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Design, Synthesis, and Bioactivity of Spiro Derivatives Containing a Pyridine Moiety.

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We designed and synthesized a series of pyridine spiro derivatives and evaluated their insecticidal and antiviral activities. Some compounds exhibited good insecticidal and antiviral activities. Notably, the E series of… Click to show full abstract

We designed and synthesized a series of pyridine spiro derivatives and evaluated their insecticidal and antiviral activities. Some compounds exhibited good insecticidal and antiviral activities. Notably, the E series of compounds displayed good insecticidal activity against Tetranychus urticae. Compounds E20 (EC50 = 63.68 mg/L) and F4 (EC50 = 47.81 mg/L) exhibited inactivation activities against the tobacco mosaic virus (TMV), which were similar to that of Ningnanmycin (EC50 = 58.01 mg/L). Molecular docking showed that compounds E20 and F4 exhibited satisfactory affinities for the TMV coat protein (TMV-CP), with binding energies (-6.7 and -6.4 kcal/mol, respectively) slightly lower than that of Ningnanmycin (-6.3 kcal/mol). Further, molecular dynamics analysis revealed that compounds E20 and F4 exhibited better binding stability values than Ningnanmycin. Microscale thermophoresis showed that compounds E20 (Kd = 0.053 ± 0.016 μM) and F4 (Kd = 0.045 ± 0.022 μM) bound more strongly to TMV-CP than Ningnanmycin (Kd = 0.10 ± 0.029 μM). The results of transmission electron microscopy showed that these two compounds hindered the self-assembly and growth of TMV. In summary, we showed that these pyridine spiro derivatives could be used as a basis for the research and development of novel pesticides.

Keywords: compounds e20; design synthesis; bioactivity spiro; spiro derivatives; pyridine; synthesis bioactivity

Journal Title: Journal of agricultural and food chemistry
Year Published: 2022

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