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Molecules 2009, 14(3), 1288-1303; doi:10.3390/molecules14031288

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

Key Laboratory of Pesticide & Chemical Biology, Ministry of Education, College of Chemistry, Central China Normal University, Wuhan 430079, P. R. China
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Received: 27 February 2009 / Revised: 12 March 2009 / Accepted: 16 March 2009 / Published: 24 March 2009
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Abstract

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, a-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.
Keywords: Heterocycles; Piperidine-1-carboxamide; Piperidine-1-thiocarboxamide; D1 protease inhibitor; Herbicide Heterocycles; Piperidine-1-carboxamide; Piperidine-1-thiocarboxamide; D1 protease inhibitor; Herbicide
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MDPI and ACS Style

Hu, D.-J.; Liu, S.-F.; Huang, T.-H.; Tu, H.-Y.; Zhang, A.-D. Synthesis and Herbicidal Activities of Novel 4-(4-(5-methyl-3-arylisoxazol-4-yl)thiazol-2-yl)piperidyl Carboxamides and Thiocarboxamides. Molecules 2009, 14, 1288-1303.

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