Article ; Online: Molecular basis of two pyrimidine-sulfonylurea herbicides: from supramolecular arrangement to acetolactate synthase inhibition.
2023 Volume 29, Issue 8, Page(s) 241
Abstract: Context: The design and synthesis of safe and highly active sulfonylurea herbicides is still a challenge. Therefore, following some principles of structure-activity relationship (SAR) of sulfonylurea herbicides, this work focuses on evaluating two ... ...
| Abstract | Context: The design and synthesis of safe and highly active sulfonylurea herbicides is still a challenge. Therefore, following some principles of structure-activity relationship (SAR) of sulfonylurea herbicides, this work focuses on evaluating two sulfonylurea derivatives bearing electron-withdrawing substituents, namely, -(CO)OCH Methods: All theoretical calculations were conducted using the highly parameterized empirical exchange-correlation functional M06-2X accompanied by the diffuse and polarized basis set 6-311++G(d,p). The atomic coordinates were obtained directly from the crystalline structures, and from the energies of the frontier molecular orbitals (HOMO and LUMO), chemical descriptors were obtained that indicated the influence of the functional groups in the sulfonylureas on the reactivity of the molecules. The intermolecular interactions in the crystals were analyzed using the Hirshfeld, QTAIM, and NBO surfaces. Toxicophoric modeling was performed by the PharmaGist webserver and molecular docking calculations were performed by the GOLD 2022.1.0 software package so that the ligand was fitted to the binding site in a 10 Å sphere. For this, genetic algorithm parameters were used using the ChemPLP scoring function for docking and ASP for redocking. |
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| MeSH term(s) | Molecular Docking Simulation ; Models, Molecular ; Acetolactate Synthase/chemistry ; Acetolactate Synthase/metabolism ; Herbicides/chemistry ; Herbicides/pharmacology ; Sulfonylurea Compounds/chemistry ; Sulfonylurea Compounds/pharmacology ; Pyrimidines |
| Chemical Substances | Acetolactate Synthase (EC 2.2.1.6) ; Herbicides ; Sulfonylurea Compounds ; Pyrimidines |
| Language | English |
| Publishing date | 2023-07-12 |
| Publishing country | Germany |
| Document type | Journal Article |
| ZDB-ID | 1284729-X |
| ISSN | 0948-5023 ; 1610-2940 |
| ISSN (online) | 0948-5023 |
| ISSN | 1610-2940 |
| DOI | 10.1007/s00894-023-05629-x |
| Database | MEDical Literature Analysis and Retrieval System OnLINE |
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