Synthesis, biological activities and structure-activity relationships for new avermectin analogues

文献类型： 外文期刊

第一作者： Zhang, Jian

作者： Zhang, Jian;Nan, Xiang;Cheng, Pi-Le;Zhang, Yan;Liu, Ying-Qian;Liu, Huanxiang;Zhang, Shao-Yong;Chen, An-Liang;Yu, Hai-Tao;Hu, Guan-Fang

作者机构：

关键词： Avermectin;Structural modifications;Insecticidal activities;QSAR analysis

期刊名称：EUROPEAN JOURNAL OF MEDICINAL CHEMISTRY （ 影响因子：6.514； 五年影响因子：6.099 ）

ISSN：

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收录情况： SCI

摘要： In an effort to discover new molecules with good insecticidal activities, more than 40 new avermectin derivatives were synthesized and evaluated for their biological activities against three species of arachnids, insects and nematodes, namely, Tetranychus Cinnabarinus, Aphis craccivora and Bursaphelenchus xylophilus. All the tested compounds showed potent inhibitory activities against three insect species. Notably, the majority of compounds exhibited high selectivity against T. cinnabarinus, some of which were much better in comparison with avermectin. Especially compounds 9j (LC50: 0.005 mu M) and 16d (LC50: 0.002 mu M) were 2.5- and 4.7-fold more active than avermectin (LC50: 0.013 mu M), respectively, against T cinnabarinus. Moreover, compounds 9b, 9d-f, 9h, 9j, 9I, 9n, 9p, 9r, 9v and 17d showed superior activities with LC50 values of 2.959-5.013 mu M compared to that of 1 (LC50: 6.746 mu M) against B. xylophilus. Meanwhile, the insecticidal activities of compounds 9f, 9g, 9h, and 9m against A. craccivora were 7-8 times better than that of avermectin, with LC50 values of 7.744, 5.634, 6.809, 7.939 and 52.234 mu M, respectively. Furthermore, QSAR analysis showed that the molecular shape, size, connectivity degree and electronic distribution of avermectin analogues had substantial effects on insecticidal potency. These preliminary results provided useful insight in guiding further modifications of avermectin in the development of potential new insecticides. (C) 2016 Elsevier Masson SAS. All rights reserved.

分类号： R9

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