| Autor: |
Alves Bezerra Morais P; Programa de Pós-Graduação em Agroquímica, Universidade Federal do Espírito Santo, 29500000Alegre, ES, Brazil., Britto KB; Programa de Pós-Graduação em Ciências Farmacêuticas, Universidade Federal do Espírito Santo, 29075910Vitória, ES, Brazil., Messias E; Programa de Pós-Graduação em Agroquímica, Universidade Federal do Espírito Santo, 29500000Alegre, ES, Brazil., de Andrade P; Manchester Institute of Biotechnology, University of Manchester, 131 Princess Street, ManchesterM1 7DN, U.K., Werner E; Programa de Pós-Graduação em Biologia Vegetal, Universidade Federal do Espírito Santo, 29075-910Vitória, ES, Brazil., Costa AV; Programa de Pós-Graduação em Agroquímica, Universidade Federal do Espírito Santo, 29500000Alegre, ES, Brazil., Lacerda V Jr; Programa de Pós-Graduação em Química, Universidade Federal do Espírito Santo, 29075910Vitória, ES, Brazil., Pinheiro CJG; Centro de Ciências Agrárias e Engenharias, Universidade Federal do Espírito Santo, 29500-000Alegre, ES., de Paula H; Centro de Ciências Exatas, Naturais e da Saúde, Universidade Federal do Espírito Santo, 29500000Alegre, ES, Brazil., Borges WS; Programa de Pós-Graduação em Química, Universidade Federal do Espírito Santo, 29075910Vitória, ES, Brazil. |
| Abstrakt: |
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 p k i values of predicted inhibitory activity and contour maps revealing sterically bulky groups for 11 , the CF 3 group in ortho, and for 17 , Br in ortho, favoring the inhibitory ALS activity. |
