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Design, Synthesis, Safener Activity, and Molecular Docking of Novel N ‐Substituted Thiazide/Thiazole Derivatives
Author(s) -
Fu Ying,
Yi KeHan,
Li MingQiang,
Wang JingYi,
Chen YuFeng,
Ye Fei
Publication year - 2019
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.3393
Subject(s) - chemistry , thiazole , stereochemistry , proton nmr , docking (animal) , active site , bioassay , organic chemistry , enzyme , biology , genetics , medicine , nursing
A series of novel substituted thiazide/thiazole compounds were designed by splicing active groups and bioisosterism. The title compounds were synthesized via the cyclization, acylation, and carbamylation. All the compounds were characterized by IR, 1 H‐NMR, 13 C‐NMR, and HRMS. The single crystal of compound 3f was determined by X‐ray crystallography. The biological activity tests indicated that all the compounds showed potential safener activity to the herbicide chlorsulfuron, in which compound 3e showed almost the same level as the commercialized safener AD‐67. The molecular docking results were in good agreement with the bioassay results, which demonstrated that compound 3e might compete with chlorsulfuron in the acetolactate synthase active site, causing the herbicide ineffective in maize.