Novel Ferulic Amide Ac6c Derivatives: Design, Synthesis, and Their Antipest Activity

Zhang, Renfeng; Guo, Shengxin; Deng, Peizhen; Ya, Wang; Dai, Ali; Wu, Jian

doi:10.1021/acs.jafc.1c03892

Cited by 19 publications

(17 citation statements)

References 49 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%

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%

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

Dai

Huang

et al. 2022

BMC Chemistry

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“…Compared with commercially available compounds, some ferulic amides displayed excellent antibacterial activities. 29,30 In our published work, 31 we found that some ferulic amide Ac6c derivatives showed excellent antipest activity. Encouraged by this, we envisage changing cyclohexane to cyclopentane to expand our research and develop new lead compounds, which have high levels of biological activity.…”

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confidence: 91%

Design, Synthesis, and Biological Activity of Novel Ferulic Amide Ac5c Derivatives

et al. 2021

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A total of 34 novel ferulic amide Ac5c derivatives were designed and synthesized and their antipest activities were investigated. The results showed that some compounds exhibited excellent in vitro antibacterial activity against Xanthomonas oryzae pv. oryzae (Xoo) and X. oryzae pv. oryzicola (Xoc), such as compounds 4q and 5n demonstrated excellent in vitro activity against Xoo, with EC 50 values of 4.0, and 1.9 μg/ mL, respectively. Compounds 4c, 4h, 4m, 4p, 4q, and 5a had significant in vitro activities against Xoc, with EC 50 values of 12.5, 13.9, 9.8 15.0, 9.2, and 19.8 μg/mL, respectively. Moreover, the antibacterial activity in vivo against rice bacterial leaf blight was also evaluated. Scanning electron microscopy (SEM) showed that compound 5n significantly reduced the cell membrane of Xoo, and resulted in cell surface wilting, deformation, breakage, and increased porous attributes. In addition, some of the target compounds also showed moderate biological activity against fungi and acted as potential insecticides.

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“…Natural products (NPs) not only possess diverse structures and pharmacological properties but also have unique effects, easy degradation, or good compatibility with the environment. − They have been used by humans as dyes, food additives, drugs, and pesticides for thousands of years. In recent years, the development of NP-based pesticides has become a hot topic. − Osthole ( 1 , Figure ) is a naturally occurring coumarin compound found mainly in Apiaceae (Umbelliferae) and Brassicaceae plants . It is highly abundant in the ripe fruit of Cnidium monnieri (L.) Cusson, which is commonly used as a traditional Chinese medicine .…”

Section: Introductionmentioning

confidence: 99%

Design, Synthesis, and Biological Evaluation of Novel Osthole-Based Isoxazoline Derivatives as Insecticide Candidates

Liu

Han

Yan

et al. 2022

J. Agric. Food Chem.

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Natural products are an abundant and environmentally friendly source for controlling plant pathogens and insect pests. Toward the development of new natural product-based pesticides, here, a series of osthole-based isoxazoline derivatives were prepared by [3 + 2] annulation and evaluated for their insecticidal activities and toxicities. The structures of all osthole-based isoxazoline derivatives were characterized by various spectral analyses, and derivative B13 was further confirmed by X-ray crystallography. Among all the osthole derivatives, B2 displayed the most promising growth inhibitory effect on Mythimna separata with a final corrected mortality rate of 96.4% ± 3.3, which was 1.80 times higher than those of both osthole and toosendanin. Derivative B13 displayed the most promising larvicidal activity against Plutella xylostella with an LC 50 value of 0.220 mg/mL, which was superior to rotenone. Furthermore, both B13 and B21 also exhibited better control efficacy against P. xylostella than rotenone in the pot experiments. Additionally, the toxicity evaluation suggested that these osthole-based isoxazoline derivatives showed relatively low toxicity toward nontarget organisms. Given these results, osthole derivatives B2, B13, and B21 could be deeply developed as natural insecticidal agents in agriculture.

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Novel Ferulic Amide Ac6c Derivatives: Design, Synthesis, and Their Antipest Activity

Cited by 19 publications

References 49 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

Design, Synthesis, and Biological Activity of Novel Ferulic Amide Ac5c Derivatives

Design, Synthesis, and Biological Evaluation of Novel Osthole-Based Isoxazoline Derivatives as Insecticide Candidates

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