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首页> 外文期刊>Journal of Agricultural and Food Chemistry >Discovery of a Novel Series of Tricyclic Oxadiazine 4a-Methyl Esters Based on Indoxacarb as Potential Sodium Channel Blocker/Modulator Insecticides
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Discovery of a Novel Series of Tricyclic Oxadiazine 4a-Methyl Esters Based on Indoxacarb as Potential Sodium Channel Blocker/Modulator Insecticides

机译：发现基于吲哚氏菌的新型三环二嗪4A-甲酯系列作为潜在钠通道阻滞剂/调节剂杀虫剂

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Indoxacarb, a commercialized oxadiazine insecticide, nearly irreversibly blocks open/inactivated, but not resting sodium channels. The structure-activity relationships showed that the substituents at the position of the chiral atom in the oxadiazine ring are very important to the biological activity of oxadiazine insecticide. Here we synthesized a series of tricyclic oxadiazine 4a-methyl ester derivatives. The chiral atom in the oxadiazine ring has been epimerized and substituted with either pyrethric acid or cinnamic acid derivatives. Benzene ring in the tricyclic moiety was substituted with a chlorine, fluorine, or bromine atom, and nitrogen-linked benzene ring was substituted with a trifluoromethyl or trifluoromethoxy group. Toxicity of these compounds against Spodoptera litura F. was evaluated. Diastereoisomers of most toxic compounds J7 and J9 with pyrethric acid moiety were separated by flash column chromatography. The more polar diastereoisomers, J7-L-Rf and J9-L-Rf, and compounds J24 and J26 with cinnamic acid moiety exhibited highest insecticidal activities. We further used Monte Carlo energy minimizations to dock compound J7 and J24 in the NavMs-based homology model of the open cockroach sodium channel. In the low-energy binding modes, the compound interacted with residues in the inner pore and domain interfaces, which previously were proposed to contribute to receptors of pyrethroids and sodium channel blocker insecticides. Our results define compound J7 and J24 as a potentially useful optimized hit for the development of multiple sites sodium channel blocker or modulator.
机译：Indoxacarb，商业化的氧化氨酸杀虫剂，几乎不可逆转地阻塞开/灭活，但不静止钠通道。结构 - 活性关系表明，恶性原子在恶臭环中的取代基对恶毒苷杀虫剂的生物活性非常重要。在这里，我们合成了一系列三环氧基嗪4A-甲酯衍生物。恶毒嗪环中的手性原子已经被留下并被留脂酸或肉桂酸衍生物取代并取代。三环部分中的苯环被氯，氟或溴原子取代，并用三氟甲基或三氟甲氧基取代氮气苯环。评价这些化合物对Spodoptera Litura F的毒性。通过快速柱色谱法分离具有留下酸部分的大多数毒性化合物J7和J9的非对映异构体。具有肉桂酸部分的较大的极性非对映异构体，J7-L-RF和J9-L-RF和化合物J24和J26表现出最高的杀虫活性。我们进一步使用Monte Carlo能量最小化在开放的蟑螂钠通道的基于Navms的同源模型中停靠化合物J7和J24。在低能量结合模式中，将化合物与内孔中的残基相互作用，并提出了先前的域界面，这有助于拟除虫菊酯和钠通道阻滞剂杀虫剂的受体。我们的结果将化合物J7和J24定义为潜在有用的优化击球，用于多个位点钠通道阻滞剂或调制器。

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