Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking
The sulfonic esters of N-oxyimides are a group of compounds with a wide range of biological activities, as well as a unique reactivity toward amines. They undergo this reaction with primary amines and other nucleophilic reagents according to a Lossen-like rearrangement. The reaction is initiated by...
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Frontiers Media S.A.
2021-04-01
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| Online Access: | https://www.frontiersin.org/articles/10.3389/fchem.2021.662533/full |
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| author | Monika Kijewska Abeer A. Sharfalddin Łukasz Jaremko Marta Cal Bartosz Setner Miłosz Siczek Piotr Stefanowicz Mostafa A. Hussien Mostafa A. Hussien Abdul-Hamid Emwas Mariusz Jaremko |
| author_facet | Monika Kijewska Abeer A. Sharfalddin Łukasz Jaremko Marta Cal Bartosz Setner Miłosz Siczek Piotr Stefanowicz Mostafa A. Hussien Mostafa A. Hussien Abdul-Hamid Emwas Mariusz Jaremko |
| author_sort | Monika Kijewska |
| collection | DOAJ |
| description | The sulfonic esters of N-oxyimides are a group of compounds with a wide range of biological activities, as well as a unique reactivity toward amines. They undergo this reaction with primary amines and other nucleophilic reagents according to a Lossen-like rearrangement. The reaction is initiated by nucleophilic attack on a carbonyl group in the succinimide ring followed by isocyanate formation, which next interacts with another nucleophile molecule forming an addition product (e.g., ureido or urethane derivative). However, the secondary amines are also susceptible to other reactions leading to products containing the maleimide ring formed by sulphonic acid elimination. In the case of tertiary amines, this reaction is predominant. To explain the phenomenon of the reactivity of the N- oxyimides toward different types of amines, we employed various spectroscopic and X-ray approaches as well as DFT calculation. Results suggest that the basicity of the amine used for the reaction plays a crucial role in the reaction mechanism that eventually dominates the entire chemical process. Moreover, we applied molecular docking to investigate the ability of the products to act as serine protease inhibitors using human leukocyte elastase (HLE). |
| first_indexed | 2024-12-20T10:37:33Z |
| format | Article |
| id | doaj.art-b101017c121e4572932dfc8aa6149a12 |
| institution | Directory Open Access Journal |
| issn | 2296-2646 |
| language | English |
| last_indexed | 2024-12-20T10:37:33Z |
| publishDate | 2021-04-01 |
| publisher | Frontiers Media S.A. |
| record_format | Article |
| series | Frontiers in Chemistry |
| spelling | doaj.art-b101017c121e4572932dfc8aa6149a122022-12-21T19:43:36ZengFrontiers Media S.A.Frontiers in Chemistry2296-26462021-04-01910.3389/fchem.2021.662533662533Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular DockingMonika Kijewska0Abeer A. Sharfalddin1Łukasz Jaremko2Marta Cal3Bartosz Setner4Miłosz Siczek5Piotr Stefanowicz6Mostafa A. Hussien7Mostafa A. Hussien8Abdul-Hamid Emwas9Mariusz Jaremko10Faculty of Chemistry, University of Wrocław, Wrocław, PolandDepartment of Chemistry, Faculty of Sciences, King Abdulaziz University, Jeddah, Saudi ArabiaDivision of Biological and Environmental Sciences and Engineering, King Abdullah University of Science and Technology, Jeddah, Saudi ArabiaFaculty of Chemistry, University of Wrocław, Wrocław, PolandFaculty of Chemistry, University of Wrocław, Wrocław, PolandFaculty of Chemistry, University of Wrocław, Wrocław, PolandFaculty of Chemistry, University of Wrocław, Wrocław, PolandDepartment of Chemistry, Faculty of Sciences, King Abdulaziz University, Jeddah, Saudi ArabiaDepartment of Chemistry Faculty of Science, Port Said University, Port Said, EgyptCore Labs, King Abdullah University of Science and Technology (KAUST), Jeddah, Saudi ArabiaDivision of Biological and Environmental Sciences and Engineering, King Abdullah University of Science and Technology, Jeddah, Saudi ArabiaThe sulfonic esters of N-oxyimides are a group of compounds with a wide range of biological activities, as well as a unique reactivity toward amines. They undergo this reaction with primary amines and other nucleophilic reagents according to a Lossen-like rearrangement. The reaction is initiated by nucleophilic attack on a carbonyl group in the succinimide ring followed by isocyanate formation, which next interacts with another nucleophile molecule forming an addition product (e.g., ureido or urethane derivative). However, the secondary amines are also susceptible to other reactions leading to products containing the maleimide ring formed by sulphonic acid elimination. In the case of tertiary amines, this reaction is predominant. To explain the phenomenon of the reactivity of the N- oxyimides toward different types of amines, we employed various spectroscopic and X-ray approaches as well as DFT calculation. Results suggest that the basicity of the amine used for the reaction plays a crucial role in the reaction mechanism that eventually dominates the entire chemical process. Moreover, we applied molecular docking to investigate the ability of the products to act as serine protease inhibitors using human leukocyte elastase (HLE).https://www.frontiersin.org/articles/10.3389/fchem.2021.662533/fullp-toluenesulfonatesN-oxyimidesXRDNMRDFTmolecular docking |
| spellingShingle | Monika Kijewska Abeer A. Sharfalddin Łukasz Jaremko Marta Cal Bartosz Setner Miłosz Siczek Piotr Stefanowicz Mostafa A. Hussien Mostafa A. Hussien Abdul-Hamid Emwas Mariusz Jaremko Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking Frontiers in Chemistry p-toluenesulfonates N-oxyimides XRD NMR DFT molecular docking |
| title | Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking |
| title_full | Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking |
| title_fullStr | Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking |
| title_full_unstemmed | Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking |
| title_short | Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking |
| title_sort | lossen rearrangement of p toluenesulfonates of n oxyimides in basic condition theoretical study and molecular docking |
| topic | p-toluenesulfonates N-oxyimides XRD NMR DFT molecular docking |
| url | https://www.frontiersin.org/articles/10.3389/fchem.2021.662533/full |
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