Trifluoromethylpyridine 1,3,4-Oxadiazole Derivatives: Emerging Scaffolds as Bacterial Agents

Yu, Gang; Chen, Shunhong; Guo, Shengxin; Xu, Bixue; Wu, Jian

doi:10.1021/acsomega.1c04472

Cited by 8 publications

(3 citation statements)

References 32 publications

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“…On the basis of previous work, the antibacterial activity of the target compounds was tested by turbidity method [ 15 , 16 , 39 ]. The preliminary results of the in vitro antibacterial activities of target compounds D1–D24 against Xoo and Xac are shown in Table 1 .…”

Section: Resultsmentioning

confidence: 99%

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Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol

Dai

Huang

et al. 2022

BMC Chemistry

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Background Plant diseases caused by viruses and bacteria cause huge economic losses due to the lack of effective control agents. New potential pesticides can be discovered through biomimetic synthesis and structural modification of natural products. A series of ferulic acid derivatives containing an β-amino alcohol were designed and synthesized, and their biological activities were evaluated. Result Bioassays results showed that the EC50 values of compound D24 against Xanthomonas oryzae pv. oryzae (Xoo) was 14.5 μg/mL, which was better than that of bismerthiazol (BT, EC50 = 16.2 μg/mL) and thiodiazole copper (TC, EC50 = 44.5 μg/mL). The in vivo curative and protective activities of compound D24 against Xoo were 50.5% and 50.1%, respectively. The inactivation activities of compounds D2, D3 and D4 against tobacco mosaic virus (TMV) at 500 μg/mL were 89.1, 93.7 and 89.5%, respectively, superior to ningnanmycin (93.2%) and ribavirin (73.5%). In particular, the EC50 value of compound D3 was 38.1 μg/mL, and its molecular docking results showed that compound D3 had a strong affinity for TMV-CP with a binding energy of − 7.54 kcal/mol, which was superior to that of ningnanmycin (− 6.88 kcal /mol). Conclusions The preliminary mechanism research results indicated that compound D3 may disrupt the three-dimensional structure of the TMV coat protein, making TMV particles unable to self-assemble, which may provide potential lead compounds for the discovery of novel plant antiviral agents. Graphical Abstract

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Section: Resultsmentioning

confidence: 99%

“…The turbidity method was used to evaluate the in vitro antibacterial activity of all target compounds against Xoo and Xac [ 15 , 39 ]. Dimethyl sulfoxide (DMSO) was used as a negative control, and the commercial bactericides thiodiazole copper ( TC ) and bismerthiozol ( BT ) were used as positive controls.…”

Section: Methodsmentioning

confidence: 99%

Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol

Dai

Huang

et al. 2022

BMC Chemistry

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“…The presence of nitrogen in the molecule is usually accompanied by the emergence of new compound activities or the enhancement of the original activity characteristics of natural terpenoids ( Lungu., 2015 ). Among them, 1,3,4-oxadiazole is a kind of heterocyclic compound with a variety of biological activities, and its derivatives show antiviral ( Gan et al, 2017 ; He et al, 2021 ), antibacterial ( Vasantha et al, 2019 ; Yu et al, 2021 ; Wang S. et al, 2021 ), antifungal ( Wen et al, 2019 ; Wang X. et al, 2021 ) and insecticidal activity ( Yang et al, 2020 ) in agricultural applications. Some also proved to be attractive anti-cancer ( Kumar et al, 2009 ), anti-depressant ( Ergun et al, 2010 ), anti-HIV ( Parizadeh et al, 2018 ), and anti-inflammatory ( Naseer et al, 2019 ) medicines.…”

Section: Introductionmentioning

confidence: 99%

1,3,4-Oxadiazole Contained Sesquiterpene Derivatives: Synthesis and Microbiocidal Activity for Plant Disease

Dai

Zheng

et al. 2022

Front. Chem.

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A series of 1,3,4-oxadiazole contained sesquiterpene derivatives were synthesized, and the activity of the target compounds against Xanthomonas oryzae pv. oryzae (Xoo), Xanthomonas axonopodis pv. citri (Xac), and tobacco mosaic virus (TMV) were evaluated. The biological activity results showed that the EC50 values of compounds H4, H8, H11, H12, H14, H16, and H19 for Xac inhibitory activity were 33.3, 42.7, 56.1, 74.5, 37.8, 43.8, and 38.4 μg/ml, respectively. Compounds H4, H8, H15, H19, H22, and H23 had inhibitory effects on Xoo, with EC50 values of 51.0, 43.3, 43.4, 50.5, 74.6, and 51.4 μg/ml, respectively. In particular, the curative and protective activities of compound H8 against Xoo in vivo were 51.9 and 49.3%, respectively. In addition, the EC50 values of the inactivation activity of compounds H4, H5, H9, H10, and H16 against TMV were 69.6, 58.9, 69.4, 43.9, and 60.5 μg/ml, respectively. The results of molecular docking indicated that compound H10 exhibited a strong affinity for TMV-coat protein, with a binding energy of −8.88 kcal/mol. It may inhibit the self-assembly and replication of TMV particles and have an anti-TMV effect, which supports its potential usefulness as an antiviral agent.

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Synthesis, carbonic anhydrase inhibition, anticancer activity, and molecular docking studies of 1,3,4-oxadiazole derivatives

et al. 2022

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Trifluoromethylpyridine 1,3,4-Oxadiazole Derivatives: Emerging Scaffolds as Bacterial Agents

Cited by 8 publications

References 32 publications

Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol

Design, synthesis, and bioactivity of ferulic acid derivatives containing an β-amino alcohol

1,3,4-Oxadiazole Contained Sesquiterpene Derivatives: Synthesis and Microbiocidal Activity for Plant Disease

Synthesis, carbonic anhydrase inhibition, anticancer activity, and molecular docking studies of 1,3,4-oxadiazole derivatives

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