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Synthesis, antifungal activity, and molecular simulation study of nootkatone‐based thiazole‐hydrazone compounds as novel succinate dehydrogenase inhibitor
Pest Management Science ( IF 3.8 ) Pub Date : 2025-01-22 , DOI: 10.1002/ps.8669
Maofang Yang, Guishan Lin, Wengui Duan, Fangyao Li, Yucheng Cui, Yin Man, Yuzhi Lu, Luqiong Meng
Pest Management Science ( IF 3.8 ) Pub Date : 2025-01-22 , DOI: 10.1002/ps.8669
Maofang Yang, Guishan Lin, Wengui Duan, Fangyao Li, Yucheng Cui, Yin Man, Yuzhi Lu, Luqiong Meng
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BACKGROUNDPlant diseases cause huge losses in agriculture worldwide every year, but the prolonged use of current commercial fungicides has led to the development of resistance in plant pathogenic fungi. Therefore, there is an urgent need to develop new, efficient, and green fungicides.RESULTSTwenty‐three nootkatone‐based thiazole‐hydrazone compounds were designed, synthesized, and characterized by Fourier‐transform infrared (FTIR), proton (1 H) nuclear magnetic resonance (NMR), carbon‐13 (13 C) NMR, and high‐resolution mass spectrometry (HRMS). The antifungal activities results showed that all the target compounds displayed certain antifungal activity against eight tested fungi. Among them, target compounds 3a (88.7%), 3b (92.5%), 3d (88.7%), 3f (84.9%), 3j (88.7%), and 3l (92.5%) were comparable or superior to the positive control boscalid (88.7%) in their inhibitory activities against Physalospora piricola . Meanwhile, target compound 3l had half maximal effective concentration (EC50 ) values of 18.0172, 18.8236, 16.5914, 18.5044, and 16.5660 μg/mL against Fusarium oxysporum f. sp. cucumerinum , Alternaria solani , Gibberella zeae , Bipolaris maydis , and Colleterichum orbicalare , respectively, exhibiting outstanding and broad‐spectrum fungicidal activity. Moreover, a three‐dimensional quantitative structure–activity relationship (3D‐QSAR) study was carried out to investigate the relationship between the molecular structures of target compounds 3a–3w and their antifungal activity. Furthermore, the target compound 3l [half maximal inhibitory concentration (IC50 ) = 4.936 μmol/L] showed significantly better inhibitory activity against succinate dehydrogenase (SDH) than boscalid (IC50 = 6.631 μmol/L). The possible binding mode between target compound 3l and homology‐modeling built SDH, was also explored by molecular docking.CONCLUSIONTarget compound 3l deserved further study as the promising candidate for the development of novel SDH inhibitor. © 2025 Society of Chemical Industry.
中文翻译:
基于 nootkatone 的噻唑腙化合物作为新型琥珀酸脱氢酶抑制剂的合成、抗真菌活性和分子模拟研究
背景疾病每年都会给全球农业造成巨大损失,但当前商业杀菌剂的长期使用导致植物病原真菌产生耐药性。因此,迫切需要开发新的、高效的、绿色的杀菌剂。结果设计、合成了 23 种基于 nootkatone 的噻唑腙化合物,并通过傅里叶变换红外 (FTIR)、质子 (1H) 核磁共振 (NMR)、碳 13 (13C) NMR 和高分辨率质谱 (HRMS) 进行了表征。抗真菌活性结果表明,所有目标化合物对 8 种供试真菌均表现出一定的抗真菌活性。其中,目标化合物 3a (88.7%) 、 3b (92.5%) 、 3d (88.7%) 、 3f (84.9%) 、 3j (88.7%) 和 3l (92.5%) 对梨孢菌的抑制活性与阳性对照啶酰菌 (88.7%) 相当或更优越。同时,目标化合物 3l 对尖孢镰刀菌、茄子孢菌、玉米赤霉菌、双极菌和炭疽菌的半数最大有效浓度 (EC50) 分别为 18.0172、18.8236、16.5914、18.5044 和 16.5660 μg/mL,表现出出色的广谱杀菌活性。此外,还进行了三维定量构效关系 (3D-QSAR) 研究,以研究目标化合物 3a-3w 的分子结构与其抗真菌活性之间的关系。此外,目标化合物 3l [半数最大抑菌浓度 (IC50) = 4.936 μmol/L] 对琥珀酸脱氢酶 (SDH) 的抑制活性显著优于啶酰菌胺 (IC50 = 6.631 μmol/L)。 还通过分子对接探索了靶化合物 3l 与同源建模构建的 SDH 之间可能的结合模式。结论化合物 3l 作为开发新型 SDH 抑制剂的有前途的候选者,值得进一步研究。© 2025 化工学会.
更新日期:2025-01-22
中文翻译:
![](https://scdn.x-mol.com/jcss/images/paperTranslation.png)
基于 nootkatone 的噻唑腙化合物作为新型琥珀酸脱氢酶抑制剂的合成、抗真菌活性和分子模拟研究
背景疾病每年都会给全球农业造成巨大损失,但当前商业杀菌剂的长期使用导致植物病原真菌产生耐药性。因此,迫切需要开发新的、高效的、绿色的杀菌剂。结果设计、合成了 23 种基于 nootkatone 的噻唑腙化合物,并通过傅里叶变换红外 (FTIR)、质子 (1H) 核磁共振 (NMR)、碳 13 (13C) NMR 和高分辨率质谱 (HRMS) 进行了表征。抗真菌活性结果表明,所有目标化合物对 8 种供试真菌均表现出一定的抗真菌活性。其中,目标化合物 3a (88.7%) 、 3b (92.5%) 、 3d (88.7%) 、 3f (84.9%) 、 3j (88.7%) 和 3l (92.5%) 对梨孢菌的抑制活性与阳性对照啶酰菌 (88.7%) 相当或更优越。同时,目标化合物 3l 对尖孢镰刀菌、茄子孢菌、玉米赤霉菌、双极菌和炭疽菌的半数最大有效浓度 (EC50) 分别为 18.0172、18.8236、16.5914、18.5044 和 16.5660 μg/mL,表现出出色的广谱杀菌活性。此外,还进行了三维定量构效关系 (3D-QSAR) 研究,以研究目标化合物 3a-3w 的分子结构与其抗真菌活性之间的关系。此外,目标化合物 3l [半数最大抑菌浓度 (IC50) = 4.936 μmol/L] 对琥珀酸脱氢酶 (SDH) 的抑制活性显著优于啶酰菌胺 (IC50 = 6.631 μmol/L)。 还通过分子对接探索了靶化合物 3l 与同源建模构建的 SDH 之间可能的结合模式。结论化合物 3l 作为开发新型 SDH 抑制剂的有前途的候选者,值得进一步研究。© 2025 化工学会.