Rational Design, Synthesis and Evaluation of Indole Nitrogen Hybrids as Photosystem II Inhibitors,Photochemistry and Photobiology

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Rational Design, Synthesis and Evaluation of Indole Nitrogen Hybrids as Photosystem II Inhibitors
Photochemistry and Photobiology ( IF 2.6 ) Pub Date : 2020-07-02 , DOI: 10.1111/php.13295
Jéssica Maria de Souza ₁ , Bruno Rodrigues Fazolo ₁ , Jhully Wellen Ferreira Lacerda ₁ , Mariana de Souza Moura ₁ , Arielly Celestino Rodrigues Dos Santos ₁ , Leonardo Gomes de Vasconcelos ₁ , Paulo Teixeira de Sousa Junior ₁ , Evandro Luiz Dall'Oglio ₁ , Akbar Ali ₂ , Olívia Moreira Sampaio ₁ , Lucas Campos Curcino Vieira ₃

Affiliation

We report the synthesis of twelve indole derivatives bearing nitro or amide groups via Fischer indole methodology followed by reduction/acetylation and amidation reactions. After thorough characterization, these indoles were subjected to a number of studies in order to evaluate their bioactive potential as photosynthesis and plant growth inhibitors. Firstly, these molecular hybrids were evaluated as photosystem II (PSII) inhibitors through chlorophyll a (Chl a) fluorescence measurement. In this study, 6‐chloro‐8‐nitro‐2,3,4,9‐tetrahydro‐1H‐carbazole (15a) and 5‐chloro‐2,3‐dimethyl‐7‐nitro‐1H‐indole (15b) showed the best results by reducing the phenomenological parameters of reaction centers ABS/RC, TR0/RC and ET0/RC of PSII. Electron chain blockage by these compounds may lead to diminished ATP synthesis and CO2 fixation which interrupt the plant development. The compounds 15a and 15b both act as postemergent herbicides, reducing the dry biomass of Ipomoea grandifolia and Senna alata weeds by an average of 40% and 37%, respectively, corroborating the fluorescence results. Additionally, the molecular docking study revealed that the presence of strong electron‐withdrawing groups at the indole phenyl ring is important for the ligand’s interaction with the binding pocket of protein D1 on PSII. The optimization of these molecular features is the goal of our research group in further understanding and development of new potent herbicides.

中文翻译：

吲哚氮杂化物作为光系统 II 抑制剂的合理设计、合成和评价

我们报告了通过 Fischer 吲哚方法合成十二个带有硝基或酰胺基团的吲哚衍生物，然后进行还原/乙酰化和酰胺化反应。在彻底表征之后，对这些吲哚进行了大量研究，以评估它们作为光合作用和植物生长抑制剂的生物活性潜力。首先，通过叶绿素 a (Chl a) 荧光测量将这些分子杂交体评估为光系统 II (PSII) 抑制剂。在这项研究中，6-氯-8-硝基-2,3,4,9-四氢-1H-咔唑（15a）和5-氯-2,3-二甲基-7-硝基-1H-吲哚（15b）表现出通过降低 PSII 的反应中心 ABS/RC、TR0/RC 和 ET0/RC 的现象学参数获得最佳结果。这些化合物的电子链阻塞可能导致 ATP 合成减少和 CO2 固定减少，从而中断植物发育。化合物 15a 和 15b 均用作芽后除草剂，分别将番薯和番泻叶杂草的干生物量平均减少 40% 和 37%，证实了荧光结果。此外，分子对接研究表明，吲哚苯环上存在强吸电子基团对于配体与 PSII 上蛋白质 D1 的结合口袋的相互作用很重要。这些分子特征的优化是我们研究小组进一步了解和开发新型强效除草剂的目标。将 Ipomoea grandifolia 和 Senna alata 杂草的干生物量分别平均减少 40% 和 37%，证实了荧光结果。此外，分子对接研究表明，吲哚苯环上存在强吸电子基团对于配体与 PSII 上蛋白质 D1 的结合口袋的相互作用很重要。这些分子特征的优化是我们研究组进一步了解和开发新型强效除草剂的目标。将 Ipomoea grandifolia 和 Senna alata 杂草的干生物量分别平均减少 40% 和 37%，证实了荧光结果。此外，分子对接研究表明，吲哚苯环上存在强吸电子基团对于配体与 PSII 上蛋白质 D1 的结合口袋的相互作用很重要。这些分子特征的优化是我们研究小组进一步了解和开发新型强效除草剂的目标。

更新日期：2020-07-02

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