Synthesis, Fugicidal Activity and Quantitative Structure-activity Relationships of Novel Flavanone Derivatives

Abstract

Abstract: Fourteen novel flavanone derivatives containing various substituents were designed and synthesized, whose structures were confirmed by ¹H NMR, MS and elemental analysis. The fungicidal IC₅₀ in vitro against rice blast disease of the title compounds were tested and the quantitative relationship between their structures and fungicidal activities was analyzed by using comparative molecular field analysis(CoMFA) and Hansch-Fujita approach. The results show that the hydrophobicity, polarity effect and the energy of the highest unoccupied orbital are very important for fungicidal activity. If the molecule was easy to polarize and had a lower LUMO energy, it would show a high fungicidal activity. Correlation results show that lgK is the most suitable parameter to describe the hydrophobicity of the title compounds compared to two other hydrophobic parameters, Σπand clgP. The results of 3D-QSAR analysis suggests that the introduction of steric bulk group onto the 2,3,4-position and small steric bulk onto the 6-position of B ring will be favorable to the activity of the compound. The CoMFA analyses about the electronic property requirement are consistent with those derived from the Hansch-Fujita approach.

Key words: Phytoalexins, Flavanones, Fungicidal activity, QSAR, CoMFA

CLC Number:

O621

TrendMD:

YANG Guang-Fu, DING Yu, YANG Hua-Zheng, WU Xiao-Jun . Synthesis, Fugicidal Activity and Quantitative Structure-activity Relationships of Novel Flavanone Derivatives[J]. Chem. J. Chinese Universities, 2004, 25(1): 71.

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Synthesis, Fugicidal Activity and Quantitative Structure-activity Relationships of Novel Flavanone Derivatives

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