Design, synthesis, antibacterial and insecticidal activities of novel N-phenylpyrazole fraxinellone hybrid compounds
Design, synthesis, antibacterial and insecticidal activities of novel N-phenylpyrazole fraxinellone hybrid compounds
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新型N-苯基吡唑fraxinellone杂化化合物的设计、合成及其抗菌和杀虫活性
DOI：
10.1039/c6ra28064a
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发表时间：
2017-01-01
期刊：
影响因子：
3.9
通讯作者：
Zhang, Yanbing
中科院分区：
文献类型：
--
作者：
Guo, Yong;Wang, Xiaoguang;Zhang, Yanbing
在继续我们的研究，旨在发现和开发的天然产物为基础的抗菌剂和杀虫剂，一系列的20个新的N-苯基吡唑fraxinellone杂合化合物的制备和评价其抗菌和杀虫活性。化合物4 h和4 r的两个关键空间构型通过X射线晶体学明确确定。虽然只有化合物4g显示出比杀虫活性更好的对枯草芽孢杆菌的抗菌活性（MIC值为4 μ g mL（-1）），但化合物4 n、4 o和4 t显示出更有希望的杀虫活性，当与它们的前体秦皮酮和阳性对照川楝素相比时，最终死亡率（FMR）> 60%。这表明在秦皮酮的C-4和C-5位引入多卤代苯基吡唑，尤其是引入N-（2-氯-4-氟苯基）吡唑，比单卤代苯基吡唑更有前途。
In continuation of our research aimed at the discovery and development of natural product-based antimicrobial and insecticidal agents, a series of 20 novel N-phenylpyrazole fraxinellone hybrid compounds were prepared and evaluated for their antibacterial and insecticidal activities. Two key steric configurations of compounds 4h and 4r were unambiguously determined by X-ray crystallography. Although only compound 4g showed better antibacterial activity against Bacillus subtilis with MIC value of 4 mu g mL(-1), than insecticidal activity, compounds 4n, 4o and 4t exhibited more promising insecticidal activity with final mortality rates ( FMRs) of > 60%, when compared with their precursor fraxinellone and the positive control toosendanin. This suggested that introducing polyhalogenated phenylpyrazole at C-4 and C-5 positions of fraxinellone could lead to more promising insecticidal derivatives than monohalogenated phenylpyrazole, especially introducing N-(2-chloro-4-fluoro-phenyl)pyrazole.