1,4-戊二烯-3-酮肟醚类化合物的合成及生物活性

将1,4-戊二烯-3-酮结构中的羰基转变为肟醚基团,合成了7个1,4-戊二烯-3-酮肟醚类化合物,其结构经1H NMR、13C NMR、IR和ESI-MS表征。生物活性测试结果表明,在药剂浓度为500mg/L时,化合物4c、4f和4g对烟草花叶病毒(TMV)在治疗作用方面的抑制率为49.6%、53.6%和47.4%,与病毒唑(45.2%)相当;化合物4b、4c、4f和4g对TMV在保护作用方面的抑制率分别为57.2%、58.4%、58.9%和59.0%,稍低于病毒唑(61.8%);化合物4a、4b、4c和4g对TMV在钝化作用方面的抑制率分别为95.5%、92.6%、95.0%和89.5%,优于对照药病毒唑(87.9%)。这些结果表明,1,4-戊二烯-3-酮肟醚类化合物对植物病毒表现有良好抑制作用,在其结构基础上进行适当的优化,有望得到具有良好抗植物病毒活性的先导化合物。

Synthesis and biological activities of penta-1,4-diene-3-one Oxime ether Derivatives

Seven novel penta-1,4-diene-3-one oxime ether derivatives, which were confirmed by IR, 1H NMR, 13C NMR and ESI-MS, were synthesized by converting carbonyl groups in the 1,4-pentadien-3-ones to an oxime ether groups. Antiviral bioassays at 500 mg/L indicated that compounds 4c, 4f,and 4g exhibited better curative activity against tobacco mosaic virus (TMV) (49.6, 53.6 and 47.4%, respectively) than ribavirin (45.2%); that protective activities of compounds 4b, 4c, 4f and 4g against TMV were respectively 57.2, 58.4, 58.9 and 59.0%, which were lower than that of ribavirin (61.8%); and that inactivition activities of compounds 4a, 4b, 4c and 4g against TMV were respectively 95.5, 92.6, 95.0 and 89.5 %, which were superior to that of ribavirin (87.9%). These results indicated that penta-1,4-diene-3-one oxime ether derivatives had good inhibitory effect against plant virus, and that some compounds with potent anti-plant viral activities can be obtain based on properly modifications on structures of penta-1,4-diene-3-one oxime ethers.