacterial and antiviral activities

Synthesis and biological activity of myricetin derivatives containing 1,3,4-thiadiazole scaffold

Synthesis and Antibacterial Evaluation of New Sulfone Derivatives Containing 2-Aroxymethyl-1,3,4-Oxadiazole/Thiadiazole Moiety

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