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Discovery of 3-Formyl-N-(un)Substituted Benzylindole Pyrimidines as an Acaricidal Agent and Their Mechanism of Action
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-11-01 , DOI: 10.1021/acs.jafc.3c06409 Tianze Li 1 , Min Lv 1 , Houpeng Wen 1 , Hui Xu 1
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2023-11-01 , DOI: 10.1021/acs.jafc.3c06409 Tianze Li 1 , Min Lv 1 , Houpeng Wen 1 , Hui Xu 1
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To discover the pronounced acaricide candidate, herein, a series of 3-formyl-N-(un)substituted benzylindole pyrimidines were prepared by structural modification of indoles at the N-1 and C-3 positions via the successive Vilsmeier–Haack–Arnold (VHA), aldol condensation, and cyclization reactions. The steric structures of nine compounds were undoubtedly confirmed by X-ray single-crystallography. Against Tetranychus cinnabarinus Boisduval, compounds V-15, V-31, V-34, V-42, V-44, and V-60 exhibited promising acaricidal activity with LC50 values of 0.299–0.481 mg/mL. In particular, compound V-34 displayed 4.2 times the acaricidal activity of its precursor 6-methylindole. Scanning electron microscopy (SEM) imaging revealed that the construction of the cuticle layer of V-34-treated T. cinnabarinus was seriously destroyed. Furthermore, RNA-Seq analysis indicated that compound V-34 could regulate the homeostasis metabolism of T. cinnabarinus through arachidonic acid and linoleic acid metabolism and lysosome pathways. These results suggested that compound V-34 can be further studied as a lead acaricidal agent.
中文翻译：
3-甲酰基-N-(未)取代的苯甲基吲哚嘧啶作为杀螨剂的发现及其作用机制
为了发现明显的杀螨剂候选物，本文通过连续的 Vilsmeier-Haack-Arnold ( VHA)、羟醛缩合和环化反应。9种化合物的空间结构无疑已通过X射线单晶分析得到证实。针对朱砂叶螨，化合物V-15、V-31、V-34、V-42、V-44和V-60表现出良好的杀螨活性，LC 50值为 0.299 – 0.481 mg/mL。特别是，化合物V-34的杀螨活性是其前体6-甲基吲哚的4.2倍。扫描电子显微镜（SEM）成像显示，经V-34处理的朱砂毛鳞片的角质层结构被严重破坏。此外，RNA-Seq分析表明，化合物V-34可以通过花生四烯酸和亚油酸代谢以及溶酶体途径调节朱砂的稳态代谢。这些结果表明化合物V-34可以作为先导杀螨剂进行进一步研究。
更新日期：2023-11-01
中文翻译：
3-甲酰基-N-(未)取代的苯甲基吲哚嘧啶作为杀螨剂的发现及其作用机制
为了发现明显的杀螨剂候选物，本文通过连续的 Vilsmeier-Haack-Arnold ( VHA)、羟醛缩合和环化反应。9种化合物的空间结构无疑已通过X射线单晶分析得到证实。针对朱砂叶螨，化合物V-15、V-31、V-34、V-42、V-44和V-60表现出良好的杀螨活性，LC 50值为 0.299 – 0.481 mg/mL。特别是，化合物V-34的杀螨活性是其前体6-甲基吲哚的4.2倍。扫描电子显微镜（SEM）成像显示，经V-34处理的朱砂毛鳞片的角质层结构被严重破坏。此外，RNA-Seq分析表明，化合物V-34可以通过花生四烯酸和亚油酸代谢以及溶酶体途径调节朱砂的稳态代谢。这些结果表明化合物V-34可以作为先导杀螨剂进行进一步研究。
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