Synthesis, biological activity and 3D-QSAR study of novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety

Abstract

Twenty-seven novel pyrrolidine-2,4-dione derivatives containing N-substituted phenylhydrazine moiety were synthesized. Their structures were confirmed by ¹H NMR, ¹³C NMR and MS. The half effective concentration (EC₅₀) values of the title compounds against the phytopathogenic fungi Rhizoctonia cerealis were evaluated. Compounds 6l and 6q displayed good bioactivity with EC₅₀ values of 1.626 and 2.043 μg/mL, respectively. The 3D quantitative structure activity relationship(3D-QSAR) model of CoMFA was established with reliable cross-validated correlation coefficient q ² value of 0.585 and Noncross-validated correlation coefficient r ² value of 0.971. This model provided a tool for guiding further design and synthesis of novel pyrrolidine-2,4-dione derivatives with high fungicidal activity.

Keywords

Pyrrolidine-2,4-dione / N-Substituted phenylhydrazine / Antifungal activity / 3D quantitative structure activity relationship(3D-QSAR)

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