Design, Synthesis, and Bioactivity of α‑Ketoamide Derivatives Bearing a Vanillin Skeleton for Crop Diseases

• Published in: Journal of agricultural and food chemistry Vol. 68; no. 27; pp. 7226 - 7234
• Main Authors: Luo, Dexia, Guo, Shengxin, He, Feng, Chen, Shunhong, Dai, Ali, Zhang, Renfeng, Wu, Jian
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 08.07.2020; Amer Chemical Soc
• Subjects: Agriculture; Agriculture, Multidisciplinary; Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Anti-Bacterial Agents - pharmacology; antibacterial properties; Antiviral Agents - chemical synthesis; Antiviral Agents - chemistry; Antiviral Agents - pharmacology; Bacteria - drug effects; Bacteria - growth & development; Benzaldehydes - chemistry; Benzaldehydes - pharmacology; Chemistry; Chemistry, Applied; coat proteins; copper; Drug Design; food chemistry; Food Science & Technology; Functional Structure/Activity Relationships; Life Sciences & Biomedicine; Microbial Sensitivity Tests; Molecular Docking Simulation; pesticides; Physical Sciences; Plant Diseases - microbiology; Plant Diseases - virology; Science & Technology; Tobacco Mosaic Virus - drug effects; Tobacco Mosaic Virus - growth & development; transmission electron microscopy; vanillin; viruses; synthesis; molecular docking; bioactivity; mechanism; α-ketoamide; vanillin; alpha-ketoamide; TOBACCO-MOSAIC-VIRUS; MOIETY; PROTEIN; ANTIBACTERIAL ACTIVITY; ANTIVIRAL ACTIVITY; FLUORINE; CARCINOMA
• ISSN: 0021-8561; 1520-5118; 1520-5118
• DOI: 10.1021/acs.jafc.0c00724

A series of novel α-ketoamide derivatives bearing a vanillin skeleton were designed and synthesized. Bioactivity tests on virus and bacteria were performed. The results indicated that some compounds exhibited excellent antitobacco mosaic virus (TMV) activities, such as compound 34 exhibited an inactivation activity of 90.1% and curative activity of 51.8% and compound 28 exhibited a curative activity of 54.8% at 500 μg mL–1, which is equivalent to that of the commercial ningnanmycin (inactivation of 91.9% and curative of 51.9%). Moreover, the in vitro antibacterial activity test illustrated that compounds 2, 22, and 33 showed much higher activities than commercial thiodiazole copper, which could be used as lead compounds or potential candidates. The findings of transmission electron microscopy and molecular docking indicated that the synthesized compounds exhibited strong and significant binding affinity to the TMV coat protein and could obstruct the self-assembly and increment of TMV particles. This study revealed that α-ketoamide derivatives bearing a vanillin skeleton could be used as a novel potential pesticide for controlling the plant diseases.