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New mono- and diesters with imidazoquinolinone ring- synthesis, structure characterization, and molecular modeling

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dc.title New mono- and diesters with imidazoquinolinone ring- synthesis, structure characterization, and molecular modeling en
dc.contributor.author Zarzyka, Iwona
dc.contributor.author Klásek, Antonín
dc.contributor.author Hęclik, Karol
dc.contributor.author Lyčka, Antonín
dc.contributor.author Bartošík, Radek
dc.contributor.author Dobrowolski, Lucjan
dc.relation.ispartof Molecules
dc.identifier.issn 1420-3049 Scopus Sources, Sherpa/RoMEO, JCR
dc.date.issued 2020
utb.relation.volume 25
utb.relation.issue 18
dc.type article
dc.language.iso en
dc.publisher MDPI AG
dc.identifier.doi 10.3390/molecules25184303
dc.relation.uri https://www.mdpi.com/1420-3049/25/18/4303
dc.subject ammonium thiocyanate en
dc.subject debenzylation en
dc.subject 3-hydroxyquinolinediones en
dc.subject thioxoimidazoquinolinone ring en
dc.subject molecular modeling en
dc.description.abstract The objective of the studies was to synthesize and characterize new mono- and diesters with an imidazoquinolin-2-one ring with the use of 2,3-dihydro-2-thioxo-1H-imidazo[4,5-c]-quinolin-4(5H)-ones and ethyl bromoacetate. The products were isolated at high yield and characterized by instrumental methods (IR, 1H-, 13C-, and 15N- NMR, MS-ESI, HR-MS, EA). In order to clarify the places of substitution and the structure of the derivatives obtained, molecular modeling of substrates and products was performed. Consideration of the possible tautomeric structures of the substrates confirmed the existence only the most stable keto form. Based on the free energy of monosubstituted ester derivatives, the most stable form were derivatives substituted at sulfur atom of enolic form the used imidazoquinolones. Enolic form referred only to nitrogen atom no 1. The modeling results were consistent with the experimental data. The HOMO electron densities at selected atoms of each substrate has shown that the most reactive atom is sulfur atom. It explained the formation of monoderivatives substituted at sulfur atom. The diester derivatives of the used imidazoquinolones had second substituent at nitrogen atom no. 3. The new diesters can be used as raw material for synthesis of thermally stable polymers, and they can also have biological activity. © 2020 by the authors. Licensee MDPI, Basel, Switzerland. en
utb.faculty Faculty of Technology
dc.identifier.uri http://hdl.handle.net/10563/1009941
utb.identifier.obdid 43881653
utb.identifier.scopus 2-s2.0-85091600473
utb.identifier.wok 000582046700001
utb.identifier.pubmed 32961776
utb.identifier.coden MOLEF
utb.source j-scopus
dc.date.accessioned 2020-10-05T13:46:34Z
dc.date.available 2020-10-05T13:46:34Z
dc.description.sponsorship TBU in Zlin [IGA/FT/2019/10]; Interdisciplinary Centre for Mathematical and Computational Modelling in Warsaw, Poland [G49-12]
dc.rights Attribution 4.0 International
dc.rights.uri http://creativecommons.org/licenses/by/4.0/
dc.rights.access openAccess
utb.ou Department of Chemistry
utb.contributor.internalauthor Klásek, Antonín
utb.contributor.internalauthor Bartošík, Radek
utb.fulltext.affiliation Iwona Zarzyka 1*, Antonin Klásek 2, Karol Hęclik 3, Antonin Lyčka 4, Radek Bartošík 2, Lucjan Dobrowolski 3 1 Department Organic Chemistry, Institution Rzeszów University of Technology, Powstańców Warszawy 6, 35-959 Rzeszów, Poland 2 Department Chemistry, Institution Tomas Bata University in Zlin, CZ-76272 Zlin, Czech Republic; klasek@utb.cz (A.K.); ra.bar@seznam.cz (R.B.) 3 Department Biotechnology and Bioinformatic, Institution Rzeszów University of Technology, Powstańców Warszawy 6, 35-959 Rzeszów, Poland; kheclik@prz.edu.pl (K.H.); ldobrowolski@prz.edu.pl (L.D.) 4 Research Institute for Organic Syntheses (VUOS), CZ-53354 Pardubice, Czech Republic; antonin.lycka@uhk.cz * Correspondence: izarzyka@prz.edu.pl
utb.fulltext.dates Received: 27 August 2020 Accepted: 17 September 2020 Published: 19 September 2020
utb.fulltext.sponsorship This research was funded by TBU in Zlin grant number IGA/FT/2019/10. and the research was funded by Interdisciplinary Centre for Mathematical and Computational Modelling in Warsaw, Poland grant number G49-12.
utb.wos.affiliation [Zarzyka, Iwona] Inst Rzeszow Univ Technol, Dept Organ Chem, Powstancow Warszawy 6, PL-35959 Rzeszow, Poland; [Klasek, Antonin; Bartosik, Radek] Inst Tomas Bata Univ Zlin, Dept Chem, CZ-76272 Zlin, Czech Republic; [Heclik, Karol; Dobrowolski, Lucjan] Inst Rzeszow Univ Technol, Dept Biotechnol & Bioinformat, Powstancow Warszawy 6, PL-35959 Rzeszow, Poland; [Lycka, Antonin] Res Inst Organ Syntheses VUOS, CZ-53354 Pardubice, Czech Republic
utb.scopus.affiliation Department Organic Chemistry, Institution Rzeszów University of Technology, Powstańców Warszawy 6, Rzeszów, 35-959, Poland; Department Chemistry, Institution Tomas Bata University in Zlin, Zlin, CZ-76272, Czech Republic; Department Biotechnology and Bioinformatic, Institution Rzeszów University of Technology, Powstańców Warszawy 6, Rzeszów, 35-959, Poland; Research Institute for Organic Syntheses (VUOS), Pardubice, CZ-53354, Czech Republic
utb.fulltext.projects IGA/FT/2019/10
utb.fulltext.projects G49-12
utb.fulltext.ou Department Chemistry
utb.fulltext.ou Department Chemistry
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