Synthesis and Evaluation of Halogenated 5-(2-Hydroxyphenyl)pyrazoles as Pseudilin Analogues Targeting the Enzyme IspD in the Methylerythritol Phosphate Pathway.,Journal of Agricultural and Food Chemistry

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Synthesis and Evaluation of Halogenated 5-(2-Hydroxyphenyl)pyrazoles as Pseudilin Analogues Targeting the Enzyme IspD in the Methylerythritol Phosphate Pathway.
Journal of Agricultural and Food Chemistry ( IF 5.7 ) Pub Date : 2020-02-20 , DOI: 10.1021/acs.jafc.9b08057
Jili Wang ₁ , Yaqing Zhou ₁ , Xiuwen Wang ₁ , Lixia Duan ₁ , Jiang Duan ₁ , Weiguo Li ₁ , Aidong Zhang ₁

Affiliation

This work reports halogenated 5-(2-hydroxyphenyl)pyrazoles as pseudilin analogues with the potential to target the enzyme IspD in the methylerythritol phosphate (MEP) pathway. Such analogues were designed using the bioisosteric replacement of the pseudilin core structure and synthesized via an efficient three-step route. With AtIspD-based screening and pre- and post-emergence herbicidal tests, these compounds were demonstrated to have considerable activities against AtIspD, with IC50 up to 3.27 μM, and against model plants rape and barnyard grass, with moderate to excellent activities. At a rate of 150 g/ha in the greenhouse test, three compounds exhibited higher or comparable herbicidal activities than pseudilin. Molecular docking of representative compounds into the allosteric site of AtIspD revealed a binding mode similar to that of pseudilin. The established bioisosterism and synthesis method in this work may serve as an important tool for the development of new herbicides and antimicrobials targeting IspD in the MEP pathway.

中文翻译：

卤代5-（2-羟苯基）吡唑类化合物的合成和评价，作为Pseudilin类似物，靶向甲基赤藓糖醇磷酸途径中的酶IspD。

这项工作报告了卤代5-（2-羟苯基）吡唑类作为假性泛素类似物，具有靶向磷酸甲基赤藓糖醇（MEP）途径中的酶IspD的潜力。此类类似物是利用伪seedlin核心结构的生物立体置换来设计的，并通过有效的三步法合成。通过基于AtIspD的筛选以及芽前和芽后除草测试，这些化合物被证明具有抗AtIspD（IC50高达3.27μM）和模型植物油菜和n草的相当大的活性，活性中等至优异。在温室试验中，以150 g / ha的速率，三种化合物的除草活性高于假单胞菌素。代表性化合物的分子对接至AtIspD的变构位点揭示了一种类似于假性尿素的结合模式。

更新日期：2020-03-02

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