Department of Chemistry, Punjab Agricultural University, Ludhiana, Punjab, India.
Department of Plant Pathology, Punjab Agricultural University, Ludhiana, Punjab, India.
J Environ Sci Health B. 2022;57(8):657-669. doi: 10.1080/03601234.2022.2097504. Epub 2022 Aug 5.
Regioselective nucleophilic addition of unsubstituted isatin () was carried out for the synthesis of pharmaceutically and to be agrochemically important 3-hydroxy-3-akylindolin-2-ones () using discrete nucleophiles generation of Grignard reagent. The synthesized derivatives were characterized by spectral techniques and were evaluated for nematicidal activity against . The nematicidal assay revealed that 1-ethyl-3-hydroxyindolin-2-one () exhibited potent nematicidal activity against . The most active member ( exhibited reasonably good ovicidal (LC = 0.077 mg/mL) and larvicidal activity (LC = 0.058 mg/mL), respectively. In support of the nematicidal activity, molecular docking of isatin (1) and its derivatives ( was performed using three parasitic proteins ., carboxylic ester hydrolase, cytochrome c oxidase and aspartyl protease which revealed maximum interaction with amino acid residues Tyr 356, Tyr 170, Glu 238, Glu 327, Arg 271, Arg 112, Ser 29, Ser 31, Ser 368, Asn 115, Leu 326 and His 51 which act as supporting factors for compounds to curb the parasite.
采用离散的亲核试剂 Grignard 试剂，对未取代的靛红（）进行区域选择性亲核加成反应，合成了具有重要药用和农用价值的 3-羟基-3-取代基吲哚啉-2-酮（）。所合成的衍生物通过光谱技术进行了表征，并对其进行了针对 的杀线虫活性评估。杀线虫活性测定表明，1-乙基-3-羟基吲哚啉-2-酮（）对 表现出很强的杀线虫活性。最活跃的成员（）表现出良好的杀卵活性（LC = 0.077 mg/mL）和幼虫活性（LC = 0.058 mg/mL）。为了支持杀线虫活性，采用三种寄生蛋白对靛红（1）及其衍生物（进行了分子对接。羧酸酯水解酶、细胞色素 c 氧化酶和天冬氨酸蛋白酶，结果表明与 Tyr 356、Tyr 170、Glu 238、Glu 327、Arg 271、Arg 112、Ser 29、Ser 31、Ser 368、Asn 115、Leu 326 和 His 51 等氨基酸残基的相互作用最大，这些氨基酸残基作为支持因子，有助于化合物抑制寄生虫。
