N-苄氧甲酰基(苯)丙氨酸取代苯基酯的合成及生物活性测定

Synthesis and Bioactivity Studies on N-Benzyloxycarbonyl Alanine (Phenylalanine) Substituted-phenyl Esters

采用N,N'-二环已基酰二胺(DCC)和吡啶,以及DCC和4-(N,N-二甲氨基)吡啶(DMAP)分别形成的脱水缩合体系,N-苄氧甲酰基氨基酸和酚发生缩合反应生成了一系列结构新颖的N-苄氧甲酰基(苯)丙氨酸取代苯基酯.在DCC/DMAP体系中的反应产率大于在DCC/吡啶中的产率.用1HNMR,13CNMR,IR,MS和元素分析对目标化合物的结构进行了表征.对合成的目标化合物进行了初步的生物活性测试,结果表明目标化合物具有一定的杀菌活性和杀虫活性,杀菌活性高于杀虫活性.DL-丙氨酸芳基酯比相应的L-丙氨酸芳基酯的杀蚜虫活性要高.

A series of novel N-benzyloxycarbonyl alanine （phenylalanine） substituted-phenyl esters were synthesized by condensation reactions of N-Cbz-alanine （phenylalanine） with substituted phenols in the presence of N,N′-dicyclohexylcarbodimide （DCC） and pyridine, or DCC and 4-dimethylaminopyridine （DMAP）. The yields of the reactions in the presence of DCC and DMAP were higher than those in DCC and pyridine. The target products were characterized by ^1H NMR, ^13C NMR, IR, MS techniques and elemental analysis. A preliminary bioactivity test of the target products was performed, and the results showed that they exhibited moderate fungicidal activity and insecticidal activity, with the former being higher than the latter.