Cinnamic
acid, isolated from cinnamon bark, is a natural product
with excellent bioactivity, and it effectively binds with cyclohexanedione
to form novel 4-hydroxyphenylpyruvate dioxygenase (HPPD) inhibitors.
According to the active sub-structure combination principle, a series
of novel 3-hydroxy-2-cinnamoyl-2-en-1-one derivatives were designed
and synthesized. The title compounds were characterized by infrared, 1H NMR, 13C NMR, and HRMS. The in vitro inhibitory
activity of AtHPPD verified that compound II-13 showed
the most activity with a half-maximal inhibitory concentration (IC50) value of 0.180 μM, which was superior to that of
mesotrione (0.206 μM) in vitro. The preliminary herbicidal activity
tests demonstrated that some compounds had good herbicidal activity
especially compound II-13 at a concentration of 150 g ai/ha. The binding
mode of AtHPPD through molecular docking indicated
that two oxygens of compounds II-13 formed bidentate interactions
with metal ions, and the benzene ring formed π-π accumulation
effects with Phe-381 and Phe-424. The results of molecular dynamics
simulations showed that compound II-13 exhibited a more stable binding
ability with AtHPPD than mesotrione. This study provided
insights into the development of natural and efficient herbicides
in the future.
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