摘要
将α-蒎烯选择性氧化制备马鞭草烯酮,对羰基进行肟化和分离,再发生亲核取代反应,合成得到40个新型( Z )-/( E )-马鞭草烯酮肟醚(4a ~4t ,包括20对 Z / E 异构体),采用 1 H NMR、 13 C NMR 、FT-IR、UV-vis和ESI-MS对目标化合物进行了结构表征,并测试其抑菌活性。研究结果表明:在质量浓度50 mg/L下,目标化合物对8种植物病原菌均显示出不同程度的抑菌活性,其中化合物( E )- 4r (R=2,6-Cl)对苹果轮纹病菌的抑制率为77.8%,化合物( E )- 4s (R=2,6-F)对水稻纹枯病菌的抑制率为72.7%,化合物( E )- 4n (R= p -CN)对玉米小斑病菌的抑制率为70.8%,( Z )-/( E )-异构体对一些植物病原菌的抑制活性显示一定差异。建立了( E )-马鞭草烯酮肟醚化合物对水稻纹枯病菌抑制活性的CoMFA模型( r 2 =0.992, q 2 =0.507),进行3D-QSAR研究,结果表明建立的模型可用于设计具有潜在高活性的先导化合物。
Verbenone was prepared by selective oxidation of α-pinene at first. Then, by oximation of the carbonyl group ( Z )- and( E )-verbenone oxime compounds were synthesized and separaed, followed by the nucleophilic substitution reaction to afford forty novel ( Z )- and ( E )-verbenone oxime ether compounds 4a - 4t , including twenty couples of Z/E isomers. The structures of the target compounds were characterized by 1 H NMR, 13 C NMR, FT-IR, UV-vis, and ESI-MS. The antifungal activities of the target compounds were evaluated. The results showed that, at the mass concentration of 50 mg/L, all the target products exhibited certain inhibition activities against the eight kinds of plant pathogens. Compound( E )- 4r (R=2,6-Cl) had inhibition rates of 77.8% against Physalospora piricola . Compound( E )- 4s (R=2,6-F) had inhibition rates of 72.7% against Rhizoctonia solani. Compound ( E )- 4n (R= p -CN ) had inhibition rates of 70.8% against Helmithosporium maydis . Certain difference were found in inhibition activity of Z-E isomers against some plant pathogens. The CoMFA model( r 2 = 0.992 , q 2 =0.507) of ( E )-verbenone oxime ether compounds for inhibiting Rhizoctonia solani was established for the study of 3D-QSAR, and the results could provide a basis for the design of potential lead compounds with higher activity.
作者
王晓宇
段文贵
林桂汕
康国强
商明昊
雷福厚
WANG Xiaoyu;DUAN Wengui;LIN Guishan;KANG Guoqiang;SHANG Minghao;LEI Fuhou(College of Chemistry and Chemical Engineering, Guangxi University, Nanning 530004, China;Guangxi Key Laboratory of Chemistry and Engineering of Forest Products, Nanning 530008,China)
出处
《林产化学与工业》
EI
CAS
CSCD
北大核心
2019年第4期27-34,共8页
Chemistry and Industry of Forest Products
基金
国家自然科学基金资助项目(31560194)
广西林产化学与工程重点实验室开放基金资助项目(GXFC16-03)
广西大学大学生创新创业训练计划资助项目(201810593037)
