Synthesis, Biological Activity and 3D-QSAR Study of Novel Pyrrolidine-2,4-dione Derivatives Containing N-Substituted Phenylhydrazine Moiety

doi:10.1007/s40242-015-4348-3

Chemical Research in Chinese Universities ›› 2015, Vol. 31 ›› Issue (2): 228-234.doi: 10.1007/s40242-015-4348-3

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Synthesis, Biological Activity and 3D-QSAR Study of Novel Pyrrolidine-2,4-dione Derivatives Containing N-Substituted Phenylhydrazine Moiety

ZHANG Lizhi^1,3, REN Zhengjiao^1,3, LU Aimin^2,3, ZHAO Zheng^2,3, XU Wenqin^1,3, BAO Qianqian³, DING Weijie³, YANG Chunlong^1,2,3

1. Jiangsu Key Laboratory of Pesticide Science, Nanjing Agricultural University, Nanjing 210095, P. R. China;
2. Key Laboratory of Monitoring and Management of Crop Diseases and Pest Insects, Ministry of Agriculture, Nanjing Agricultural University, Nanjing 210095, P. R. China;
3. College of Science, Nanjing Agricultural University, Nanjing 210095, P. R. China

Received:2014-09-19 Revised:2014-10-20 Online:2015-04-01 Published:2014-11-17
Contact: YANG Chunlong E-mail:ycl@njau.edu.cn
Supported by:
Supported by the National High Technology Research and Development Program of China(No.2011AA10A206), the National Key Technologies R&D Program of China(No.2011BAE06B04), the Science & Technology Pillar Program of Jiangsu Province, China(No.BE2012371), the National Natural Science Foundation of China(No.31171889) and the Fundamental Research Funds for the Central Universities of China(No.KYZ201223).

Abstract

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 q² value of 0.585 and Noncross-validated correlation coefficient r² 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.

Key words: Pyrrolidine-2,4-dione, N-Substituted phenylhydrazine, Antifungal activity, 3D quantitative structure acti-vity relationship(3D-QSAR)

ZHANG Lizhi, REN Zhengjiao, LU Aimin, ZHAO Zheng, XU Wenqin, BAO Qianqian, DING Weijie, YANG Chunlong. Synthesis, Biological Activity and 3D-QSAR Study of Novel Pyrrolidine-2,4-dione Derivatives Containing N-Substituted Phenylhydrazine Moiety[J]. Chemical Research in Chinese Universities, 2015, 31(2): 228-234.

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Synthesis, Biological Activity and 3D-QSAR Study of Novel Pyrrolidine-2,4-dione Derivatives Containing N-Substituted Phenylhydrazine Moiety

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