Zhang Ming-Jun, Li Ming-Xu, Lu Ai-Dang, Tang Hong-Ying, Zhou Zheng-Hong, Wang Qing-Min, Wang Zi-Wen
School of Chemical Engineering and Technology, Hebei University of Technology, Tianjin, China.
Tianjin Key Laboratory of Structure and Performance for Functional Molecules, College of Chemistry, Tianjin Normal University, Tianjin, China.
Pest Manag Sci. 2025 Jul;81(7):3822-3832. doi: 10.1002/ps.8748. Epub 2025 Mar 13.
Plant diseases caused by plant viruses and pathogens seriously affect crop yield and quality, making prevention and control extremely difficult and posing a serious threat to human health. Marine alkaloids have novel structures and diverse biological activities, which are an important source of the development of new pesticides. In this work, ammosamide alkaloids were selected as the parent structure. A series of derivatives based on the chlorinated pyrrolo[4,3,2-de]quinoline were synthesized and evaluated for their antiviral and fungicidal activities.
Ammosamide B was efficiently synthesized from commercially available 6-chloroisatin in seven steps with an overall yield of 18.5%. A series of pyrrolo[4,3,2-de]quinoline derivatives were synthesized and evaluated for their antiviral and fungicidal activities. Most of these compounds were demonstrated to have higher antiviral activities than ribavirin. Particularly, compounds 7, 8a, 11, and 13a exhibited higher inhibitory activities against tobacco mosaic virus (TMV) and potato virus Y (PVY) than ningnanmycin. Antiviral mechanism research revealed that compound 13a can inhibit the assembly of TMV particles by interfering with the formation of the 20S coat protein (CP) disk. We further validated the interaction between this type of compound and TMV CP through molecular docking. This type of compounds also exhibits broad-spectrum inhibitory effects against eight common plant fungi, especially Physalospora piricola.
An improved method for synthesis of ammosamide B and its derivatives from commercially available 6-chloroisatin was explored. Systematic structural modifications based on ammosamide alkaloids were carried out and the structure-activity relationship of anti-TMV activity was summarized. Compound 13a, exhibiting excellent antiviral activity, has emerged as a new candidate for antiviral agents. The current work provides a valuable reference for exploring the potential applications of ammosamide derivatives in plant protection. © 2025 Society of Chemical Industry.
由植物病毒和病原体引起的植物病害严重影响作物产量和品质，防控极为困难，对人类健康构成严重威胁。海洋生物碱具有新颖的结构和多样的生物活性，是开发新型农药的重要来源。本研究选择氨莫酰胺生物碱作为母体结构，合成了一系列基于氯化吡咯并[4,3,2 - de]喹啉的衍生物，并对其抗病毒和杀菌活性进行了评价。
以市售的6 - 氯异吲哚酮为原料，经七步反应高效合成了氨莫酰胺B，总收率为18.5%。合成了一系列吡咯并[4,3,2 - de]喹啉衍生物，并对其抗病毒和杀菌活性进行了评价。这些化合物中的大多数表现出比利巴韦林更高的抗病毒活性。特别是，化合物7、8a、11和13a对烟草花叶病毒（TMV）和马铃薯Y病毒（PVY）的抑制活性高于宁南霉素。抗病毒机制研究表明，化合物13a可通过干扰20S外壳蛋白（CP）盘的形成来抑制TMV颗粒的组装。我们通过分子对接进一步验证了这类化合物与TMV CP之间的相互作用。这类化合物对八种常见植物真菌也表现出广谱抑制作用，尤其是对梨孢炭疽菌。
探索了一种以市售6 - 氯异吲哚酮为原料合成氨莫酰胺B及其衍生物的改进方法。基于氨莫酰胺生物碱进行了系统的结构修饰，总结了抗TMV活性的构效关系。具有优异抗病毒活性的化合物13a已成为抗病毒剂的新候选物。目前的工作为探索氨莫酰胺衍生物在植物保护中的潜在应用提供了有价值的参考。© 2025化学工业协会
