含杂环1,4-戊二烯-3-酮肟酯类化合物的合成及生物活性

为创制具有较高生物活性的绿色农药,以姜黄素为先导,将具有良好生物活性的肟酯基团引入1,4-戊二烯-3-酮的骨架中,设计合成了一系列含杂环1,4-戊二烯-3-酮肟酯类化合物,其结构经红外光谱、核磁共振氢谱及碳谱和高分辨质谱确认。初步的生物活性测试结果表明,在药剂浓度为50mg/L时,化合物5d对小麦赤霉病菌,水稻纹枯病菌和苹果腐烂病菌的抑制活性相对较好,分别为64.75%、52.05%和69.68%;在药剂浓度为500mg/L时,化合物5d、5e和5f对TMV具有较好的治疗和钝化活性,其抑制率分别为56.93%和86.89%、53.08%和83.51%、53.40%和89.01%。以上研究结果表明,1,4-戊二烯-3-酮肟酯类化合物具有一定抑菌和抗病毒活性,在其结构基础上进行适当的改造,有望获得具有较高生物活性的有机分子。

Synthesis and Biological Activity of Novel 1,4-Pentadien-3-one Oxime Esters Bearing Heterocycle Moiety

In order to explore novel green pesticide with potent biological activities, a series of novel 1,4-pentadien-3-one oxime ester derivatives bearing heterocycle moiety, derived from curcumin, was designed and synthesized. Their structures were confirmed by infrared spectroscopy, proton nuclear magnetic resonance spectroscopy(¹H NMR), ¹³C NMR, and high resolution mass spectroscopy(HRMS). The bioassays indicate that inhibition rates of compound 5d against G.zeae, F.ox-ysporum and C.mandshurica at 50 mg/L are 64.75%, 52.05% and 69.68%, respectively, and compounds 5d, 5e and 5f have good curative and deactivation activities against tobacco mosaic virus at 500 mg/L, with the inhibition rates of 56.93% and 86.89%, 53.08% and 83.51%, and 53.40% and 89.01%, respectively. These indicate that 1,4-pentadien-3-one oxime ester is a valuable scafford to develope new compounds poessessing high biological activities such as potential antifungal and antiviral activities.