Synthesis and fungicidal activity study of novel daphneolone analogs with 2,6-dimethylmorpholine  

作　　者：Gao-Fei Xu Xin-Ling Yang Peng Lei Xi-li Liu Xue-Bo Zhang Yun Ling 

机构地区：[1]Department of Applied Chemistry, College of Science, China Agricultural University [2]Department of Plant Pathology, College of Agronomy and Biotechnology, China Agricultural University

出　　处：《Chinese Chemical Letters》2016年第4期555-558,共4页中国化学快报（英文版）

基　　金：supported by the National Natural Science Foundation of China (No. 21272266);the National High Technology Research and Development Program of China (No. 2011AA10A202)

摘　　要：A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one（I） from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR,1H NMR, and HRMS（ESI） or elemental analysis,13 C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method.All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 mmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure–activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.A series of novel daphneolone analogs was designed and synthesized on the basis of natural product 1,5-diphenyl-2-penten-1-one（I） from Stellera chamaejasme L. as lead compound, whereby 2,6-dimethylmorpholine moiety was introduced to replace 1-phenyl group. Their structures were confirmed by IR,1H NMR, and HRMS（ESI） or elemental analysis,13 C NMR for some representative compounds. The two isomers of target compounds were separated and identified by NOESY technique and chemical method.All of the synthesized compounds have been evaluated for anti-plant pathogenic fungi activities. The results showed that some compounds exhibited moderate to good antifungal activities against tested fungi at the concentration of 50 mg/L. Among them, compound 7d, with a 4-bromine-substituted phenyl group and cis-2,6-dimethylmorpholine moiety, displayed best activity with an EC50 of 23.87 mmol/L against Valsa mali, superior to lead compound I. In addition, preliminary structure–activity relationship analysis indicated that, between two isomers of target compounds, the antifungal activities of the isomer with cis-2,6-dimethylmorpholine were better than the trans-isomer.

关 键 词：Daphneolone analogs 2.6-Dimethylmorpholine Stellera chamaejasme L. SYNTHESIS Fungicidal activity 

分 类 号：TQ455[化学工程—农药化工]