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 Journal of Pesticide Science Pub Date : 2024-05-17 DOI:10.1584/jpestics.d24-004
Kotaro Mori, Masahiro Miyashita, Soichirou Mori, Norio Shibata, Yoshiaki Nakagawa
{"title":"Quantitative structure–activity relationship of 2,6-dimethoxy-N-(3-(4-substituted phenyl)isoxazol-5-yl)benzamide for the inhibition of chitin synthesis","authors":"Kotaro Mori, Masahiro Miyashita, Soichirou Mori, Norio Shibata, Yoshiaki Nakagawa","doi":"10.1584/jpestics.d24-004","DOIUrl":null,"url":null,"abstract":"</p><p>Previously, we found that 5-(2,6-dimethoxybenzoylamino)-3-phenylisoxazoles (IOXs) inhibit chitin synthesis in the cultured integument of <i>Chilo suppressalis</i>. In this study, IOXs with various substituents at the <i>para</i>-position of the 3-phenyl ring were synthesized, and the concentrations required to inhibit chitin synthesis to 50% (IC<sub>50</sub>) were determined for all compounds. The introduction of halogens—such as F, Cl, and Br—and small alkyls—such as Me, Et, Pr, and <i>n</i>-Bu—at the 3-phenyl ring slightly enhanced the activity. However, the activity decreased drastically with the introduction of NO<sub>2</sub>, CF<sub>3</sub>, and <i>t</i>-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 <i>E</i><sub><i>s</i></sub> was detrimental to the activity.</p>\n<p></p>\n<img alt=\"\" src=\"https://www.jstage.jst.go.jp/pub/jpestics/advpub/0/advpub_D24-004/figure/advpub_D24-004.png\"/>\n<span style=\"padding-left:5px;\">Fullsize Image</span>","PeriodicalId":16712,"journal":{"name":"Journal of Pesticide Science","volume":"33 1","pages":""},"PeriodicalIF":1.5000,"publicationDate":"2024-05-17","publicationTypes":"Journal Article","fieldsOfStudy":null,"isOpenAccess":false,"openAccessPdf":"","citationCount":"0","resultStr":null,"platform":"Semanticscholar","paperid":null,"PeriodicalName":"Journal of Pesticide Science","FirstCategoryId":"97","ListUrlMain":"https://doi.org/10.1584/jpestics.d24-004","RegionNum":4,"RegionCategory":"农林科学","ArticlePicture":[],"TitleCN":null,"AbstractTextCN":null,"PMCID":null,"EPubDate":"","PubModel":"","JCR":"Q2","JCRName":"ENTOMOLOGY","Score":null,"Total":0}
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
查看原文
分享 分享
微信好友 朋友圈 QQ好友 复制链接
本刊更多论文
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。
本文章由计算机程序翻译,如有差异,请以英文原文为准。
求助全文
约1分钟内获得全文 去求助
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.
期刊最新文献
Effect of pyriofenone on the infection processes and cytological features of Blumeria graminis on wheat leaves Synthesis and biological evaluation of burnettiene A derivatives enabling discovery of novel fungicide candidates. Enhanced disease resistance against Botrytis cinerea by strigolactone-mediated immune priming in Arabidopsis thaliana A reliable quantification of organophosphorus pesticides in brown rice samples for proficiency testing using Japanese official analytical method, QuEChERS, and modified QuEChERS combined with isotope dilution mass spectrometry Bacterial Pesticides: Mechanism of Action, Possibility of Food Contamination, and Residue Analysis Using MS
×
引用
GB/T 7714-2015
复制
MLA
复制
APA
复制
导出至
BibTeX EndNote RefMan NoteFirst NoteExpress
×
×
提示
您的信息不完整,为了账户安全,请先补充。
现在去补充
×
提示
您因"违规操作"
具体请查看互助需知
我知道了
×
提示
现在去查看 取消
×
提示
确定
0
微信
客服QQ
Book学术公众号 扫码关注我们
反馈
×
意见反馈
请填写您的意见或建议
请填写您的手机或邮箱
已复制链接
已复制链接
快去分享给好友吧!
我知道了
×
扫码分享
扫码分享
Book学术官方微信
Book学术文献互助
Book学术文献互助群
群 号:481959085
Book学术
文献互助 智能选刊 最新文献 互助须知 联系我们:info@booksci.cn
Book学术提供免费学术资源搜索服务,方便国内外学者检索中英文文献。致力于提供最便捷和优质的服务体验。
Copyright © 2023 Book学术 All rights reserved.
ghs 京公网安备 11010802042870号 京ICP备2023020795号-1