高等学校化学学报 ›› 2004, Vol. 25 ›› Issue (1): 71.

• 研究论文 • 上一篇    下一篇

新型黄烷酮类衍生物的合成、杀菌活性及定量构效关系研究

杨光富1, 丁宇2, 杨华铮2, 吴小军3   

  1. 1. 华中师范大学化学学院, 武汉 430079;
    2. 南开大学元素有机化学国家重点实验室, 天津 300071;
    3. 武汉大学化学与分子科学学院, 武汉 430075
  • 收稿日期:2002-11-04 出版日期:2004-01-24 发布日期:2004-01-24
  • 通讯作者: 杨光富(1970年出生),男,博士,教授,博士生导师,从事农药化学研究.E-mail:gfyang@ccnu.edu.cn E-mail:gfyang@ccnu.edu.cn
  • 基金资助:

    国家自然科学基金(批准号:20172017,29802002);国家重大基础研究前期专项基金(批准号:2002CCA00500);教育部跨世纪优秀人才培养计划和教育部骨干教师资助计划(批准号:GG-150-10511-1005)资助

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

YANG Guang-Fu1, DING Yu2, YANG Hua-Zheng2, WU Xiao-Jun3   

  1. 1. College of Chemistry, Central China Normal University, Wuhan 430079, China;
    2. National Key Laboratory of Elemento-Organic Chemistry, Nankai University, Tianjin 300071, China;
    3. College of Chemistry and Molecular Science, Wuhan University, Wuhan 430075, China
  • Received:2002-11-04 Online:2004-01-24 Published:2004-01-24

摘要: 设计合成了14个含不同性质取代基的黄烷酮类化合物,并采用核磁共振氢波谱、质谱和元素分析对所有化合物的结构进行了表征.在系统测定化合物对水稻稻瘟病抑制活性的IC50值的基础上,采用Hansch-Fujita方法和CoMFA方法对其定量结构活性关系进行了系统研究,结果发现,化合物的疏水性质、极化效应以及最高空轨道能级对杀菌活性有重要影响,化合物的疏水参数越小,分子越容易极化,则化合物的杀菌活性越高.此外,最高空轨道能级越低,化合物越容易接受电子,其杀菌活性也相应提高.通过考察∑π、clgP以及lgK与化合物杀菌活性的相关性,发现lgK能较好地反映该类化合物的疏水效应.三维定量构效关系研究表明,B环2,3,4位上含有较大体积的取代基,而6位含较小体积的取代基,有利于提高其杀菌活性.

关键词: 植物抗毒素, 黄烷酮, 杀菌活性, 定量构效关系, CoMFA

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

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