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Molecules 2018, 23(1), 155; doi:10.3390/molecules23010155

Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates

College of Science, Northeast Agricultural University, Harbin 150030, China
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Received: 20 December 2017 / Revised: 5 January 2018 / Accepted: 12 January 2018 / Published: 12 January 2018
(This article belongs to the Section Organic Synthesis)
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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. View Full-Text
Keywords: methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates; active substructure combination; safener activity methyl (R)-N-benzoyl/dichloroacetyl-thiazolidine-4-carboxylates; active substructure combination; safener activity
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This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. (CC BY 4.0).

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Zhao, L.-X.; Wu, H.; Zou, Y.-L.; Wang, Q.-R.; Fu, Y.; Li, C.-Y.; Ye, F. Design, Synthesis, and Safener Activity of Novel Methyl (R)-N-Benzoyl/Dichloroacetyl-Thiazolidine-4-Carboxylates. Molecules 2018, 23, 155.

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