1. Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates
- Author
-
Ying Fu, Chun-Yan Li, Qing-Rui Wang, Yue-Li Zou, Hao Wu, Li-Xia Zhao, and Fei Ye
- Subjects
Stereochemistry ,Thiazolidine ,Pharmaceutical Science ,Ester hydrochloride ,01 natural sciences ,Zea mays ,Article ,Analytical Chemistry ,lcsh:QD241-441 ,chemistry.chemical_compound ,Acyl chloride ,lcsh:Organic chemistry ,Drug Discovery ,Cysteine ,Physical and Theoretical Chemistry ,methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates ,active substructure combination ,safener activity ,biology ,Molecular Structure ,010405 organic chemistry ,Herbicides ,Organic Chemistry ,Active site ,Esters ,Stereoisomerism ,04 agricultural and veterinary sciences ,Carbon-13 NMR ,Ketones ,0104 chemical sciences ,Molecular Docking Simulation ,Pyrimidines ,Sulfonylurea Compounds ,chemistry ,Design synthesis ,Chemistry (miscellaneous) ,Seeds ,040103 agronomy & agriculture ,Proton NMR ,biology.protein ,0401 agriculture, forestry, and fisheries ,Molecular Medicine ,Thiazolidines - Abstract
A series of novel methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates were designed by active substructure combination. The title compounds were synthesized using a one-pot route from l-cysteine methyl ester hydrochloride, acyl chloride, and ketones. All compounds were characterized by IR, 1H NMR, 13C NMR, and HRMS. The structure of 4q was determined by X-ray crystallography. The biological tests showed that the title compounds protected maize from chlorimuron-ethyl injury to some extent. The ALS activity assay showed that the title compounds increased the ALS activity of maize inhibited by chlorimuron-ethyl. Molecular docking modeling demonstrated that Compound 4e competed against chlorimuron-ethyl to combine with the herbicide target enzyme active site, causing the herbicide to be ineffective.
- Published
- 2018