Synthesis and Phytotoxic Evaluation of Isatin Derivatives Supported by 3D-QSAR Study.

Journal of agricultural and food chemistry 2023 Jan 11

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Concerned about weed infestation, a major threat to food production and herbicide resistance that interferes in the mechanism of action of the main herbicides, we have synthesized eight isatin derivatives using the "Click Chemistry" approach through copper-catalyzed azide-alkyne cycloadditions (CuAAC). Sixteen isatin derivatives were evaluated for their phytotoxic activity against the seed culture of the model plants, Lactuca sativa and Allium cepa. Six of them showed phytotoxic activity similar to the positive control, trifluralin. Hypocotyl length measurement analysis in L. sativa revealed that triazole derivative 8 is more active than trifluralin. For A. cepa, root length measurement analyses revealed that 3, 10, 14, 16, and 17 were similar to the positive control trifluralin. Three-dimensional quantitative structure-activity relationship (3D-QSAR) comparative molecular field analysis (CoMFA) model construction using the acetolactate synthase (ALS) crystallographic structure displayed pki values of predicted inhibitory activity and contour maps revealing sterically bulky groups for 11, the CF3 group in ortho, and for 17, Br in ortho, favoring the inhibitory ALS activity.

Citation

Pedro Alves Bezerra Morais, Karolinni B Britto, Evandro Messias, Peterson de Andrade, Elias Werner, Adilson Vidal Costa, Valdemar Lacerda, Christiano Jorge Gomes Pinheiro, Heberth de Paula, Warley de Souza Borges. Synthesis and Phytotoxic Evaluation of Isatin Derivatives Supported by 3D-QSAR Study. Journal of agricultural and food chemistry. 2023 Jan 11;71(1):255-266