Novel amide derivatives containing an imidazo[1,2-a]pyridine moiety: Design, synthesis as potential nematicidal and antibacterial agents

Wei, Chengqian; Huang, Jun-Jie; Luo, Yuqin; Wang, Shaobo; Wu, Sikai; Xing, Zhifu; Chen, Jixiang

doi:10.1016/j.pestbp.2021.104857

Cited by 43 publications

(28 citation statements)

References 22 publications

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“…The molecular dynamic was performed using AMBER 16 [ 22 ]. The dominant conformation was confirmed by 10 ns of dynamic trajectory analysis, and the binding energy calculation was conducted via the MM–PBSA method [ 23 ].…”

Section: Methodsmentioning

confidence: 99%

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Discovery of Novel Dihydrolipoamide S-Succinyltransferase Inhibitors Based on Fragment Virtual Screening

Wei

Huang

Wang

et al. 2021

IJMS

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A series of new oxadiazole sulfone derivatives containing an amide moiety was synthesized based on fragment virtual screening to screen high-efficiency antibacterial agents for rice bacterial diseases. All target compounds showed greater bactericidal activity than commercial bactericides. 3-(4-fluorophenyl)-N-((5-(methylsulfonyl)-1,3,4-oxadiazol-2-yl)methyl)acrylamide (10) showed excellent antibacterial activity against Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicola, with EC50 values of 0.36 and 0.53 mg/L, respectively, which were superior to thiodiazole copper (113.38 and 131.54 mg/L) and bismerthiazol (83.07 and 105.90 mg/L). The protective activity of compound 10 against rice bacterial leaf blight and rice bacterial leaf streak was 43.2% and 53.6%, respectively, which was superior to that of JHXJZ (34.1% and 26.4%) and thiodiazole copper (33.0% and 30.2%). The curative activity of compound 10 against rice bacterial leaf blight and rice bacterial leaf streak was 44.5% and 51.7%, respectively, which was superior to that of JHXJZ (32.6% and 24.4%) and thiodiazole copper (27.1% and 28.6%). Moreover, compound 10 might inhibit the growth of Xanthomonas oryzae pv. oryzae and Xanthomonas oryzae pv. oryzicola by affecting the extracellular polysaccharides, destroying cell membranes, and inhibiting the enzyme activity of dihydrolipoamide S-succinyltransferase.

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Section: Methodsmentioning

confidence: 99%

“…General Procedures for the Preparation of Compounds 1 – 26 . The different oxadiazole intermediates 1a – 2a were synthesized according to known methods [ 23 ]. Different acids containing aromatic groups were added to SOCl 2 (5–8 mL) and refluxed for 5–8 h to obtain intermediates 1b – 17b .…”

Section: Methodsmentioning

confidence: 99%

Discovery of Novel Dihydrolipoamide S-Succinyltransferase Inhibitors Based on Fragment Virtual Screening

Wei

Huang

Wang

et al. 2021

IJMS

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“…incognita (parasitic on tomato plants), A. besseyi (potato dextrose agar-Botrytis cinerea breeding), B. xylophilus (potato dextrose agar-Botrytis cinerea breeding), and C. elegans (nematode growth medium-inactivated Escherichia coli OP 50 cultivation) were provided by the Fine Chemical Research and Development Center of Guizhou University (Guizhou, China). The methodology used for the nematocidal bioassays of these target compounds was modified in the light of the conventional methods reported in the previously published literature [47][48][49]. The nematicidal activity of the target compounds against four nematodes was determined using 48-well biochemical culture dishes.…”

Section: Nematicidal Activity Bioassay In Vitromentioning

confidence: 99%

Design, Synthesis and Antifungal/Nematicidal Activity of Novel 1,2,4-Oxadiazole Derivatives Containing Amide Fragments

Liu

Luo

Wang

et al. 2022

IJMS

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Plant diseases that are caused by fungi and nematodes have become increasingly serious in recent years. However, there are few pesticide chemicals that can be used for the joint control of fungi and nematodes on the market. To solve this problem, a series of novel 1,2,4-oxadiazole derivatives containing amide fragments were designed and synthesized. Additionally, the bioassays revealed that the compound F15 demonstrated excellent antifungal activity against Sclerotinia sclerotiorum (S. sclerotiorum) in vitro, and the EC50 value of that was 2.9 μg/mL, which is comparable with commonly used fungicides thifluzamide and fluopyram. Meanwhile, F15 demonstrated excellent curative and protective activity against S. sclerotiorum-infected cole in vivo. The scanning electron microscopy results showed that the hyphae of S. sclerotiorum treated with F15 became abnormally collapsed and shriveled, thereby inhibiting the growth of the hyphae. Furthermore, F15 exhibited favorable inhibition against the succinate dehydrogenase (SDH) of the S. sclerotiorum (IC50 = 12.5 μg/mL), and the combination mode and binding ability between compound F15 and SDH were confirmed by molecular docking. In addition, compound F11 showed excellent nematicidal activity against Meloidogyne incognita at 200 μg/mL, the corrected mortality rate was 93.2%, which is higher than that of tioxazafen.

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“…54, 175.87, 168.27, 161.79, 137.19, 135.98, 135.57, 132.31, 131.92, 131.67, 131.67, 131.65, 130.30, 129.95, 129.84, 129.84, 128.39, 127.57, 127.57, 126.20, 125.72, 115.39, 115.39, 61.51 (Guizhou, China). The nematocidal bioassays of these target compounds was tested based on the previous reported methods with minor modification (Wei, et al, 2021). The compound was dissolved with 50 μl DMF, and was then diluted with 1% Tween-80 to obtain 50 and 10 μg/ml concentrations.…”

Section: Preparation Procedures For the Target Compounds A1−a21 And B...mentioning

confidence: 99%

Design, Synthesis, and Biological Activity of Novel Chalcone Derivatives Containing an 1,2,4-Oxadiazole Moiety

et al. 2022

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To discover a lead compound for agricultural use, 34 novel chalcone derivatives containing an 1,2,4-oxadiazole moiety were designed and synthesized. Their nematocidal activities against Bursaphelenchus xylophilus, Aphelenchoides besseyi, and Ditylenchus dipsaci and their antiviral activities against tobacco mosaic virus (TMV), pepper mild mottle virus (PMMoV), and tomato spotted wilt virus (TSWV) were evaluated. Biological assay results indicate that compounds A13 and A14 showed good nematocidal activities against B. xylophilus, A. besseyi, and D. dipsaci, with LC50 values of 35.5, 44.7, and 30.2 μg/ml and 31.8, 47.4, and 36.5 μg/ml, respectively, which are better than tioxazafen, fosthiazate, and abamectin. Furthermore, compound A16 demonstrated excellent protective activity against TMV, PMMoV, and TSWV, with EC50 values of 210.4, 156.2, and 178.2 μg/ml, respectively, which are superior to ningnanmycin (242.6, 218.4, and 180.5 μg/ml).

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Novel amide derivatives containing an imidazo[1,2-a]pyridine moiety: Design, synthesis as potential nematicidal and antibacterial agents

Cited by 43 publications

References 22 publications

Discovery of Novel Dihydrolipoamide S-Succinyltransferase Inhibitors Based on Fragment Virtual Screening

Discovery of Novel Dihydrolipoamide S-Succinyltransferase Inhibitors Based on Fragment Virtual Screening

Design, Synthesis and Antifungal/Nematicidal Activity of Novel 1,2,4-Oxadiazole Derivatives Containing Amide Fragments

Design, Synthesis, and Biological Activity of Novel Chalcone Derivatives Containing an 1,2,4-Oxadiazole Moiety

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