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dc.contributor.authorKijewska, Monika
dc.contributor.authorSharfalddin, Abeer A.
dc.contributor.authorJaremko, Lukasz
dc.contributor.authorCal, Marta
dc.contributor.authorSetner, Bartosz
dc.contributor.authorSiczek, Miłosz
dc.contributor.authorStefanowicz, Piotr
dc.contributor.authorHussien, Mostafa A.
dc.contributor.authorEmwas, Abdul-Hamid M.
dc.contributor.authorJaremko, Mariusz
dc.date.accessioned2021-03-14T11:48:43Z
dc.date.available2021-03-14T11:48:43Z
dc.date.issued2021-04-15
dc.identifier.citationKijewska, M., Sharfalddin, A. A., Jaremko, Ł., Cal, M., Setner, B., Siczek, M., … Jaremko, M. (2021). Lossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking. Frontiers in Chemistry, 9. doi:10.3389/fchem.2021.662533
dc.identifier.issn2296-2646
dc.identifier.doi10.3389/fchem.2021.662533
dc.identifier.urihttp://hdl.handle.net/10754/668107
dc.description.abstractThe 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).
dc.description.sponsorshipWe thank King Abdullah University of Science and Technology (KAUST) for their financial support. The simulation in this work were performed at King Abdulaziz University's High-Performance Computing Center (Aziz Supercomputer) (http://hpc.kau.edu.sa).
dc.language.isoen
dc.publisherFrontiers Media SA
dc.relation.urlhttps://www.frontiersin.org/articles/10.3389/fchem.2021.662533/full
dc.rightsArchived with thanks to Frontiers in Chemistry. Copyright © 2021 Kijewska, Sharfalddin, Jaremko, Cal, Setner, Siczek, Stefanowicz, Hussien, Emwas and Jaremko. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
dc.rights.urihttps://creativecommons.org/licenses/by/4.0/
dc.titleLossen Rearrangement of p-Toluenesulfonates of N-Oxyimides in Basic Condition, Theoretical Study, and Molecular Docking
dc.typeArticle
dc.contributor.departmentBiological and Environmental Sciences and Engineering (BESE) Division
dc.contributor.departmentBioscience Program
dc.contributor.departmentNMR
dc.identifier.journalFrontiers in Chemistry
dc.eprint.versionPublisher's Version/PDF
dc.contributor.institutionFaculty of Chemistry, University of Wrocław, Wrocław, Poland
dc.contributor.institutionDepartment of Chemistry, Faculty of Sciences, King Abdulaziz University, Jeddah, Saudi Arabia
dc.contributor.institutionDepartment of Chemistry Faculty of Science, Port Said University, Port Said, Egypt
dc.identifier.volume9
dc.contributor.affiliationKing Abdullah University of Science and Technology (KAUST)
pubs.publication-statusAccepted
kaust.personJaremko, Lukasz
kaust.personEmwas, Abdul-Hamid M.
kaust.personJaremko, Mariusz
refterms.dateFOA2021-03-14T11:48:43Z


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Archived with thanks to Frontiers in Chemistry. Copyright © 2021 Kijewska, Sharfalddin, Jaremko, Cal, Setner, Siczek, Stefanowicz, Hussien, Emwas and Jaremko. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.
Except where otherwise noted, this item's license is described as Archived with thanks to Frontiers in Chemistry. Copyright © 2021 Kijewska, Sharfalddin, Jaremko, Cal, Setner, Siczek, Stefanowicz, Hussien, Emwas and Jaremko. This is an open-access article distributed under the terms of the Creative Commons Attribution License (CC BY). The use, distribution or reproduction in other forums is permitted, provided the original author(s) and the copyright owner(s) are credited and that the original publication in this journal is cited, in accordance with accepted academic practice. No use, distribution or reproduction is permitted which does not comply with these terms.