Quantitative structure–activity relationship of 2,6-dimethoxy-N-(3-(4-substituted phenyl)isoxazol-5-yl)benzamide for the inhibition of chitin synthesis

IF 1.5 4区 农林科学 Q2 ENTOMOLOGY
Kotaro Mori, Masahiro Miyashita, Soichirou Mori, Norio Shibata, Yoshiaki Nakagawa
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引用次数: 0

Abstract

Previously, we found that 5-(2,6-dimethoxybenzoylamino)-3-phenylisoxazoles (IOXs) inhibit chitin synthesis in the cultured integument of Chilo suppressalis. In this study, IOXs with various substituents at the para-position of the 3-phenyl ring were synthesized, and the concentrations required to inhibit chitin synthesis to 50% (IC50) were determined for all compounds. The introduction of halogens—such as F, Cl, and Br—and small alkyls—such as Me, Et, Pr, and n-Bu—at the 3-phenyl ring slightly enhanced the activity. However, the activity decreased drastically with the introduction of NO2, CF3, and t-Bu. The quantitative analysis of the substituent effect at the 3-phenyl ring on chitin-synthesis inhibition using the Hansch-Fujita method showed that the hydrophobic substituent with the optimum value was favored for the activity, but the bulky substituent in terms of Es was detrimental to the activity.

Abstract Image Fullsize Image
抑制甲壳素合成的 2,6-二甲氧基-N-(3-(4-取代苯基)异恶唑-5-基)苯甲酰胺的定量结构-活性关系
此前,我们发现 5-(2,6-二甲氧基苯甲酰氨基)-3-苯基异噁唑(IOXs)可抑制抑虱培养体中几丁质的合成。本研究合成了在 3-苯基环的对位上具有不同取代基的 IOXs,并测定了所有化合物抑制几丁质合成至 50%所需的浓度(IC50)。在 3-苯基环上引入卤素(如 F、Cl 和 Br)和小烷基(如 Me、Et、Pr 和 n-Bu)会略微提高活性。然而,引入 NO2、CF3 和 t-Bu 后,活性急剧下降。利用 Hansch-Fujita 方法定量分析了 3-苯基环上的取代基对甲壳素合成抑制作用的影响,结果表明,具有最佳值的疏水取代基有利于活性的提高,而以 Es 计的笨重取代基则不利于活性的提高。
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来源期刊
Journal of Pesticide Science
Journal of Pesticide Science 农林科学-昆虫学
CiteScore
4.30
自引率
4.20%
发文量
28
审稿时长
18-36 weeks
期刊介绍: The Journal of Pesticide Science publishes the results of original research regarding the chemistry and biochemistry of pesticides including bio-based materials. It also covers their metabolism, toxicology, environmental fate and formulation.
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