Key Laboratory of Biopesticide and Chemical Biology, Ministry of Education, Fujian Agriculture and Forestry University, Fuzhou 350002, China.
Molecules. 2018 Jun 21;23(7):1499. doi: 10.3390/molecules23071499.
A efficient 2-step protocol has been applied for the synthesis of Lansiumamide B (-methyl---styryl-cinnamamide, ) derivatives by various substitution on the amide nitrogen with alkyl, allyl, propargyl, benzyl or ester groups. The structures of nine new compounds were characterized by HRMS, ¹H NMR, and C NMR spectra. These compounds were tested in vitro against 10 strains of phytopathogenic fungi and showed a wide antifungal spectrum. The relationship between different substituents on the amide nitrogen and antifungal activity of Lansiumamide B derivatives were compared and analyzed. The result indicates that the length and steric hindrance of -substitution have a significant impact on biological activities. It is noteworthy that the methyl or ethyl substituent on the amide nitrogen is critical for the antifungal activities.
已应用一种高效的两步法方案，通过酰胺氮上的各种取代基（烷基、烯丙基、炔丙基、苄基或酯基）来合成 Lansiumamide B（-甲基---苯乙烯基肉桂酰胺）衍生物。通过高分辨质谱、1H NMR 和 13C NMR 谱对 9 种新化合物的结构进行了表征。这些化合物在体外对 10 株植物病原真菌进行了测试，表现出广泛的抗真菌谱。比较和分析了酰胺氮上不同取代基与 Lansiumamide B 衍生物抗真菌活性之间的关系。结果表明，-取代基的长度和空间位阻对生物活性有显著影响。值得注意的是，酰胺氮上的甲基或乙基取代基对于抗真菌活性至关重要。
