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Keywords = methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates

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14 pages, 4980 KiB  
Article
Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates
by Li-Xia Zhao, Hao Wu, Yue-Li Zou, Qing-Rui Wang, Ying Fu, Chun-Yan Li and Fei Ye
Molecules 2018, 23(1), 155; https://doi.org/10.3390/molecules23010155 - 12 Jan 2018
Cited by 6 | Viewed by 3691
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 [...] Read more.
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. Full article
(This article belongs to the Section Organic Chemistry)
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