Synthesis and Herbicidal Activities of Novel 4-(4-(5-methyl-3-arylisoxazol-4-yl)thiazol-2-yl)piperidyl Carboxamides and Thiocarboxamides

Molecules

De-Jin Hu¹  Su-Fang Liu¹  Tong-Hui Huang¹  Hai-Yang Tu¹ 

[1] Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China; E-mails

关键词: Heterocycles;    Piperidine-1-carboxamide;    Piperidine-1-thiocarboxamide;    D1 protease inhibitor;    Herbicide.;   

DOI  :  10.3390/molecules14031288

来源: mdpi

【 摘 要 】

A series of novel 4-(4-(5-methyl-3-arylisoxazol-4-yl)thiazol-2-yl)piperidyl carboxamides and thiocarboxamides were synthesized as potential lead compounds of inhibitors targeting D1 protease in plants. These compounds were designed on the basis of a D1 protease inhibitor hit structure identified by homology modeling and virtual screening. The syntheses of these compounds were accomplished via a four-step procedure including the isoxazole ring formation, α-bromination of acetyl group, thiazole ring formation, and carboxamide/thiocarboxamide attachment. The in vivo herbicidal activity tests show that most compounds possess moderate to good herbicidal activities. The enzyme activity of one compound against the native spinach D1 protease exhibits a competitive inhibition. The results suggest that these compounds are indeed potential inhibitors for targeting D1 protease in plants.

【 授权许可】

CC BY   
© 2009 by the authors; licensee Molecular Diversity Preservation International, Basel, Switzerland.